Characters / A Series of Unfortunate Events (2017) – Antagonists

The antagonists of the 2017 adaptation of Lemony Snicket's A Series of Unfortunate Events.

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Count Olaf

Count Olaf

Count Olaf and his many disguises.^note Right column, top to bottom: Captain Sham, Detective Dupin, Stephano, Shirley. Bottom row, left to right: Coach Genghis, Mattathias Medicalschool, Gunther.

Portrayed By: Neil Patrick Harris

The Baudelaire children's (geographically) closest living relative, who tricked Poe into giving him custody in order to get at the fortune. Though the children manage to escape from him, he now relentlessly pursues them, donning disguises to fool those around them and killing anyone who dares to get in his way.

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• Abusive Parents: Plays this role when the Baudelaires are living with him, from trying to put a wedge between them and Justice Strauss so she'll stop asking questions to hitting Klaus. He also has abusive adoptive parents in the form of the Man With a Beard But No Hair and the Woman With Hair But No Beard.
• Adaptational Attractiveness: Hook nose and unibrow aside, he's still played by the very attractive Neil Patrick Harris.
• Adaptational Dumbass: Somewhat. The book/movie versions of Olaf are seriously Book Dumb, but dangerously cunning and good at thinking on his feet. Here he's about as dim and ignorant as his previous incarnations, but he's also much, much, much, much worse at disguising himself to the point where the Baudelaire children are not the only ones to see through them (several VFD members were also able to see through them too). He even brings his entire theater troupe with him for his schemes while in disguise, rather than just bringing one or two of them (which they proved to actually fool the Baudelaires much more often in the novels than it did in the TV Series).
• Adaptational Intelligence: While Olaf isn't very good with dealing with escaping without the help of his henchmen in this version, he is also, at times, considerably more capable than his book counterpart. He's able to more closely follow the Baudelaires wherever they go, and certain things that might have tricked him in the book don't work in the series, such as Klaus' doctor disguise in Hostile Hospital.
• Adaptation Personality Change: Due to this, as well as a change in general story framing, Count Olaf comes off just ever so slightly more sympathetic in this version. In the books, Olaf is unrelentingly cruel and unpleasant start to finish apart from one significant Pet the Dog moment that's so far and away from the character the audience has been shown that it's bewildering. In contrast, in the tv show he displays more moments of melancholy and vulnerability while still being an undeniably terrible person: He genuinely seems to show signs of hesitation, and then remorse for killing Jacques. Later on, he's shown to be desperate for the approval of the Man with a Beard but no Hair and the Woman with Hair but no Beard, who are revealed to have manipulated Olaf into becoming who he is today after scouting him out when he was emotionally fragile after the death of his father.
• Adaptational Wimp: While Olaf was usually fearless in the book, in the TV series, he's scared by the lions in the carnival and in one truly pathetic moment, by an Iguana.
• Alas, Poor Villain: Olaf spends the latter half of "The End" dying from blood loss from a harpoon. While it is extremely karmic for him to die in this way, it is incredibly sad to watch him die next to the woman he loves. He also carries her to safety in his last moments, saving her daughter's life. The Baudelaires themselves, seeing their Arch-Enemy dying, are brought to tears.
• The Alcoholic: Empty bottles are littered around Olaf's house, and he seems to carry wine with him while tailing the Baudelaires. Sunny outright calls him a lush, a word which here means drunkard.
• And Now You Must Marry Me: He tries this on Violet in the second episode. His motive seems to be purely financial, but there are a couple lines that imply his intentions may be even grosser than that. After all, he does say he wouldn't dispose of Violet after the wedding... (Shudder.)
• Anti-Hero: During his time in VFD. Aunt Josephine mentions he used to burn ants with a magnifying glass, and the flashback at the opera house portrays him as crass, snarky, and judgmental as opposed to the other members' polite eloquence. Jaques points out that, despite these traits, he was still a hero who "helped put out many fires".
• Aristocrats Are Evil: Has the title Count, and is trying to steal the Baudelaires' fortune.
• At Least I Admit It: During his testimony at the hotel, he tears into all the adults who are supposedly trying to "help" the Baudilaires, telling them that while he may have made their lives hell, he was at least honest about his selfishness.
• Bad "Bad Acting": He's not a very good actor, to say the least. But he's still able to trick people with disguises.
• Bad Boss: He's not only a cruel and demanding boss, but also a terribly inept one. So much so that his troupe often hits him with backtalk for dumping all his cheap(er) boxed wine on them and giving out orders with vague parameters.
• Big Bad: His plot to steal the Baudelaire fortune is directly responsible for most of the orphans' misery.
• Big Eater: He eats massive amounts of food, even eating entire roasts on his own and buying a massive tub of popcorn just for himself and giving a tiny one for the kids while in disguise and going to a movie.
• Big Ol' Eyebrows: His large one gray eyebrow curling inwards and to the sides, befitting both his comical buffoonery and his (poorly) hidden sinister nature.
• Book Dumb: Does not know the difference between "literally" and "figuratively", but manages to outsmart most of the adults in the series, mainly because they're even dumber than he is.
• Bunny-Ears Lawyer: Subverted. As evil as he is, and as blisteringly terrible as his actual stage acting skills are, he is quite good at getting into character for all the disguises he uses throughout the series (the only times he ever seems to slip up are when he gets mad or one of his henchpeople screws something up), but the Baudelaires can see right through his disguises, and the only people they seem to work on are adults more stupid or willfully ignorant than he normally is. Granted, in the later episodes, Olaf stops trying to fool the children with his disguises, as shown with his Gunther disguise. When the Baudelaires first see this disguise, he talks to them in his regular voice, likely because he knows they'll just see right through it anyway.
• …But He Sounds Handsome: Does this constantly. While disguised, he seems to be unable to mention Count Olaf without heaping on the compliments (even when his persona should never have met Olaf) and cannot tolerate insults toward his appearance or acting ability. Naturally, to anyone besides the kids, his own accomplices, and some VFD members, this does not give him away.
• Card-Carrying Villain: He outright admits being a bad guy. Boastfully in fact.
  Count Olaf: Your first impression of me may be that I am a terrible person. But in time, Baudelaires, I hope you'll come to realize... you haven't the faintest idea.
• The Charmer: On a very superficial level, that only works because Adults Are Useless. Before he's outed in The Bad Beginning, he gives Justice Strauss the opprotunity to fulfill her dreams as an actor, to distract her from the fact he's using her to marry Violet. Then in his disguises, he flatters Aunt Josephine, Vice Principal Nero, Sir, and others to get them on his side against the orphans. He even calls out Strauss and Nero during his testimony at the hotel.
• Child Hater: Hates the Baudelaires in particular, but also clearly despises children in general.
• Clark Kenting: His disguises are usually little more than wigs and costumes.
• Comic-Book Fantasy Casting: Neil Patrick Harris has admitted that he based Count Olaf's numerous alter-egos on real people or other fictional characters; Captain Sham's lisping Scottish brogue is an impression of Sean Connery, Stefano's demeanor and body language resemble those of Peter Lorre, Coach Genghis' voice was based on that of John B. McLemore from S-Town, Gunther looks and acts just like Karl Lagerfeld, and Inspector Dupin's demeanor was described as a mix between Jason Mraz and Chester Cheetah.
• Deadpan Snarker: There's absolutely shades of it with almost everything he says having some sort of putdown toward the one he's talking to or even after some of his most evil acts using a sort of bleak one liner to rub salt on the wound.
• Death Equals Redemption: Subverted. While he does carry Kit to safety and spends his last moments tenderly reciting a poem with her, he also makes it clear that he doesn't regret anything he did and never asks the Baudelaires for forgiveness.
• Death Glare: Whenever something ticks him off. Sometimes comes complete with growling.
• Deuteragonist: Since the series expands past the Baudilaires' point of view, the audience spends almost equal time with him plotting and preparing for his disguises as we do with them. In a strictly storytelling sense, his B-Plots in the first half of most episodes place him as a protagonist going after what he wants, and Jaqueline, Jaques, or Larry as the antagonist attempting to foil him.
• Devil in Plain Sight: The children pick up on it almost immediately.
• Did They or Didn't They?: What did Nero mean when he said, "He didn't stroke my ego! He only stroked my... violin."
• Dies Wide Open: He ends up dying with his eyes open unlike in the novel, where he dies with his eyes closed.
• Dirty Coward: He's scared away during the end of The Reptile Room by an iguana and orders his henchmen to distract the police so he can make a clean getaway.
