Prince Charmless

Looks like a stallion, acts like a foal.

"I was raised to be charming, not sincere."

— Cinderella's Prince, Into the Woods

The opposite of Prince Charming, a prince, or someone at least of high nobility, who is absolutely wrong for the heroine or Love Interest, because he is boring, shallow, or a total jerk (if not outright The Evil Prince). The princess will either fall for that prince at first or have an Arranged Marriage with him, but she will end up with the commoner guy instead (who might be a prince himself and not know it). This is a common character in Fractured Fairy Tales.

Despite the title, this can happen with princesses. It's just rarer.

A variation on the Romantic False Lead — except here the "prince" is clearly the Wrong Guy. This may be done to Prince Charming retroactively by Derailing Love Interests.

Not to be confused with Prince Charming Wannabe, who is not a literal prince, but often displays many of the same wrong-guy traits as this guy.

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Examples:

Anime & Manga

• Berserk: Griffith zigzags this trope a lot, as he behaves like a stereotypical Prince Charming to Princess Charlotte, but he is only using her to rule the Kingdom of Midland. However, he is capable of hiding his dark side so well that NO ONE thinks that he's charmless or even evil in the slightest sense, even some readers can be fooled. However, once the Eclipse goes down, Griffith shows us that he's not just Charmless... he's pure evil. (he still is pretty charismatic for the Kingdom of Midland, as he finally managed to succeed in his goal to become a ruler, and the Pope of Berserkverse has declared him the Big Good and The Chosen One.)
• Code Geass: First Prince Odysseus U Britannia (a nice guy compared to the rest of his mostly ruthless, brutal, egotistical, bellicose, bloodthirsty, cunning, sadistic, sociopathic, racist, megalomaniacal, 31 flavors of balls-to-the-wall batshit insane, and downright assholish kin but not very bright for the heir apparent to Britannian throne) almost has an Arranged Marriage with Token Mini-Moe Tian-Zi, the Empress of China. Obviously, it was not meant to be.
• Hotohori from Fushigi Yuugi has some shades of this trope, mainly because he hasn't learned to interact informally with people due to his sheltered existence, and also because he's more than a little vain. He's actually very nice, and he means well, though.
• Kagerou of Inu × Boku SS. He's not a literal prince, but he is the heir to a wealthy and influential family and is the arranged fiancé of the main heroine. His outrageous behavior completely betrays any prestigious upbringing you'd expect him to have and does nothing to endear himself in his fiancée's eyes. He is extremely hammy and rude, has an incessant need to create a Big Entrance for himself, and compulsively categorizes literally everything he sees into being either a Sadist or a Masochist.
• Mildly downplayed with the Emperor from The Tale of the Princess Kaguya who, though he carries himself with grace, is also an egocentric twit who arrives at the conclusion that Kaguya must've refused all other suitors because she's waiting for him to propose. After this, he goes on to decide that he's Entitled to Have Her and attempts to take her with him against her will, reasoning that no girl has ever wanted him not to take them. Even after Kaguya has made it as clear as possible that she wants nothing to do with him, he insists that it's his conviction that her happiness is dependent on her belonging to him... Unbeknownst to the Emperor, it was his actions, and the severe emotional effect they had on Kaguya, that triggered the Emissaries from the Moon to come to Earth in order to take Kaguya away with them.
• Wolfram from Kyo Kara Maoh!. He's a Royal Brat, and also constantly accusing his fiancé of cheating on him, and berating his fiancé.
• Mobile Suit Gundam SEED Destiny: Yuna Roma Seiran. Foppish, tactless, and supremely arrogant, Yuna was so unlikeable that fans actually wished Cagalli had just shot him on the spot during their first meeting. Super Robot Wars K tries to moderate this somewhat, with some limited success.
• One Piece:
  • Wapol was a disgusting prick long before he became a tyrannical king, to the point that even his own father was worried about him and laments spoiling him at a young age.
  • World Noble Charlos is even worse than Wapol as he routinely abuses commoners, buys women for sexual slavery, and is fantastically racist to Fishmen. However, this attitude only gets him slugged and brained in on two seperate occassions.
  • Sterry is a loathsome Royal Brat who bullies his White Sheep brother Sabo, and becomes even worse when he becomes king after the previous king died under "suspicious circumstances".
  • Most male Nobles are like this, as seen by the unabashed Sadist Doflamingo, whose behavior nearly got his whole family executed; and the Gonk Noble boys who tried to marry Princess Shirahoshi and were shocked when she stated they "weren't her type".
  • Cavendish (who is revealed to be an actual prince) is treated as a Prince Charming by women, but is actually a massive insufferable Attention Whore who gets pissy and violent to anyone who's more popular than him. He does mellow out somewhat when the Straw Hats save from being turned into a toy (he even helps them against the Donquixote Family and then becomes the representative of the first Division^note his crew, the Beautiful Pirates of the Straw Hat Grand Fleet), though he's still narcissistic.
  • Princes Ichiji, Niji, and Yonji are certainly charmless especially compared to their brother Sanji as they treat underlings like dirt, waste food, and violently abuse female servants. Even Nami, who has a Money Fetish, was disgusted at Yonji being attracted to her;, and later on, Niji pervertedly talks about how he wants to negotiate with Big Mom to give Nami to him. The reason they're like this is that their father Judge removed their humanity during birth.
• The noble title of Conrad in Rune Soldier Louie isn't entirely clear, but he has all the traits of the trope. He's even worse at being a hero than Louie, who at least has the spirit to help people and shows some degree of competence, while Conrad is just an Upper-Class Twit.
• Zig-zagged in Slayers. Lina Inverse is seeking out to meet Crown Prince Philionell of Saillune, thinking he's the typical Prince Charming, to charm him into marrying her. When she encountered him, she found out that he's a boorish man more fit to be a bandit chief, and old enough to have a daughter not much younger than Lina. But it turns out Phil is a nice guy after all; Lina's matrimonial plans shatter, but she still befriends Philionell. Phil's daughter, Princess Amelia, even becomes a permanent member of Lina's adventuring party.
• Prince Raji Shenazard of Snow White with the Red Hair is a Royal Brat with a reputation for frequenting the Red Light District, and whose status as a Upper-Class Twit has led to him being referred to as "That Stupid Prince" or "Idiot Raji". He first appears when he has his kingdom searched for its most beautiful woman to become his concubine. When the title character is brought to his attention due to her rare and striking hair color, he tries to have her poisoned and brought to him even after she flees the country to escape him and presents her with a Scarpia Ultimatum when Zen is poisoned instead. His entitled mindset also keeps him from realizing that she doesn't actually want anything to do with him.
• Kirakira Precure A La Mode has Prince Nata, of the sweets-loving Kingdom of Confetto, attempting to woo Yukari to be his princess. When Akira protests, he challenges her to a series of competitions where he proceeds to cheat and make a fool out of himself trying to best Akira. When Yukari ultimately declines his invitation, he does gracefully accept her desires and wishes the best for her and Akira.
• Mobile Suit Gundam: All of the Zabi brothers (yes, even Garma, particularly in Gundam: The Origin), but especially Gihren, who is hell-bent on taking over the world. His father even invokes Godwin's Law on him.

