Spoilers for the entire series are unmarked.
The protagonist: An eccentric, gentle performer who since the late 1980s has emceed the children's television show Mr. Pickles' Puppet Time and become one of the most beloved people in the U.S., if not the world, with his lively antics and warm lessons of friendship, optimism, and kindness. He truly believes in these things and strives to embody them both on and offscreen...but it is far from easy. His marriage to Jill and especially raising his twin sons Phil and Will often was affected by his commitments to the public, and then a year before this story begins, he loses Phil in a terrible freak accident. Now estranged from his wife and surviving son, and unable to properly process his grief and rage — thanks to his father and executive producer Seb's obsession with maintaining the Cash-Cow Franchise the show has become — he is undergoing a Sanity Slippage that risks everything he holds dear. As his mind and heart bottom out, he must confront and atone for the darkest parts of himself, understand what led him to this point, and figure out how to emerge from it for the sake of, if no one else, the children who love him. He comes to realize that his puppet analogue in Mr. Pickles' Puppet Time is The Oops, a loose-limbed, clumsy monster prone to making mistakes.
- Adult Child: He lives in a box of innocence both on and off set, in part because Seb's encouraged and enforced it.
- All-Loving Hero: His defining trope via Decon-Recon Switch. His desire to be loving to everyone — even those who hurt him — and responsibility to keeping up the image of "Mr. Pickles" in public start eating him alive over the course of Season One, as he struggles to express his anger, pain, and guilt in ways that won't hurt others. At the end of the season, he both gets his show cancelled with his heartbreaking speech at the tree lighting ceremony and hits Peter with his car on Christmas Eve. Season Two is his Redemption Quest as he struggles to make amends and reconstruct this trope.
- Amazingly Embarrassing Parents: Played for Drama: Phil came to see him as this simply for being Mr. Pickles. Coming on top of Jeff's general struggle to interact with him constructively, as he tended to treat him and Will as he would his viewers, there was a definite rift between the two before Phil died.
- Catchphrase:
- On Mr. Pickles' Puppet Time, "See you at the bottom!" for the transitional segment that takes him from his house down to Picklebarrel Falls.
- In the final episode of Season One he introduces a new catchphrase — "I am listening" — that extends into Season Two.
- In Season One, in his offscreen life he often advises others "Don't use a bad word when you can use a good word." Early in Season Two, his amending this to "Don't use a bad word unless a good one won't do" is a signpost of his Character Development.
- Dark and Troubled Past: Over the course of multiple flashbacks throughout the series, Jeff's unhappy childhood is detailed: He did not take his mother's abandonment of the family well, and tried to follow her to Niagara Falls only to be stopped by his father, whom he shot in the face (harmlessly, but still) with a pellet gun. Unable to fight his father without the possibility of him fighting back, Jeff further developed the fantasy world of Picklebarrel Falls as a means of comforting himself and his sister. While he did try peewee hockey with Seb's encouragement, he discovered a capacity for physical rage that frightened him too much to continue. Instead, he chose the path of an All-Loving Hero by the time he was in college, where he realized his life's calling was to use television to connect with children and inspire them to be their best selves.
- Darkest Hour: His breaking down and hitting Peter with his car, and having to undergo risky surgery to save his life, ends up being this for him. Even as he experiences more disappointments and traumas in Season Two, he is growing a spine and handling his problems in healthier, though sometimes eccentric, ways.
- Dark Secret: He has but one he is loath to admit even to himself: He blames Jill for the accident that killed Phil.
- Depraved Kids' Show Host: Zig-zagged. Contrary to rumors, he was never a military sniper or anything like that (this parodies urban legends about Fred Rogers), and in fact is a truly All-Loving Hero who is terrified at his own repressed anger and potential for violence. BUT his mental breakdown over the course of Season One does involve him killing a parrot when he takes offense at its vile language...but he secretly replaces it and tries to give the corpse a proper burial in private...then at his lowest point, a moment of weakness, he hits Peter with his car and doesn't immediately admit it's his fault to Jill and Will...but he does feel so much guilt that when he realizes only he can save his life by donating part of his liver, he does and and comes clean to his loved ones...and in the penultimate episode he does beat a man to a bloody pulp in full view of a busload of kids...but it was to save Will's life and kids everywhere actually love him more for what he did.