• Dirty Old Man: While he was primarily marrying her for her family’s fortune, Olaf states that he will be able to touch whatever he pleases as he grabs Violet’s shoulder, implying he has other sinister intentions for her after they get married.
• Equal-Opportunity Evil: The fact that he has two elderly women, a handicapped man with hooks for hands, and a person of indeterminate gender in his crew would seem to point to him being this; it doesn't matter what you are so long as you kowtow to his manic whims. The Baudelaires wonder if giving these people a place to be when no one else would is the reason why they are so loyal to him.
• Even Bad Men Love Their Mamas: Judging from the way he describes his short stint at Prufrock Preparatory School, Olaf was always kind of a jerk even before he left the VFD. But the breaking point for him was the night of the opera: Beatrice Baudelaire accidentally killed Olaf's father while trying to steal Esmé Squalor's sugar bowl.
• Even Evil Has Loved Ones: When things are going good for them at least, he actually shows genuine affection to both Georgina and Esme. Even stronger with Kit, his true love; when he hears she might die, he braves through a harpoon wound to carry her to safety and spends his dying moments reciting poetry with her.
• Even Evil Has Standards: Olaf is, without a doubt, one of the worst villains. However, even he ends up loathing Carmelita Spatts. And of course, he attempts to save Kit from dying.
  • The sight of the Great Unknown approaching on the Sonar is enough for Olaf to react in complete terror, ordering Fernald to turn out the lights and forcing Carmelita to keep quiet with a hand over her mouth. Apparently, tangling with the Great Unknown is a step too far for him.
• Evil Is Hammy: Oh, yes! Grandiose Evil Gloating, Evil Laughs that wouldn't be out of place in one of Neil Patrick Harris' other gigs, the occasional musical number... Even when he's in disguise as someone who should be taking things seriously, he can't resist chewing on the scenery. But then again, Count Olaf is a terrible actor.
• Evil Is Petty:
  • Forces the orphans to do all of his household chores and then eats the roast lamb that Justice Strauss made for them. And tells her they didn't like it to turn her against them.
  • When Violet asks him to pass the pot stickers, he instead eats them all and says they're all gone.
  • After hitchhiking with a truck driver, he repays him with a chocolate bar wrapper.
  • He forces Klaus and Violet to eat corn while they're disguised as conjoined twins so he can laugh at them struggling to do so.
• Evil Redhead: Flashbacks reveal that he had red-brown hair in his youth, and sunlight will bring some reddish tint in the present.
• Fallen Hero: While it was always implied that he was part of the VFD, it's outright confirmed during "The Vile Village" that he was not only a member, but a very respected one, even by Jacques.
• Faux Affably Evil: There are multiple points where the cold, murderous side of Olaf comes to forefront. Examples include threatening to cut off Sunny's toes or murdering Monty.
• Forgotten Childhood Friend: Weaponized. He often finds himself up against his ex-allies from VFD, but because they never cared for him all that much and barely paid attention to him after he left, he's able to hide his identity from them with ridiculously transparent disguises.
• The Friend Nobody Likes: It's implied that he's absent in every Secret Society Group Picture of his former VFD cell, because he's the one stuck taking the photographs. His former compatriots in the organization never cared much about him, finding many of his mannerisms immature and his intellect lacking, and even Lemony, the member he was closest to, grew to despise him the most. On the other hand, Jacques, in trying to get Olaf to come back to the good side of the schism in "The Vile Village", tells him that he still admires and respects him despite what he's become.
• Giftedly Bad: He considers himself a very handsome man and an incredibly talented and famous actor, when he is neither.
• Have I Mentioned I Am Heterosexual Today?: Needs to be assured that he isn't a sissy just because he is an actor, gets hung up on dandier matters, and sometimes has to dress in drag. He also stresses that he can charm the pants off of any beautiful woman of his choosing, even though he's so far only found success with middle-aged women and those on his payroll and somehow manages to ignore Esmé's blatant flirting.
• Hero Killer: Despite his incompetence, he is directly or indirectly responsible for more deaths on the show than even some of the more ruthless characters. He personally kills Uncle Monty and Jacques Snicket and causes the deaths of Aunt Josephine, Olivia Caliban, Larry Your-Waiter, and Dewey Denouement, as well as (possibly) the Baudelaire parents and likely several people in the Hotel Denouement fire.
• Illegal Guardian: He takes the children in, but plots to steal their fortune.
• Insistent Terminology: Gets very tetchy when Jacqueline addresses him as "Mr. Count Olaf". As he explains, it's redundant, and Count is his title.
• It's Personal:
  • While the prime motivation is old fashioned Greed, it is implied that Olaf's plot to ruin the Baudelaire Orphans is also to get the last laugh on their late parents.
  • This becomes his primary motive in season 2. It's pointed out that Olaf doesn't really even need the Baudelaire's fortune anymore as he can just live off his extremely wealthy Dark Mistress, but he's obsessed with hunting them down anyway and at one point tells a captive Violet he will destroy her and her siblings in the cruelest manner imaginable. This isn't an empty threat, either, as the following episodes have him doing things like trying to force Klaus to decapitate Violet, attempting to feed them to starved lions, and dropping Violet and Klaus off a cliff after abducting Sunny.
  • We finally learn the whole story near the end of the show: Beatrice accidentally killed his father when a fight broke out over their stealing Esmé Squalor's sugar bowl, starting him on the path to villainy.
• I Regret Nothing: When he saves Kit's life, she points out that this won't make her forgive every evil thing he's done. He dryly points out that he hasn’t apologised.
• I Take Offense to That Last One: Though Olaf may willingly admit he's a terrible person with ease, he will proceed to gasp dramatically and be insulted if you call him a bad actor. as showcased here.
• Jerkass: Even beyond the murder, subterfuge, and cruelty, Olaf is really unpleasant. He's petty, antagonistic, and has an insult for almost everyone he meets.
• Just a Stupid Accent: Uses ridiculous accents when in disguise. Especially as Stephano.
• Kavorka Man: As in the books, despite his poorly groomed and somewhat unattractive appearance, to say nothing of his awful personality, he has no difficulty attracting no less than four beautiful women (Dr. Orwell, Josephine, Esmé, and Kit Snicket) over the course of the series. Also, half of his henchfolk are in love with him.
• Knight of Cerebus: Whenever he's on screen, things tend to get a lot darker. to the point that even moments that are meant to be comedic in nature take on a discomforting and sinister vibe.
• Know-Nothing Know-It-All: While he's clearly not stupid, he's also not nearly as cultured or as book smart as he likes to pretend he is.
• Large Ham: Overacts his lines and mannerisms as an actor.
• Laughably Evil: Menacing but quite over-the-top and comical.
• "L" Is for "Dyslexia": Besides the aforementioned "figuratively" and "literally" dilemma, during his troupe's performance of "The Count" in "The Bad Beginning", he links the letters of his name to a virtue he supposedly has... right up to reaching the N which he links to "knowledge". He also constantly confuses certain words, doesn't know the meaning of others or mispronounces them. Given his general lack of academic smarts, it would be safe to say he has barely a basic grasp on vocabulary other than what he's heard. One of the main complaints Aunt Josephine has about his speech in "The Wide Window, Part 2" is not his attempts to take the children (well, also that), it's his misuse of "have".
• Lean and Mean: He's tall, skinny, and an utter bastard.
• Line-of-Sight Alias: How he came up with the alias Yessica Haircut: a glance at a "haircut" appointment on a calendar, and a long "yessss" when questioned about it.
• Looks Like Orlok: While not a vampire, Olaf bears many resemblances to the nosferatu of German cinema. His balding head, his hooked nose, his aged and dirty clothes that may have been fancy and refined once. In his mannerisms, Olaf moves from one setting to another, sowing chaos and death just as the vampire did, taking on disguises and killing innocent people all for his hunt for what does not belong to him. It does not help that two of his three targets just so happen to be women. Even his name - Count Olaf - sounds a lot like Count Orlok.
• Lorre Lookalike: Olaf's first alter-ego, Stefano, was confirmed by Neil Patrick Harris to be an impression of Peter Lorre; while the accent is different, being distinctly Italian instead of vaguely Eastern-European, Stefano still has the same reedy voice, unusual body language, and creepy mannerisms of a typical Lorre character.
• Manipulative Bastard: Is able to manipulate others through flattery and threats.
• The Masochism Tango: His and Georgina's romantic history is described in segments of passion and betrayal, and when the two collaborate in the modern day, they quickly devolve into bickering and insults.
• Motive Decay: Originally after the Baudelaire fortune, he gives up on this in the latter half of the second season and becomes obsessed with killing them for the sake of it. Justified, as it's implied that the repeated failures of his schemes are causing Sanity Slippage, which is made even worse by finding out that one of the Baudelaire parents might still be alive.