- Expy: Subverted. The character, particularly his on-screen persona, is a mix of Fred Rogers and many other children's show hosts and creatives including Jim Henson and The Wiggles. There are even touches of Andy Kaufman, who like Jeff hosted a children's TV program in college and later applied the tropes of that work to some of his adult-oriented performance art. (Carrey played Kaufman in Man on the Moon.)
- Foot-Dragging Divorcee: He really wants to reconcile with Jill. Unfortunately, his nearly killing Peter results in her insisting that the divorce be finalized, and it is in "Episode 3101" of Mr. Pickles' Puppet Time — working the actual signing of the papers into the story because poor Jeff can't bring himself to be absolutely alone when he does it, and having no friends in his immediate circle, must turn to his sister and the puppets.
- Good Is Not Soft: He finally reconciles the anger in his heart with his All-Loving Hero nature when he embraces this trope to save Will from the stalker by beating the latter to a bloody pulp.
- Honesty Is the Best Policy: He has a hard time bringing himself to lie about anything, and if he does it doesn't last long — even regarding the circumstances of his hitting Peter with his car. The only reason the rest of the world doesn't find out what he did is that his family and Peter conceal what they know. His Dark Secret ends up being the one thing he has managed to conceal at length (see above).
- I Want My Beloved to Be Happy: Jeff truly loves Jill and Will and has a hard time accepting Peter's place in their lives to the point of attempting to kill him in a moment of weakness, but in Season Two, he concedes that Peter is a better match for her, is shocked that she doesn't accept his marriage proposal right away, and doesn't try to use her hesitation to woo her back.
- Jumped at the Call: In college, he witnessed the televised tragedy of the Challenger space shuttle explosion. Knowing that millions of children were watching along with him, he was heartbroken to realize that their dreams were crushed by the disaster...but inspired to find a way to use television to restore those dreams and make the world a better place, hence the creation of Mr. Pickles' Puppet Time, with its first original character (as opposed to those he'd come up with as a child) being Astro-Otter.
- Manchild: A saner but sadder version of this trope. He has adult intelligence and libido, and knows the real world is a much grimmer place than Picklebarrel Falls, but he has a perhaps too-idealistic view of his power to shape it for the better, tends not to indulge in other grown-up vices, and has the odd quirky habit such as drinking chocolate syrup straight from the bottle.
- My Greatest Failure: Although he secretly blames Jill for Phil's death (because she was the one driving the van and did not insist the boy wear his seatbelt; Jeff was not present at all), he also feels his death was a failure on his part because he didn't do more to listen to him rather than just talk to him when problems arose. Rethinking his life's mission in the wake of this, he decides he must do more to listen to his young viewers going forward.
- Nice Guy: He is a well-meaning adult who truly, truly cares about everyone — the kids who watch his show especially. Even when he's at his worst, he will do anything to make up for his mistakes. It's even suggested in "Up, Down and Everything in Between" that Peter becomes a bit nicer upon receiving part of Jeff's liver when the latter donates it to make amends for being the reason the former needed a transplant in the first place!
- Once Done, Never Forgotten: Jill will never let him forget he almost killed Peter on Christmas Eve, as it comes up in almost every confrontation they have in Season Two. He is frustrated by this.
- Outliving One's Offspring: It was far from perfect offscreen all along, but the death of Phil is the catalyst for his life crumbling apart.
- Papa Wolf: In "The Nightingale Pledge", he brutally beats up the stalker threatening Will, an incident that is witnessed by a whole school bus' worth of kids. This makes him both a public hero and even more popular with his young fans, even though it contradicts his usual Nice Guy nature.
- Sanity Slippage: Most of the first season consists of Jeff slipping further and further while no one around him seems to notice, or if they do, they either don't care or have their hands tied so that they can't offer him the help he needs. He bottoms out in the Season One finale as he has a public breakdown at the National Tree Lighting Ceremony and later hits Peter with his car in a moment of rage, and from there embarks on a Redemption Quest to rebuild his broken world.
- Stalker with a Crush: Downplayed and justified. His love for his estranged wife and son is so strong that even though he sees them regularly, he decides to buy the vacant house next door to theirs to secretly watch them from quasi-afar. However, he never fully moves into the house, though he leaves a bunch of suits and some food behind. It still causes a problem when Will and Peter find out what he did on Christmas Eve (during a teen stoner party in the supposedly vacant house), leading to a confrontation between Peter and Jeff that leads to the latter hitting him with his car.
- Trauma Conga Line: Poor Jeff just can't catch a break in Season One! He has a lot of setbacks in Season Two as well, but not to the extent of the first season.
- Wide-Eyed Idealist: Jeff knows that the world is a grim, cruel place especially for children, but he sincerely believes it can be better and his life's work is to make it so via Mr. Pickles' Puppet Time. While his idealism is tested again and again, and he must come to accept shades of gray in his life, he manages to earn a happy ending for his struggles.
The executive producer of Mr. Pickles' Puppet Time and Jeff's father. After his marriage fell apart in The '70s and his manic-depressive wife abandoned the family, he helped defuse young Jeff's pain and rage — and brought some control over everyone's lives — by encouraging his creativity, which manifested as the fantasy world of Picklebarrel Falls. As the decades have passed he turned his son's show into a massive Cash-Cow Franchise, but maintaining this has come at the expense of Jeff's sanity, as Seb micromanages both the show and his son's life — even in the wake of Phil's death leaving "Mr. Pickles" struggling to find an outlet for his pain. He is the inspiration for the gigantic Hopskotch the Sasquatch in Mr. Pickles' Puppet Time, who is only seen as a giant pair of legs and feet and occasionally a hand that can return Mr. Pickles from Picklebarrel Falls to the real world.
- Abusive Parents: Of the neglectful variety. Whether Seb realizes it or not, he does Jeff a massive disservice by ignoring his trauma and pain and forcing him to bottle it up for the sake of the show. Of course, this goes further back to the divorce; Seb was extremely controlling of the kids' lives and made it clear he would fight back if Jeff tried to confront him physically (as happened when the boy shot him harmlessly in the face with a pellet gun), and found that encouraging Jeff's creativity and the fantasy of Picklebarrel Falls was a way to keep things on a seemingly even keel.
- Control Freak: He micromanages Mr. Pickles' Puppet Time from its production to its merchandising, and is trying to do the same with Jeff's personal life as well. He takes some cruel satisfaction in watching Jeff and Didi try to take the show forward without him in Season Two, but then Laser-Guided Karma comes calling...
- Horrible Hollywood: He's not a terrible person but he cares far more about maintaining the franchise of Mr. Pickles' Puppet Time than Jeff's mental health. His primary response to Jeff's impending mental breakdown is to look into ways to remove Jeff from the show altogether, such as by launching an Animated Adaptation featuring a soundalike as Mr. Pickles. He's effectively rudderless in life once Jeff fires him, although he does get some satisfaction from seeing Deirdre and Jeff struggle with reviving the show.
- Laser-Guided Karma: After decades of ensuring Jeff and his fantasy world were under his control, he suffers stroke-induced dementia, trapping him in straight-up delusions. That he may be taken care of, Jeff checks him into an assisted living facility that recreates The '60s in a Fake Town, meaning he will live out his life in a different kind of fantasy.