• Named by the Adaptation: Mattathias, his disguise in "The Hostile Hospital", is given the surname "Medicalschool" (pronounced "meh-dickle-school").
• Narcissist: As in the books and the film, but even those incarnations didn't have a song about how great they were!
• Never Learned to Read: Considering his poor understanding of grammar (such as his failure of understanding the intentional grammar errors in Aunt Josephine's fake suicide note, which she took advantage of) and his general disregard and incomprehension of certain large words. See also Book Dumb and "L" Is for "Dyslexia" for some other examples.
• Not Me This Time: In "The End," he insists he didn't kill the Baudelaire parents, and he actually seems sincere for once. Given that he's dying and has nothing left to lose, there's no reason for him to have lied.
  • Also, at the time the Quagmire Mansion is being burned down, he is in Paltryville, disguised as Shirley, so he can't have been personally responsible for it.
• Obfuscating Stupidity: He's Wicked Pretentious and he does not know the difference between "literally" and "figuratively", but signs point to him being not nearly as dumb as he presents himself to be. He is able to masterfully manipulate an overwhelming majority of the adults in his way with his disguises (which admittedly, isn't very hard), he was able to find the orphans multiple times without the VFD's extensive resources and support and before he dies, he was able to recite a poem he had memorized for Kit Snicket years prior. One does not become a member of the Volunteer Fire Department (banned or not) without some level of intelligence, after all.
  • It is very likely that he actively suppresses some of his more favorable traits due to his willfully antagonistic relationship with the organization that favors such traits.
• Obviously Evil: Well, he's a creepy, shady looking guy with a decrepit, filthy house whose demeanor masks a deep resentment and real menace regarding the Baudelaire orphans and insists on insulting them referring them as orphans. Yep, nothing shady about this guy, huh, Poe?
• Offscreen Moment of Awesome: Somehow managed to capture two lions offscreen in "The Carnivorous Carnival".
• Out of Focus: In "The Erszats Elevator", the audience doesn't see him prepping for his confrontation with the Baudelaires like in most episodes, as that would ruin The Reveal that Esme is willingly in cahoots with him.
• Paper-Thin Disguise: The Baudelaires have no trouble seeing through his disguises. Some of them, such as his Stephano disguise, are at least passable, but most of the time he just puts on an outlandish outfit that barely conceals his distinctive looks.
• Politically Incorrect Villain: He describes the orphans' meal as "disgusting foreign food", calls short people "midgets" and "pygmies", and points out that not complaining about her chores is a good quality in a wife. And of course, there's his constant disparagement of orphans in general.
• Psychopathic Man Child: Aptitude for scheming aside, Count Olaf has all the qualities: unrelenting selfishness and pettiness, no patience or control of his temper to speak of, a need to be the center of attention even when it's not beneficial, and refusing to do any tasks that he can pass off to someone else. These traits become amplified after his Villainous Breakdown.
• Pyromaniac: Enjoys setting fires, calling it his hobby. Seems to have had this trait since even before the schism, as a flashback shows him setting an opera curtain on fire before catching himself and snuffing it out.
• "The Reason You Suck" Speech: While on trial at the Hotel Denouement, he tears into the many adults whose greed, cowardice, pettiness, and all-around uselessness allowed him to get as far as he did.
• Revenge Before Reason:
  • In the second season, upon reuniting with Esmé Squalor, he gets the opportunity to acquire the massive fortune he was originally after, but by that point, he's too furious at the Baudelaires to give up hunting them. (Although they may not be able to draw from said fortune now that she's a wanted criminal)
  • In "The Slippery Slope" The Man With A Beard But No Hair and The Woman With Hair But No Beard chastise him for this, wasting his time chasing after the Baudelaires and allowing them to repeatedly get the better of him when he could have been going after easier, more lucrative targets.
• Small Name, Big Ego: He takes great pride in his minuscule theatrical accomplishments, although it's implied that he's aware of how few and puny they are.
• Smug Snake: The only reasons his plans even have a chance of succeeding is because all the adults are very stupid.
• The Sociopath: He's a remorseless manipulative mass murderer who has a huge ego, cares for no-one but himself and will steal and kill to satisfy his own materialistic desires. He's also charismatic enough to lead his own gang. Olaf's a low-functioning example however as his superficial charm is unconvincing and his disguises only work due to most of the adults being incredibly dumb. He also, despite being impulsive and brash since his youth, didn't seem to become that calloused and evil until his father's death and grooming by the Fire-Starting side.
• Surrounded by Idiots: He has a very low threshold for the buffoonery of others. At the same time, he constantly insists on the mental inferiority of the much more intelligent and resourceful Baudelaires.
• Took a Level in Jerkass: He was always despicable, but he becomes even eviler after the events of "The Hostile Hospital". Lampshaded in the Expository Theme Tune for "The Carnivorous Carnival", which notes that "Count Olaf is the worst he's been for more than several weeks".
• Tranquil Fury: Drops into this when something really ticks him off. He stops yelling, goes quiet and calm, he may even smile... and then people get hurt.
• Uncleanliness Is Next to Ungodliness: Has poor hygiene and his home is a shambling pigsty.
• Upper-Class Twit: More Twit than Upper Class, however.
• Villain Protagonist: In most of the Part 1 B-Plots. Unlike the books, the series steps out of the Baudilaires' point-of-view to show his struggles to set his disguise/plans into motion before putting him face-to-face with heroes in Part 2. His actor also gets top-billing and is most prominent in promotional material.
• Villainous Breakdown: After meeting The Man With A Beard But No Hair and The Woman With Hair But No Beard, who proceed to chastise him for not living up to their expectations, Olaf's confidence shatters and he behaves more like a sulky, angry, petulant child for the rest of the series.
• Villainous Crush: He appears to be attracted to Violet, but is really only interested in her because he wants the fortune and may have only creeped on her to intimidate her and Klaus.
  • A Freeze-Frame Bonus in "The Vile Village" shows that he scrawled Josephine's name along with Georgina's, Esme's, and Kit's on a barroom table in his youth. This shows that despite it being an act by the time of The Wide Window, he did have a thing for her at one point. This is different from his other love interests, as she seems to have always viewed him as despicable.
• Villain's Dying Grace: Played with; like in the books, Count Olaf's final moments humanize him more than anything. It certainly doesn't redeem him from all the evil deeds he did, as Kit doesn't forgive him, nor does he ask to be forgiven, but his final act does show him capable of genuine love, compassion, and even a bit of poetic depth.
• Villainous Glutton: His greed and hedonism extend to his appetites as he eats huge amounts of food and leaves only scraps for everyone else and thinks he's performing an act of kindness even doing that.
• Villain Song: You can't have Neil Patrick Harris play a villain without giving him a few songs.
  • "It's the Count" from "The Bad Beginning" has him boasting about how glorious and talented he is, while his theater troupe provides the music and backup vocals.
  • "Keep Chasing Your Schemes" from "The Ersatz Elevator" is an upbeat "motivational" song that Olaf is forced to sing (by Larry and Jacqueline, specifically) in order to entertain the patrons at Herring Houdini. Unbeknownst to him, this is meant to distract him while the Baudelaires search for the Quagmires in the elevator shaft.
  • "House of Freaks" from "The Carnivorous Carnival" has Olaf (now a ringmaster) flaunting the bizarre qualities of his freaks, while simultaneously humiliating them.
• We Used to Be Friends: He used to be friends with the Baudelaire parents and the Snicket siblings, particularly Lemony and Kit. Then something happened that made them the bitterest of enemies. It's eventually revealed that Beatrice accidentally killed his father during the fight over her and Lemony stealing the sugar bowl from Esmé.
• "Well Done, Son" Guy: He tries to make his treacherous deeds look impressive to his surrogate parents, the Man with a Beard but no Hair and the Woman with Hair but No Beard.
• Wicked Cultured: In The Grim Grotto, his submarine has a wine cabinet on it and he's shown to have good taste in wine, including Cabernet Sauvignon. He doesn't know how to pronounce it however. Generally speaking he's ...
• Wicked Pretentious: He lives in a huge house, is part of a theater troupe, frequently uses big words, and drinks wine. But the house is filthy and falling apart, he's an awful actor, he clearly doesn't know what a lot of the words mean, and it's boxed wine. He's also rather Book Dumb, which undermines the effect even further.
• Would Hurt a Child: Does not care if the Baudelaires are harmed or killed, so long as one of them survives to give him the fortune.
• You Killed My Father: In "The Penultimate Peril" we learn that Beatrice Baudelaire accidentally killed his father.

Esmé Squalor

Esmé Gigi Geniveve Squalor

"I'll learn your names later."

Portrayed By: Lucy Punch

A woman obsessed with what's "in" and "out", who adopts the Baudelaires once orphans become in. She turns out to be in cahoots with Count Olaf and has a long standing anger towards the Baudelaire's mother, Beatrice, regarding a mysterious Sugar Bowl that seems to have started everything.

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• Adaptational Dye-Job: The book illustrations portray her with dark hair, while in the show, she's a blonde.
• Adaptational Modesty: Interestingly, her outfit in "The Penultimate Peril" is much less revealing than the one described in the books. ^note  Which consisted of three pieces of lettuce stuck to her body with tape She even references this.
• Adaptational Villainy: The ending of Season 1 implies that she is the one who started the Quagmire Fire^note while the culprit is never revealed, the hat they are wearing matches up with one Esme wears in the book. Additionally, the nature of the fires implies that she is also the one who started the Baudelaire fire. The books never connect her to either of these arsons.
• Awesome, but Impractical: The knife-tipped heels that Esmé wears in "The Hostile Hospital" are a zig-zagged example. While they are difficult and uncomfortable to walk in and keep getting stuck in the floor, they are still extremely effective when they are used as throwing knives.
• Ax-Crazy: Esmé is deranged, violent and uncontrollable when pushed to the edge, especially when related to the Sugar Bowl, much more so than the Count and physically, she tends to be much more dangerous and ruthless than him, quickly resorting to weaponry and physical violence, which so far has included a harpoon gun and heels with blades.
• Bitch in Sheep's Clothing: At first. Despite being bossy and snobbish, she seemingly believes the children when they warn her about Olaf, only to reveal her true colors moments later by throwing them down an elevator shaft.
• Clingy Jealous Girl:
  • She really doesn't like the idea of Madame Lulu getting close with Olaf. It gets to the point where she tries to get one of the carnival freaks to kill Lulu just to get her out of the picture.
  • And when she hears Olaf mention Carmelita, she immediately declares a desire to scratch her eyes out. Olaf is taken aback by this, and has to clarify he's talking about a child.
• Connected All Along: Count Olaf was her acting teacher, and she was in the plan all along. She also is related to Beatrice, who she claims to have stolen from her.
• The Dragon: The most unhinged and threatening ally to Count Olaf shown yet. He also doesn't have as much control over Esmé and she can and often will act as an independent agent while chasing her own plans, including her relationship with Olaf and obtaining her Sugar Bowl.
• Dragon with an Agenda: The Baudelaire and Quagmire fortunes are just a positive consequence of her quest. What she wants more than anything is her missing Sugar Bowl and is even willing to go over Count Olaf's plans for it, such as releasing Olivia and Jacques at the cost of revealing its location and proposing to release the orphans from the hospital if they give it to her.
• Even Evil Has Loved Ones: For all her unpleasantness, she genuinely adores Carmelita and treats her like a daughter. She was also a loyal and loving girlfriend towards Olaf. She also never actually harms Jerome, bar knocking him out to get him out of the way of things, when she joins Olaf; she easily could have done.
• Evil All Along: She doesn't actually care for the children and was in on Olaf's plan from the start.
• Evil Brit: Played by English actress Lucy Punch, who uses her natural accent as Esmé — though Count Olaf thinks her accent is fake.
• Evil Costume Switch: Following her reveal that she is working with Count Olaf, she drops her white clothes, she is clad in black and dark gray clothes, using black lipstick during the auction.
• Evil Is Hammy: Lucy Punch is clearly having a blast in the role. Special mention goes to her stint as Officer Luciana.
• Evil Is Petty: Her own personal motivation for tormenting the Baudelaires? She believes their mother stole a sugar bowl from her years ago.
  • Her ultimate revenge? Tricking everyone at Olaf's trial into literally eating crow that she and Carmelita ground into sausages and made with too much black pepper.
• The Fashionista: Seen in a wide variety of outfits in almost every episode she appears in, bordering on Unlimited Wardrobe.
• Fun with Acronyms: Her name Esmé Genevive Gigi Squalor spells out Eggs, but in the Vile Village episodes she also uses several pseudonyms that spell out words like Spam or Cute with the initials.
• It's Personal: The reason she's after the Baudelaires? She believes Beatrice stole the Sugar Bowl from her, despite the fact Lemony Snicket did.
• Karmic Death: If she did in fact die in the hotel fire while searching for the Sugar Bowl, it was a very fitting end considering how remorselessly she was willing to hurt others just to get it.
• Knight of Cerebus: Once she becomes a part of the villain's troupe, the show takes a significantly darker route, and the Baudelaires are often in the middle of genuine and gruesome physical harm, including threats of being burned alive and almost forcing Klaus to saw Violet's head off. Count Olaf even states that he is no longer satisfied with only taking their fortune, but also wants to kill them, which seems to be partially Esmé's own Ax-Crazy influence.
• Left Stuck After Attack: She, at one point, uses high heels with blades in the place of heels, meant to be used as weapons, however, they are extremely thin and hard to walk on, rendering them not that useful because they keep getting stuck in openings on the floor. They are though, much more useful when she uses them as throwing knifes.
• Light Is Not Good: Most of her clothes tend to be white, and she's a thoroughly evil person.
• Woman Of Wealth And Taste: She has really expensive tastes and is obsessed with what's "in" and what's "out", often buying expensive things just because.
• Misplaced Retribution: She gets dumped by Count Olaf, so she takes it out on the guests of Hotel Denouement by making them choke on crow sausage.
• More Deadly Than the Male: Olaf isn't exactly harmless, but Esmé is slightly less prone to theatrics and more willing to just get the job done, especially when it comes to getting revenge on all good VFD agents and getting the Sugar Bowl. Olaf might have the biggest body count, but Esmé is the one most certain to kill the right person or to get close to getting what she wants. This eats away at their relationship, since it catches the attention of The Man With A Beard but No Hair and The Woman With Hair but No Beard and they start relying more on her than Olaf, which creates an unequal partnership.
• Ms. Fanservice: A warped version of this trope. She's very attractive and some of her dresses are quite impressive, if a little absurd and tacky. Combine this with her personality, however, and neither ends up mixing well.
• Narcissist: Even more than Olaf!
• Never Bareheaded: She's almost always seen wearing hats, and they're all very fancy ones, even if some are absurd.
• Outlaw Couple: With Count Olaf.
• The Reveal: She's in cahoots with Count Olaf and wants the Baudelaire fortune too.
• Rich Bitch: She's an incredibly wealthy, yet completely psychotic bully.
• Right for the Wrong Reasons: Believes that Beatrice stole her sugar bowl. Lemony actually did it, but Beatrice was fully on board with that plan.
• Sadist: She gives a satisfied smile when Olivia falls to her death in the lion pit.
• Silk Hiding Steel: She's a Proper Lady who doesn’t hesitate to use violence against her enemies, even going so far as to try and crush the Baudelaires to death with a filing cabinet.
• Skewed Priorities: The real reason she's psychotically hell-bent on the Sugar Bowl, the very reason she turned on the Snickets and has ruthlessly hunted the Baudelaires? It completes her tea set.
• Small Name, Big Ego: Always introduces herself as the city's sixth most important finacial advisor like it's a high societal position.
• The Sociopath: A high-functioning version, unlike her boyfriend.
• Uncertain Doom: Like several other characters, it is not revealed whether she survived the fire at Hotel Denouement. Although, considering she was last seen being tricked into heading to the laundry room (where the fire was started) by Olaf, her chances aren't good.
• Unlimited Wardrobe: Lampshaded by Olaf when she manages to pull together a ridiculous octopus costume from seemingly out of nowhere in a matter of seconds.
• Unwitting Instigator of Doom: If you take into account the night of the Opera, Esmé kick-started the Schism that lead to the Sugar Bowl theft and the death of Olaf's father. How? She refused to allow VFD to use her Sugar Bowl to store the cure for Medusoid Mycelium in it because it was part of her tea set. The result lead to her throwing a poison dart at Kit and Lemony after they stole it and leading to Beatrice accidentally hitting Olaf's father with another.
• Villainous Legacy: Just as with Dr. Georgina Orwell, Esmé is a former girlfriend of Count Olaf's and an ex-member of VFD, on the villainous side of the Schism. She also has a grudge against the Baudelaire parents, specifically Beatrice, who supposedly stole her infamous sugar bowl and its unknown contents. Ironically, she has no idea that the Sugar Bowl was actually stolen by Lemony Snicket, meaning her vendetta against the Baudelaire family is entirely pointless. Though, while Lemony does blame himself for fallout over the sugar bowl, as stealing it was his idea, it's revealed that Beatrice was in fact involved with the theft as well.
• Wicked Cultured: Always immaculately dressed, well-spoken, attends the fanciest restaurants and has very expensive tastes. It's unclear as to how much is her own taste and how much is just her following the latest trends however.
• We Used to Be Friends: Like Olaf, she used to friends with Beatrice and Lemony until the incident with the sugar bowl.

The Sinister Duo

The Man with a Beard but No Hair and The Woman with Hair but No Beard

The Man with a Beard but No Hair Portrayed By: Richard E. Grant

The Woman with Hair but No Beard Portrayed By: Beth Grant

A pair of menacing villains first encountered on the Mortmain Mountains. Described as having such a strong aura of menace that even Olaf fears them.

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• Abusive Parents: Abusive adoptive parents to Count Olaf.
• Adaptational Intelligence: In the books, they have no idea what a Verdant Flammable Device is and give one to Esmé that Sunny is later able to use to signal Violet and Klaus. In the show, they instantly recognise the object and call Olaf an idiot for letting Sunny use it.
• Adaptational Jerkass: They're lot meaner to Olaf than they were in the books, which makes his willingness to kill them along with everyone else in the Hotel Denouement more understandable.
• The Bad Guy Wins: "The Slippery Slope" ends with them successfully kidnapping the Snow Scouts and murdering every single one of their parents in a mass house burning. It's one of the grimmest endings in the whole series.
• Bad Is Good and Good Is Bad:
  Woman: Typical Olaf, throwing a party instead of starting a fire.
  Man: And after we tried so hard to set a bad example.
• Bald of Evil: The Man with A Beard but No Hair, naturally. Does not apply to the Woman with Hair but No Beard.
• Beard of Evil: Again, the Man with A Beard but No Hair. Also does not apply to the Woman with Hair but No Beard.
• Card-Carrying Villain: They shame Olaf’s evil deeds because they were not evil enough.
• The Corruptor: Their modus operandi is to find people at their most vulnerable (sometimes after tragedies they engineered) and lay on some classic emotional manipulation to twist them into minions. Olaf was one of their projects. They also serve as High Court Judges as well, allowing their influence to reach endlessly.
• Dramatic Irony: The Woman with Hair but No Beard tells Olaf that he's disappointed them for the last time shortly before their implied death via the fire in the hotel.
• The Dreaded: They give off an aura of menace, one strong enough that Lemony is still terrified of them years later, when they might very well be dead, and even strong enough that a person can recognise it over the phone. Even Olaf is terrified of them.
• Evil Brit: The Man with A Beard but No Hair is played by British actor, Richard E. Grant, has the accent, and is very, very evil.
• Evil Sounds Deep: The Woman with Hair but No Beard's voice drops a few octaves when she gets seriously angry.
  Esmé: (after being told to do something) Why should we do it?
  Woman: Because we said so, that's why!
• Greater-Scope Villain: They were the heads of the dark side of V.F.D. even prior to the Schism, and they turned Count Olaf into the villain he is today.
• If You're So Evil, Eat This Kitten!: They command Olaf to prove his villainy by murdering Sunny Baudelaire, in an attempt at severing his fixation on the Baudelaire family. Hilariously, Olaf can't go through with it... not because he cares about Sunny or has any moral qualms about murdering a toddler, but just because he still really wants their fortune.
• Karmic Death: It's implied by their final scene that their sheer refusal to believe in Count Olaf ultimately does them in after the very trial they were rigging. Though initially impressed with the prospect of him burning down the hotel, they immediately disbelieve it after with no sign of further consideration seen, putting them likely in the camp of those who didn't run from the fire. Thus, this would be karmic on both fronts, both killed because of the very VFD member who they turned to evil, and in a fire just like the countless ones they'd started.
• Kick the Dog: They murder the circus freaks for no real reason, beyond seeing whether Olaf will care. He doesn't.
• Knight of Cerebus: Just like they were in the book, the series gets much much darker, and Olaf's behaviour changes. Also, unlike Esmé, herself a Knight of Cerebus, there's absolutely nothing humorous about them.
• No Name Given: Lemony Snicket refuses to give their names, because he's so terrified of them.
• Not Helping Your Case: They insist they're not emotionally distant or abusive to Olaf. He's just never done anything to earn their approval.
• Parental Favoritism: Or Parental Substitute Favoritism, in this case. They make it clear they immensely prefer Esmé to Olaf from the minute they meet her.
• Phrase Catcher: Everyone describes them as "the man with a beard but no hair" and "the woman with hair but no beard", even a character who just talks to them on the phone. The fact that these are the attributes they're referred to by is justified in the series by the Man's beard and the Woman's hair being almost identical in shape.
• Pyromaniac: Fire is their solution to everything.
• Related in the Adaptation: Here, they're Olaf's adopted parents.
• Small Role, Big Impact: They only appear in three episodes, but they were the ones who molded Olaf into a psychopathic pyromaniac, all-but orchestrated the Schism from behind the scenes, and are the leaders of the evil side of the V.F.D.
• Uncertain Doom: Like several other characters, it is not revealed whether they survived the fire at Hotel Denouement.
• Villain with Good Publicity: Their jobs are as judges. Nobody suspects them at all of being evil, just highly sinister and terrifying.