Jeff's estranged wife, a nurse; they met at the Turn of the Millennium. Jeff was hesitant to pursue a relationship with anyone, knowing his responsibilities to the show could get in the way of lasting happiness, but he finally decided to reciprocate her love for him and for a decade or so they were blissfully happy. As the boys grew and Phil began to rebel, she became increasingly frustrated by Jeff's struggle to give them and her the love and understanding they needed, but there was still hope — until the terrible day the van she was driving the boys in was struck by a snack cake deliveryman's truck in a freak accident, killing Phil. With Jeff unable to process his grief thanks to the prison Seb has boxed him into, they are estranged and she is dating another man as she raises Will alone. She was the inspiration for the Mr. Pickles' Puppet Time character Thump Thump — Jeff Pickles' own anthropomorphized heart.
- Amicable Exes: With Jeff more or less as the series begins, less so as it progresses, leading to their divorce being finalized midway through Season Two. By the end their relationship is healed enough that Maybe Ever After is at play — she has not accepted Peter's proposal of marriage, but she hasn't rejected it either.
- Dark Secret: She donated Phil's organs anonymously after his death, and never told Jeff about it because she didn't want him bringing the people who were helped by it into his life and take away attention from her and Will (whom she lies to about it).
- Foolish Husband, Responsible Wife: How she sees her and Jeff's marriage and aftermath, feeling he is all too generous to others compared to her and her sons — in particular, she's horrified that he's paying the medical bills of the driver of the truck involved in the accident that killed Phil — and his idealistic ideas such as the interactive Mr. Pickles doll often go awry in ways that even inadvertently threaten them with harm. While she has a point with the latter, regarding the former it's clear she can't understand the mindset of an All-Loving Hero (Jeff knows that the poor man meant no harm, has a family to support, and is a public pariah because he "murdered" the son of Mr. Pickles).
- It's All My Fault: She blames herself for Phil's death because she was driving the van and hadn't insisted on the boy wearing his seatbelt. The climactic moment of her and Jeff's relationship onscreen is his admitting that he thinks it's her fault too, which is something she wants to hear.
- Love Cannot Overcome: Beyond the pain of Phil's death, she resents how Jeff's fame and altruism gets in the way of their personal relationship, leading to their estrangement. It only gets worse first when Jeff hits Peter with his car at the bottom of the former's Sanity Slippage, and later when a stalker almost burns down her house to get at Jeff. But at the end of the series, after some major revelations, Maybe Ever After is in play.
- Parent with New Paramour: As the series begins she is already in a healthy relationship with Peter, whom she met on the job.
- Taking the Kids: Ever since the estrangement Will has been living with her, and once the divorce is finalized, it's strongly implied she will have full custody.
One of Jeff's adolescent twin sons, and the survivor of the car accident, Will is struggling with survivor's guilt and his parents' estrangement. He's falling in with a "bad" crowd of stoners at school, and rejecting Jeff's attempts to reach out to him due to his increasingly cynical nature. But as he comes to explore his brother's past, he finds unexpected, even mystical, reasons to hope for better things. In tandem with Phil, they inspired the Mr. Pickles' Puppet Time characters PB & J, anthropomorphic sandwiches.
- Darkest Hour: He hits this in "The Death of Fil" during his "field trip" with Jeff to the burial at sea of the Filipino Mr. Pickles, when he learns that Peter is going to propose to Jill back home. He has a hope spot when he sees what appears to be the third number in the numerology sequence on a dinghy outside the ship, but when it proves wrong, he loses hope that the magic that can turn back time will work — and cruelly accuses Jeff of "killing the magic" by not working harder to get back together with Jill. Later, as the international Mr. and Ms. Pickles turn in their ties, he turns in the one Jeff just gave him. However, things turn around in "A Seat on the Rocket" when the third number appears after all as a result of Jeff switching house numbers to save the family from his stalker.
- First Father Wins: Played with: He realizes he loves Jeff more than Peter as the series progresses and wants things to return to how they were before Phil died, but Jeff's unwillingness to fight to restore his relationship with Jill makes Will resentful of him, the boy even calling him out as a wimp. When Jeff saves Will by beating up the stalker, Will realizes that isn't true even if his parents never do reunite.