Count Olaf's Theater Troupe

In General

• Adaptational Dumbass: The entire theater troupe proves to be a lot less competent in this version than they were in the novels, in which Lemony Snicket himself concedes that like Olaf, they are quite intelligent. There disguises prove to be much more paper thin than they were in the novels and they often screw up during Olaf's schemes.
• Adaptational Heroism: The Bald Man and the Person of Indeterminate Gender leave alongside the Powder-Faced Women after deciding they had enough of Count Olaf’s cruelty, while in the books, they were loyal to him until their deaths. Additionally, the Hook-Handed Man cares for Sunny and helped save her life without bartering his aid for the Baudelaires and Fiona taking him with them during their escape. In the books, he complained about Sunny making his life miserable and helped purely out of selfish reasons.
• Adaptational Nice Guy: Many of them come across as significantly less cruel, and those who were already given sympathetic traits show them earlier on. The standout here goes to the Henchperson of Indeterminate Gender, but it applies to nearly all of them to some extent, and the Powder-Faced Women are the only ones this really doesn't apply to at all.
• Adaptation Expansion: Their personalities are much more fleshed out in this show than in the books and the film.
• Alternate Character Interpretation: In-universe, the Baudelaire children start to wonder, at the end of Season 2, whether they are with Count Olaf because they're evil, or simply he is the only one that will offer them a place to be and treat them with some semblance of humanity. Season 3 goes with the latter interpretation.
• Bad "Bad Acting": They're just as bad as Olaf at acting. The final episode reveals that, without Olaf as their teacher, the Powder-Faced Women, Bald Man, and Henchperson of Indeterminate Gender all went on to some success as actors.
• Dumb Muscle: None of them are particularly smart and they all are willing to get their hands dirty when helping Olaf.
• Dwindling Party: Like the books, all of them disband themselves from the troupe, leaving Olaf alone by The End. However, this adaptation changes it up a bit. Both the Henchperson of Indeterminate Gender and the Bald Man are spared from their original fates in ''The Hostile Hospital'' and ''The Carnivorous Carnival'' respectively, instead survive long enough to defect from Olaf's troupe alongside the Powdered-Face Women in The Slippery Slope. Ironically enough, the Carnival Freaks are unceremoniously killed by Olaf's superiors instead of surviving and sticking around up until their original unknown fates in The Penultimate Peril. The Hook-Handed Man, Esme Squalor, and Carmelita Spats's departure from the troupe (Fernald's reunion with Fiona, Olaf breaking up with Esme and disowning Carmelita) remains unchanged though.
• Earn Your Happy Ending: All of the original troupe abandon Olaf and thus get happier endings than he does. The Bald Man, Powder-Faced Women and Henchperson of Indeterminate Gender become celebrated theater actors while Fernald is reunited with his sister and stepfather.
• Even Evil Has Standards: They all have moments when they show shock and horror at Olaf's actions. All but Fernald quit when Olaf wants them to dump Sunny off a cliff.
• Gentle Giant: Their three tallest members: Bald Man, Hook-Handed Man and Henchperson of Indeterminate Gender are the least evil but help make the team seem more intimidating as a group.
• No Name Given: Even when talking about each other or themselves they never reveal their names. Subverted in Season 3, which reveals the Hook-Handed Man's name is Fernald.
• Paper-Thin Disguise: All of their disguises are easy to see through except the Foreman. This can be fairly considered a case of Pragmatic Adaptation: Olaf's associates in the books, including Esmé, were historically better than he was at fooling the Baudelaires with their disguises – usually not even being revealed to the reader until the end of each story – but it's one thing to carry off a trick like that on the page when you can make descriptions of characters as ambiguous as you like, and another to do it onscreen with recognizable actors.
• Screw This, I'm Out of Here!: The Powder-Faced Women, Bald Man and Henchperson of Indeterminate Gender all abandon Olaf after he tries to order them to kill Sunny. The Hook-Handed Man also leaves a few episodes later after being reunited with his sister.
• Slasher Smile: When they kidnap Larry.
• The Pirates Who Don't Do Anything: Played with. Due to the nature of Olaf's plans they do a lot of (admittedly bad) acting but they don't perform in actual productions outside of The Marvelous Marriage and a briefly mentioned audition.

The Hook-Handed Man

Fernald / The Hook-Handed Man

Portrayed By: Usman Ally

One of Count Olaf's minions, he has hooks for hands. He is also capable of understanding Sunny.

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• Adaptational Nice Guy: His bond with Sunny is entirely absent from the books, and he only saves her life in The Grim Grotto because Fiona asked him to. Here, he saves Sunny without hesitation before he even knows the Baudelaires are with Fiona, and he's pretty much the Token Good Teammate of Olaf's troupe for the majority of the series.
• Affably Evil: He can be quite friendly at times, and later forms an Odd Friendship with Sunny.
• Artificial Limbs: His hooks from the book are replaced with more realistic prosthetics.
• Ambiguously Bi: He stayed with Olaf while the rest of the troupe leaves. In the same episode after the Powder-Faced Women exclaimed they were in love with Olaf and the Bald Man says that he's in love with Esmé, Fernald says that he's in love but is cut off before he can say who.^note Usman Ally goes on to state that he interprets The Hook-Handed Man to have some kind of love for Olaf but leaves it to interpretation on whether the feeling was romantic or intensely grateful. However, he also is hinted to be turned on by Collette's contortions during the "House of Freaks" number.
• Anti-Villain: Becomes significantly more sympathetic once his backstory as a former agent of VFD who got kicked out for doing a bad thing for a noble reason is revealed, and his love for his sister Fiona eventually outweighs his loyalty to Olaf. To emphasize this, he's the one to tell the Baudelaires that the world is not comprised of Black-and-White Morality like they think, but Grey-and-Gray Morality.
• Ascended Extra: While the Hook-Handed Man has always been one of the more prominent members of Olaf's troupe in the books he was never implied to be anything more than just another member for Olaf to use when he felt like it. Here he's upgraded into being Olaf's Dragon and is the member of the troupe with the most screentime. He even sometimes gets scenes or roles that other minions got in the books.
• Bald of Evil: Downplayed. He works for Count Olaf and is portrayed by bald actor Usman Ally, but he's seemingly one of the least evil members of the troupe.
• Big Brother Instinct: Despite being evil, he shows great care for the baby Sunny, holding his hands out in fear that Olaf would drop her during "The Bad Beginning", and goes to check on the flour-bag Sunny after Olaf kicks his foot through it in the "Austere Academy". As of season 2 after Madame Lulu tells him that his sister depends on him he wonders to himself whether or not he should call her.
• Cloudcuckoolander: He gets childishly excited about chocolate pudding; is very fond of Sunny and understands her perfectly; and didn't realize that the bag of flour Olaf kicked wasn't Sunny after it exploded.
• Cumbersome Claws: While his prosthetics are far more useful than typical hooks for hands, they can still be incredibly cumbersome at times, and he often has difficulty with grabbing/holding objects. Occasionally, he has to hold objects in his mouth while trying to place them into his prosthetic hands.
• The Dragon: Seems to be Olaf's right hand man, or at least the closest thing to one, as he is often given the more important tasks (keeping an eye on the children usually) and is usually seen as the one bossing around the other members of Olaf's Troupe.
• The Driver: Interestingly, he's the guy who drives the group's car.
• Even Evil Has Standards: When Olaf is dangling Sunny from over the kitchen table, his first instinct is to try and reach for her in case she falls, implying he has at least some slightly better morals than his boss.
  • He did commit arson, only because VFD'sGregor Anwhistle was developing what can only be described as a WMD in his lab.
• Evil Cripple: He's funny, but so unrepentantly wicked that you'd be forgiven for not feeling too sorry for the various difficulties his... condition burdens him with. Although he becomes significantly more sympathetic in Season 3.
• Foreshadowing: He looks visibly worried after Madame Lulu mentions his sister in "The Carnivorous Carnival: Part 1". This sets up the events of "The Grim Grotto", where he does indeed reunite with his little sister, Fiona.
  • He's also much nicer to the Baudelaires (most notably Sunny). This foreshadows that he isn't so evil.
  • "I wanted to be a marine biologist."
• Good Scars, Evil Scars: He has several facial scars.
• Graying Morality: Formerly a member of the noble side of VFD, Fernald's resolve to fight fire with fire caused him to take on a very gray outlook on life, deciding that no one was entirely good or bad.
• Hypocritical Humor: He believes that you shouldn't go easy on children and that they should be taught to respect their elders in spite of his highly dysfunctional relationship with his own father.
• Kick the Dog:
  • During his time as Foreman Flacutono he's noticeably more unpleasant, bossing around and hassling the various members of the Lucky Smells Mill and breaking Klaus's glasses vindictively. Even if he is Just Following Orders, he's still pretty dickish about it. This is probably a holdover from the way Foreman Flacutono was originally written in the fourth book, being played there by the bald long-nosed man, who in the books is a thoroughly sinister Jerkass with no redeeming qualities whatsoever. (In contrast, the books' hook-handed man, while certainly wicked, is a bit more restrained and was actually pleasant in his role as the doorman at 667 Dark Avenue.)
  • He's also the one that made Larry wash the dishes when holding him captive.
• Ironically Disabled Artist: Despite his double case of Hook Hand, he plays the piano. Badly.
• Lighter and Softer: His hooks look more like prostheses that could be found in real life than the nightmarish things they were presented as in previous media.
• Lima Syndrome: Or "Mount Fraught Syndrome", as Lemony's narration refers to it. He genuinely starts to care for Sunny the longer Olaf holds her prisoner on Mount Fraught which is why he secretly lets her out of the birdcage while Olaf is distracted by the rest of the troupe quitting.
• Love Redeems: His love for his sister greatly outweighs his loyalty to Olaf, leading to Fernald finally abandoning him for good.
• Malevolent Masked Men: As Foreman Flacutono, he disguises himself in a gas mask. Not only does it prevent the kids from immediately finding him out, but as the Foreman he's at his most intimidating and the inability to see his face adds to that.
• Mistreatment-Induced Betrayal: Olaf, Esmé and Carmelita mock him quite cruelly for not being a part of their "family", which presumably influences him to help the Baudelaires and then ditch his old cohorts when he reunites with his actual family, his sister Fiona.
• Mythology Gag: He wears a fedora and trenchcoat for his disguise in "The Reptile Room", a nod to his outfit of choice in the original books.
• No Good Deed Goes Unpunished: He was kicked out of VFD when he set his partner's lab on fire to kill the Medusoid Mycelium that he was cultivating. Said partner was going to use the deadly and easily airborne fungi as a biological weapon to kill the organization's enemies.
• Noble Demon: Overlapping with Stupid Evil. When he begins playing poker with Sunny out of sheer boredom, their escalating bets (and Sunny's talent at cards) mean that he eventually is forced to free her and transport her onstage in a wheelbarrow, while wearing her gag taped over his own mouth.
  Hook: But, boss, she had a straight flush!
• Odd Friendship: With Sunny, most clearly in Season 2, where his first response to seeing her where she shouldn't be is to have a casual chat with her. Later, his response to the Henchperson of Indeterminate Gender asking if the baby was driving the firetruck out of the Village of Fowl Devotees is to respond, with pride in his voice, that she's more like a toddler at this point.
• Only Sane Man: For Olaf's troupe. While he certainly had more than a bit of a childish Cloudcuckoolander streak, he does seem to have more common sense than the other members of the troupe, and is generally the one who makes the most reasonable objections or points out the most obvious flaws in Count Olaf's logic. Not that anyone pays him any mind.
• Race Lift: In most of the illustrations for the books the Hook-Handed man is portrayed as white in the series he's portrayed by Swazi-born Pakistani actor Usman Ally (see Token Minority).
• Spared by the Adaptation: In the books, he and his family shared an Uncertain Doom alongside the Quagmires and Hector, but this incident is deleted from the series and we instead see an optimistic shot of Fernald and Fiona resolved to find their stepfather.
• Suddenly Fluent in Gibberish: For reasons unknown, he is the only person besides Violet and Klaus who can understand Sunny's baby talk. Interestingly enough, in the books, the only people who could completely understand Sunny (other than the Baudelaire children) were usually unambiguously good and intelligent—the Quagmire triplets, Captain Widdersins, and Fiona are just three examples. Considering the Hook-Handed Man is Fiona's brother, it's not a stretch to think that there's some good left in him, which is eventually confirmed in Season 3.
• Token Minority: He's the only member of Olaf's troupe to be non-white.
• Took a Level in Jerkass: He's noticeably less pleasant to the Baudelaires when being the new foreman for the Lucky Smells Mill, breaking Klaus's glasses and trying to get him into trouble. This is a result of his role being expanded; in the book the bald man was Foreman Flacutono, not him.
• Took a Level in Kindness: Conversely, he is portrayed in a much lighter fashion in Season 3, thanks to his Odd Friendship with Sunny and later being reunited with his sister.
• Wouldn't Hurt a Child: Downplayed. He's willing to put Violet and Klaus through absolute hell, and seems to have no objections to his boss trying to kill them, but he is somewhat protective of Sunny, who's only a baby.
  • Even Evil Has Standards / Pragmatic Villainy: He didn't see any point in sending Klaus and Violet to their doom.

The Powder-Faced Women

The Powder-Faced Women

Portrayed By: Jacqueline And Joyce Robbins

Twins who are two of Count Olaf's minions.

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• Age Lift: Elderly, in contrast to previous depictions.
• Cloudcukoolander: One of them mentions sometimes drinking a glass of vinegar when she thinks nobody watching.
• Didn't Think This Through: They're two old ladies that try to kidnap Uncle Monty, a physically active middle-aged man, by themselves under Count Olaf's orders. Predictably, it doesn't go well for them.
• Evil Old Folks: Older then the rest of the troupe by several decades, they are usually the most mean-spirited towards the Baudelaire twins.
• Even Evil Has Loved Ones: They have (or had going off of the books' examples) another sister too, according to their reactions to "Madame Lulu's" fortune reading. It turns out their sister is indeed dead, as well as their parents.
• Even Evil Has Standards: It's probably hard to see but when Olaf is dangling Sunny from over the dining table, the Hook-Handed Man and the Powder-Faced Women were the ones stretching their arms upward towards Sunny. In season 3, they outright abandon Olaf when he demands they throw Sunny off a cliff, having just found out that they lost their parents and probably their sister the same way the Baudelaires and the Quagmires did and promptly leave. This is true to their characters in the books - who were also the least "villainous".
• Ignored Enamored Underling: The compliments the twins heap upon Count Olaf suggest they have affection for him as well as loyalty. Like everyone else he doesn't bother to ignore or kill, Olaf considers them to be nothing more than tools in his arsenal. Even after they decide to leave, they tell Olaf they love him but are not going to kill Sunny or help him any further.
• My God, What Have I Done?: They seem to have a variant of this when they realize they may have unwittingly been aiding the organization that was responsible for killing their parents and sister.
• Professional Butt-Kisser: Most of the time.
• Screw This, I'm Outta Here: When they learn they've been working with the people who destroyed their family and when Olaf orders them to kill Sunny.
• Single-Minded Twins: Very much so, to the point that they finish each other's sentences and are always standing side-by-side.
• The Dividual: Of the Twindividual kind. They are nearly-identical (being twins) and they're effectively one character.

The Bald Man

The Bald Man

Portrayed By: John De Santis

One of Count Olaf's minions, he is one of the less intelligent of the theater troupe—and that's saying something.

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• Adaptation Personality Change: A significant one, combining Adaptational Dumbass and Adaptational Nice Guy under the synthesis of Dumb Is Good. The bald man with the long nose in the books is Olaf's most menacing henchman, arguably even more so than Olaf himself due to his wickedness never being Played for Laughs, and is an enormous Jerkass to the Baudelaires while under disguise in book four. The series' equivalent is much more physically intimidating, but is significantly less intelligent and generally comes across as a dimly agreeable guy who lacks the wherewithal to pose much of a threat. He also sports a somehow-endearing Villainous Crush on Esmé.
• Adaptational Name Change: In the books he was called "The Bald Man with a Long Nose" for obvious reasons. In the show, he's just called "The Bald Man" since his actor doesn't have a long nose. Which is a little bit awkward since the Hook-Handed Man is also bald.
• Bald of Evil: It's right there in his name.
• Beware the Silly Ones: He's mostly the Dumb Muscle of the group, but he's still very large and very strong. He's been proven capable enough to physically subdue both Jacquelyn and Jaques Snicket on separate occasions. Even Olaf looks scared when he thinks he's about to physically attack him before abandoning him.
• The Brute: By virtue of being the physically largest henchperson.
• Demoted to Extra: In The Miserable Mill book, the Bald Man was the one who played the role of Foreman Flacutono. In the show he's replaced by the Hook-Handed Man and the Bald Man doesn't appear in that story at all.
• Evil Is Bigger: Is the tallest member of the theater troupe, standing 6'9".
• Evil Sounds Deep: Has a deep, baritone voice, and definitely counts as evil.
• Hidden Depths: As shown in "Carnivorous Carnival: Part One", he's apparently an amazing artist, if his portrait of Esmé is to be believed.
• The Quiet One: The least talkative of the troupe.
• Spared by the Adaptation: Doesn't fall into the lion pit, and still alive at the end of Season 2. Instead, he simply abandons Olaf along with the White-Faced Women and the Henchperson of Indeterminate Gender.
• Villainous Crush: Calls Violet a "pretty little one." Also develops one for Esmé in Season 2.