- Pint-Sized Kid: Will is a freshman in high school (about 14), but he's quite short compared to other kids in school, and clearly hasn't quite hit puberty yet. Cole Allen was 12 during filming, slightly younger than Will.
- Significant Haircut: In "The Nightingale Pledge", he decides to have his long hair (which he kept that way mostly because Phil had the same cut) cut short, following on from his father's invoking this trope earlier in Season Two.
- Used to Be a Sweet Kid: It's shown that prior to Phil's death Will was a sweet, caring, almost model child, and his acting out is heavily implied to be due to unresolved grief. After a brush with disaster, however, he slowly regains his old nature as he explores the surprising legacy of his brother.
Phil was the other twin son of Jeff and Jill, who perished in the car accident. In life, he was embarrassed to be the son of "Mr. Pickles", and frustrated that Jeff's relationship with him was not all that different from Mr. Pickles' relationship with his viewers: being talked to thank listened to. As a result he became aggressive and cynical, much to his father's frustration — and any hopes of healing the rift perished with him.
- Creepy Child: More aggressive than outright creepy, but he apparently had a hobby of cataloguing the nation's murders (claiming it helped him learn spreadsheets), much to his parents' chagrin.
- Death of a Child: His death, shown in flashback in the first episode, is a major factor in Jeff being estranged from Jill and brings to light Jeff's inability to cope with his grief because he has no outlets to do so.
- Middle School Is Miserable: During the flashback episode "Philliam", set approximately a year before his death, Phil gets into a physical fight with a bigger kid over the latter calling Jeff a "psychic pedophile".
- Posthumous Character: The series opens on the one year anniversary of his death, which was the catalyst for both Jeff and Jill's separation and Jeff's mental health taking a sharp downturn, though both had been brewing beneath the surface for quite some time as shown in later episodes.
Jeff's older sister. Ever since he helped her cope with the divorce of their parents by creating the world of Picklebarrel Falls as children, she has been heavily supportive of him and his dreams, becoming the head puppet maker of Mr. Pickles' Puppet Time. But she has her own family and problems to deal with as Jeff's life begins to implode, and she may not be strong enough to overcome them and help him...yet. Her Puppet Time analogue is Astro-Otter, the first character Jeff created specifically for the show. She also appears as the character "D.I.Y. Didi" in "Episode 3101" of the Show Within a Show.
- Big Sister Instinct: The elder of the Piccirillo siblings and very close to and protective of Jeff, to the point that she initially refuses to make a mascot version of Jeff's head for the ice show until Seb bullies her into it, stating that she couldn't hurt him like that. She apologizes profusely when he catches her building it. It's not surprising that Jeff taps her to replace Seb as the Puppet Time showrunner after he fires the latter, despite her inexperience. Indeed, that and her protectiveness of Jeff becomes a problem when she allows too many of his ideas to go forward without thinking them through.
- Dark Secret: The school for girls in Belize that she's been financing for years? It's a front for embezzling money and stashing it offshore, tax free. When Scott finds out about this, she frantically works to cover her tracks by actually donating a great sum to charity.
- The Unfavorite: She is this to Seb. Because she handled her parents' divorce more healthily than Jeff did, Seb turned to encouraging Jeff's imaginative side as a way of bringing order to the broken household, and eventually focused on exploiting him and his creations as an adult. And because she works behind the scenes rather than in front of them, her contributions to the show are marginalized.
Deirdre and Scott's only child and Jeff's niece, she's a...strange child who only grows stranger in the wake of her parents' impending divorce.
- Companion Cube: In "The Cleanest Liver in Columbus, Ohio" she receives an ax as an impromptu additional Christmas present. She loves it and names it Delores!
- Creepy Child: She turns out to have been keeping her baby teeth to use as part of a hand puppet of her own that inevitably freaks everyone who sees it out, periodically screams for no apparent reason early on after her parents' marriage starts falling apart, adopts an ax as a Companion Cube, and so on and so forth.