The Henchperson of Indeterminate Gender

The Henchperson of Indeterminate Gender

Portrayed By: Matty Cardarople

The last member of Count Olaf's theater troupe, they seem unaware of what is happening most of the time.

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• Adaptational Attractiveness: The Henchperson of Indeterminate Gender in the books was described as being a hulking figure, which was a large factor in their gender being unclear, and their appearance was framed as frightening and uncanny because of it. In the series, they're portrayed more as an average person who doesn't conform to a specific gender and they aren't framed as bizarre or eerie for it.
• Adaptation Name Change: In the books, this henchperson was called "The Henchperson That Looks Like Neither a Man Nor a Woman." The series, like the 2004 film, instead uses the shorter epithet "The Henchperson of Indeterminate Gender".
• Adaptational Wimp: While their character in the book wasn't as defined, they acted as the muscle for the gang and at one point was able to restrain all three of the orphans at once on their own and even resist Sunny's bites. In show they're much less physically imposing and all together not that focused on whatever task was given to them.
• Affably Evil: They're less malicious than the others and they were the only one that was somewhat nice to Larry.
• Ambiguous Gender: Per the name, the Henchperson's gender is unclear, with them displaying both masculine and feminine traits. Here, it's implied that their ambiguity is part of a nonconforming gender identity, and not a vague and frightening appearance as it was in the books— the Henchperson has a few lines of dialogue that allude to them having an interest in interrogating traditional gender norms, and their disguises include more feminine roles while their undisguised look is noncommittal and their voice and figure are more masculine.
• Ascended Extra: The book version of the character is mostly silent, never says a word save for an occasional grunt or roar, and is the only one never in disguise, while this version has lines and actual characterization and takes over the Hook-Handed Man's role as "Nurse Lucafont" in The Reptile Room, and again takes it up in The Hostile Hospital. They're also Spared by the Adaptation so far, meaning a longer tenure on the team.
• Captain Obvious: When the troupe is admiring Captain Sham they say, "I'm talking to myself about Captain Sham."
• Cloudcuckoolander: The most absent-minded member of the group.
• The Ditz: They don't seem to know what the two white-faced women were talking about when they mention about strangers being nearby ("Strangers, where?"). They also don't seem to know math very well as shown during the auction when they try to bid 120 on VFD when the bid was 121 at that time.
• The Eeyore: The Henchperson isn't necessarily a downer, but their attention seems unfocused and largely disinterested in whatever's going on (excepting cases where they are more contrarian), making them the most downbeat and cheerless member of Olaf's troupe.
• Hidden Depths: Despite not being all there most of the time, there are moments when they voice opinions that are surprisingly insightful, such as their fair-minded thoughts on gender politics.
• Minion with an F in Evil: Easily Olaf's most incompetent and disinterested troupe member.
• Spared by the Adaptation: Makes it out of the burning Heimlich Hospital, and still alive at the end of Season 2. Lampshaded subtly by the fact that, when Olaf's troupe is driving away from the wreckage, they're the last to arrive, having kept the group waiting for some time. Instead, they abandon Olaf in Season 3.

Carmelita Spats

Carmelita Spats

Portrayed By: Kitana Turnbull

A spoiled girl obsessed with her own adorableness. At Prufrock Prepatory School she manages to go unpunished for her awful actions due to being the Vice Principal's favorite student. Later she willingly joins the villains when Esmé decides to adopt her.

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• Adaptational Attractiveness: Well, not attractiveness obviously but she isn't nearly as sour-looking as her book counterpart. She's also always clean and well-dressed, as opposed to her book counterpart who was described as unkempt.
• Adaptational Villainy: In the book, she was just a minor bully at first who only joined Count Olaf much later on. Here, she agrees to help Olaf in the same episode she's introduced in.
• Affably Evil: Except when she's in full Alpha Bitch mode towards the orphans she bullies, in which she is insufferably and transparently Faux Affably Evil.
• Alpha Bitch: She's at the top of the school's social ladder (points for also being a cheerleader), having gotten there by basically bullying everybody into submission.
• Ascended Extra: While she does have a major role in the Book 5 episodes as Prufrock Prep's resident bully, that's pretty much her only appearances in Season 2. Season 3 increase her role when she becomes a part of Olaf's troupe.
• Daddy's Little Villain: After joining Olaf's troupe, she is treated like Esmé and Olaf's adoptive daughter.
• Does This Remind You of Anything?: When she shows up at night in the cafeteria, she sniffs over the powdered sugar in a cake; the act itself seems like she's sniffing cocaine.
• Enfant Terrible: Often goes beyond spoiled brattiness and into outright sociopathy because it amuses her. Case in point: when asked to read To Kill a Mockingbird, she instead finds an actual mockingbird, kills it, and gleefully presents its body to the librarian in a box. It's also mentioned in a throwaway joke that Olaf and Esmé managed to keep Carmelita because her parents wouldn't pay a ransom to get her back!
• Foreshadowing: Duncan outright refers to Carmelita as the "cakesniffer" when he and Isadora defend the Baudelaires. Then, when Jacques calls her a "cakesniffer", she gets very insecure. It all comes down to a later scene where she sniffs the cake, and that's just putting it plainly.
• Hate Sink: An insufferable Alpha Bitch. While Olaf and Esmé are entertaining in their villainy, Carmelita is just grating. Even Olaf finds her unbearable.
• Hypocritical Humor: Carmelita calls the people she bullies "cake-sniffers," yet is later seen in the cafeteria plunging her nose in one and smelling it, even sniffing the powdered sugar in it like cocaine.
  Jacques: In my experience, it takes one, to know one... cake-sniffer.
• Irony:
  • She mocks the Baudelaires and the Quagmires for being orphans, and even Vice Principal Nero brags about her to Violet, Klaus, and Sunny for having two living parents. It's implied that her parents perished when the Man with the Beard but No Hair and the Woman with the Hair but No Beard burned down her house, and even being under the guardianship of Esme and Olaf doesn't last when the latter outright disowns her.
  • Her go-to insult is "cakesniffer." See Hypocritical Humor.
• Jerkass: Yes, spending most of her time mocking and insulting the Baudelaires and the Quagmires simply because they're orphans.
• Large Ham: Goes with the job description when you're the head cheerleader. She spends every second of screentime devouring the scenery.
• Light Is Not Good: In a scenario filled with dark, muted colors, she is a bright pink spot, but she's one of the biggest jerks around and makes every bad situation worse with her actions.
• Little Girls Kick Shins: In "Grim Grotto Part 1", Carmelita kicks Phil in the shin — which somehow still hurts him even though the shin she kicked was a metal prosthesis.
• No Celebrities Were Harmed: She is basically what would happen if Shirley Temple never went to Hollywood and was an out-and-out bitch.
• Pink Is Feminine: As above, instead of wearing the school uniform she wears an offensively pink and frilly dress.
• Spoiled Brat: Is treated like royalty by Vice Principal Nero and Esme, and is allowed to take whatever and go wherever she likes whether Prufrock, Mortmain Mountains, or under the care of Olaf (to which even he gets annoyed at it). It's amazing she learns anything.
• Uncertain Doom: Like several other characters, it is not revealed whether she survived the fire at Hotel Denouement. Although, considering she was last seen being tricked into heading to the laundry room (where the fire was started) by Olaf, her chances aren't good. If so, this might count as Death by Adaptation, as she was indicated to still be alive in Lemony Snicket: The Unauthorized Biography.

The Freaks

In General

The Freaks

The three freaks of the Freak Show from the Carnival. They are added as part of the troupe at the end of "The Carnivorous Carnival".

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• Adaptational Angst Upgrade: In the series version of "The Slippery Slope" they are harassed and unaccepted by the rest of Olaf's troupe which leads the freaks to regret their choice to join Olaf. In the book version of the "Slippery Slope", the white-faced women and Fernald treated them normally despite seeing them as freaks and seemed to fully accept them as their new colleagues, with the women mourning their white faces, and Fernald envying Kevin for actually having hands. The only one Olaf's henchpeople to be against working with freaks, the bald man, died before the freaks joined Olaf.
• Because You Were Nice to Me: Downplayed, the Count was never nice to them, but they were offered a place to be.
• Death by Adaptation: They end up unceremoniously killed by The Man with a Beard but No Hair and The Woman with Hair but No Beard in "The Slippery Slope" while in the books, they lived long enough to appear in "The Penultimate Peril".
• Face–Heel Turn: They seemed like nice people, but when the opportunity to leave showed up, they took it and turned against the Baudelaires, cutting the rope to the carriage Violet and Klaus were in to let them fall off the cliff.
• Heel–Face Door-Slam: They quickly have second thoughts about joining Olaf's troupe, and discuss the possibility of running away. Then they get suddenly murdered while they're alone.

Hugo the Hunchback

Hugo

Portrayed By: Kevin Cahoon

One of the three freaks who work at the carnival. He's rather excitable, and has a hump on his back that makes him stand out.

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• Adaptation Personality Change: He is mostly quiet and reserved in the books. In the series he is lively and childish.
• Hidden Depths: He is apparently in charge of carnival marketing and brand management, although seeing its decrepit state, his expertise wasn't nearly enough.
• Meaningful Name: Hugo refers to Victor Hugo, author of The Hunchback of Notre Dame.

Colette the Contortionist

Colette

Portrayed By: Bonnie Morgan

One of the three freaks who work at the carnival. Her draw to fame is her extreme flexibility, allowing her to contort herself into a variety of unnatural positions.

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• The Cast Showoff: Played by Bonnie Morgan, who's a real life contortionist. Most, if not all of what she does probably aren't special effects.
• Villainous Crush: During Count Olaf's "Freaks" song, he draws attention to Colette's freakish contortions, denouncing them as abnormal and disgusting, but the Hook Handed Man seems to find her contortions rather sexy, though Olaf cuts him off mid-sentence with the next verse.

Kevin the Ambidextrous

Kevin

Portrayed By: Robbie Amell

One of the three freaks who work at the carnival. Despite being completely normal otherwise, his "problem" is that he's ambidextrous, meaning that both of his hands are equally strong. He still sees himself as a freak, even when told that being ambidextrous is completely normal.

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• Adaptational Attractiveness: His looks were never mentioned in the book, but here he's quite handsome. It adds to the joke of him considering himself to be a hideous freak.
• Age Lift: He is described as wrinkly in the novel, but here he is played by a young actor.
• Even the Guys Want Him: In an aesthetic way; both Violet and Klaus comment on his "pleasant facial features".
• Cursed with Awesome: Most people (outside of this universe) would consider being ambidextrous to be both cool and useful, but Kevin thinks it makes him a hideous freak.
• The Eeyore: Even though he's probably the least freakish of the freaks, he still sees himself as horribly abnormal, and wishes he could just have a single dominant hand.

Others

Dr. Orwell

Dr. Georgina Orwell

Portrayed By: Catherine O'Hara

An optometrist in Paltryville who serves the workers of Lucky Smells Lumbermill.

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• Adaptation Dye-Job: Was blonde in the books but has dark hair in the show. Lampshaded twice; first when she is shown touching up her hair dye just before opening the door to Count Olaf, who comments, "You changed your hair;" and later when Klaus is being hypnotised, she mentions "bottle blonde" and a picture of her appears on the hypnotism screen... and she's entirely blonde.
• Ascended Extra: In the books she has no personal history with Olaf or the Baudelaire parents, just a one shot lackey who was promised a share of the Baudelaire fortune by Olaf. Here she was a former friend of the Baudelaire parents and Olaf's ex.
• Big Bad Duumvirate: With Olaf during The Miserable Mill where she acts as Olaf's partner rather than subordinate.
• Casting Gag: Her actress, Catherine O'Hara, previously played Justice Strauss in the 2004 film adaptation.
• Child Hater: Mocks the idea of primal maternal instincts.
• Contrasting Sequel Antagonist: While The Miserable Mill isn't technically a sequel she fits the role of being a much more intelligent, less hammy, and less humorous villain who's introduced after Olaf, and also has more of a personal grudge against the Baudelaires.
• Cruel and Unusual Death: Orwell accidentally backs into the lumbermill's furnace and is roasted alive.
• Dartboard of Hate: Orwell is introduced throwing darts at one with Olaf's photo. Hardly surprising, since he stole her valuables, left her to drown, and dumped her last time they saw each other.
• Dies Differently in Adaptation: In the books, she trips into the path of the mill's buzzsaw and is ripped apart, just as she tried to do with Charles. In the series, she stumbles backwards into the furnace and burns alive, a less karmic but less visibly-graphic death.
• Evil Genius: By far the most intelligent villain in the show and one of the smarter adults in general.
• Four Eyes, Zero Soul: She wears glasses and is highly evil.
• His Name Is...: At the end of "The Miserable Mill, Part II," her big speech about her motives and backstory is interrupted by her death.
  Dr. Orwell: You think you're so clever, but you only see in black and white. Just like your parents; they were shortsighted too. With their "You can't hypnotize people!" and, "What about free will?" and, "We're going to kick you out, and have your license revoked, and if we ever have children, we're never gonna let you anywhere near them!" Well I showed them! I'll show everyone! It was never about the fortune. It's about-ah!
• It's Personal: As you can see by her Motive Rant, the Baudelaire fortune is only part of the reason that she's gone after the trio, her main goal is revenge and the grudge she had against their parents.
• Large Ham: Mostly averted, but her hypnotism of Klaus has her hamming it up a bit.
  "TELL ME WHAT YOU SEE, KLAUS!"
• Like an Old Married Couple: With her ex-boyfriend, Count Olaf. They would be The Masochism Tango if their attraction wasn't overpowered by their mutual antagonism of each other.
• Mass Hypnosis: Her main service to the Lucky Smells Lumber Mill, but Sir is completely unaware of this, though it's not like he's bothered to ask.
• Meaningful Name: Her name is a reference to George Orwell, whose most famous work Nineteen Eighty-Four includes the suppression of free will and the erasure of history, themes that also appear in the episode.
• Morally Ambiguous Doctorate: She's apparently been barred from practising optometry due to her use of hypnosis. The Baudelaire parents were somehow involved in her license being revoked.
• Predecessor Villain: Acts as one to Season 2 Antagonist, Esmé Squalor; another old flame and willing accomplice of Count Olaf's.
• Revenge by Proxy: She wants the Baudelaires dead because their parents got her medical license revoked.
• Skewed Priorities: During her final rant, Dr. Orwell's biggest complain is not about the Baudelaire parents trying to stop her experimenting on people, but because they wouldn't let her near their children, since at that part she starts tearing up.
• Suspiciously Similar Substitute: The expansion of her character ends up making her very similar to Esmé Squalor; she has a romantic past with Count Olaf, she was entangled in VFD, and she bears a grudge against the Baudelaire parents that she's more than willing to transfer to their children. However, unlike Esmé, she's smart enough to realise that Olaf will screw her over and that Olaf is as dumb as two short planks and that she will have to do the work by fixing his mistakes.
• Suspiciously Specific Denial: During Season 2's flashback to the party at VFD headquarters, she immediately claims without prompting that she doesn't hypnotize men to get boyfriends; her companion at the time is acting fairly robotically, so it's not hard to figure out her guilt.
• Unholy Matrimony: Zigzagged with Count Olaf.
  Klaus: They're a wretched pair of villains, and they deserve each other.
• We Used to Be Friends: With the Baudelaire parents, as seen in Aunt Josephine's photographs before something happened that put her down a darker path to use her patients as unwillingly hypnosis subjects.
• Would Hurt a Child: Was quite prepared to throw Sunny into a furnace.
• Working with the Ex: With Olaf in "The Miserable Mill". It ends about as well as can be expected...

Ernest Denouement

Ernest Denouement

Portrayed By: Max Greenfield

One of the three triplets who manage the Hotel Denouement.

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• Affably Evil: Compared to his brother Frank, he is more personable and relaxed when speaking to the Baudelaires.
• Friendly Enemies: They might be on opposite sides of the Schism but Ernest still works with his brother Frank to manage the hotel. He is also visibly distraught by the death of his other brother Dewey, who is on the good side.
• Hero Killer: On Olaf's orders, he fatally dunks Larry Your-Waiter in a pot of boiling curry.
• Mathematician's Answer: When asked whether he’s Frank or Ernest, he replies either "Exactly" or "I am".
• Silent Snarker: Rolls his eyes a lot during the Baudelaire's trial whenever a positive case is made for them.
• Uncertain Doom: As with Frank, it is unknown whether he survived the fire that destroyed Hotel Denouement.

Ishmael

Ishmael

Portrayed By: Peter MacNicol

Ishmael is the facilitator of an islander cult who has a mysterious past in VFD.

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• Adaptational Heroism: Downplayed, but he is more protective and welcoming towards the Baudelaires and the show removes the instance of him taking an apple for himself while refusing to allow anyone else to have one.
• Final Boss: He is the final antagonist of the series, his threat surpassing Olaf's in The End who is reduced to nothing more than a pathetic, yet tragic figure who ran out of schemes to mess with the Baudelaires.
• Greater-Scope Villain: In the Netflix series, instead of being just a member of the V.F.D., he is the founder of the organization, making him responsible for all of the events in the series.
• Karma Houdini: Gets away with drugging the islanders with an amnesiac opiate. Though he may have perished at sea.
• Noble Demon: He is a cult leader who drugs the islanders to keep them under his control and tries to do the same to the Baudelaires, but genuinely cares about them and wants to protect them. He immediately realizes the threat Count Olaf poses and protects the Baudelaires from him. He is also the original founder of V.F.D. and an old friend of the Baudelaires' parents.
• Well-Intentioned Extremist: He keeps the people of the island from leaving the island using an opiate to make them forget their past lives because he believes it would be easier than having to endure the horrors of the world after witnessing the V.F.D. organization fall apart.