Comic Books

• Fables: Prince Charming is this to Snow White. And Sleeping Beauty. And Cinderella. And almost Beauty. Yeah, he gets around. Eventually, he does turn his life around and is killed saving the world. To help clarify, he has a natural ability that makes people instinctively like him, but after a time it no longer has an effect; by the time he first appears in the story, he's managed to charm his way into and subsequently get chased out of every royal and noble house in Europe.
• Avatar: The Last Airbender - The Search shows before that becoming Fire Lord, Ozai is this to Ursa. Ursa does not love him, as Ozai is a manipulative, power-hungry jerk, but she is forced to marry him. Instead, Ursa has already fallen for a commoner named Ikem.
• Briar: Prince Rodion was a hero who was supposed to wake up Briar in order for them to marry and rule both their kingdoms. Unfortunately, Rodion was much more into the idea of marrying Briar without waking her up and becoming a conqueror with her father.

Fan Works

• Ever since he became heir to the chiefdom, Snotlout in Prodigal Son has only gotten worse, flaunting his position in different, equally obnoxious ways, one time being him having Tuffnut announce his presence to everyone at the Great Hall while riding a horse surrounded by a harem of sycophantic girls.
• In Lost in Camelot, Sir Leon is clearly regarded as a low-key example of this when Uther reveals that he intends to force Bo to marry Sir Leon. Bo and Morgana recognise that Leon has many good qualities, but his dedication to the rules makes him a poor fit for Bo's more rebellious nature, and on a practical level Bo would never be able to sustain her need for chi by feeding on a single normal human.

Films — Animated

• In Alpha and Omega, Garth is the son of the Eastern Pack's chief, and is arranged to marry the daughter of the Western Pack's chief for the two packs to be united. Garth is rather unintelligent and boastful, and she is completely unimpressed, eventually falling in love with a commoner. Subverted in that Garth isn't evil, and does still want the best for both packs. He also eventually finds love.
• Happily N'Ever After: The prince. No wonder Cinderella married a commoner. Subverted in that he is actually happy for the couple. He even pays for their entire wedding.
• In Shrek 2, Prince Charming is supposed to marry Fiona, but his personality does not endear him to her. He doesn't see why she doesn't love him, so his mother the Fairy Godmother resorts to drugging her with a love potion, only to be stopped by Fiona's father King Harold's refusal.
• Disney:
  • Beauty and the Beast: The Beast started out this way and is largely the reason why the Enchantress cursed him. Gaston is also meant to be a deconstruction of the typical Disney prince, though he doesn’t count for this trope specifically as he is not of any royal family.
  • Aladdin: In his first appartion, Prince Achmed tries to whip two children because they ran in front of his horse and pushes Aladdin into the mud when the hero defends them. Later, he is described by Jasmine as "overdressed and self-absorbed", and her pet tiger Rajah doesn't seem to like him very much either. We don't get to see his behavior toward the princess specifically, however, just him walking indignantly away, having lost the seat of his pants to Rajah.
  • The Princess and the Frog: Prince Naveen is a handsome prince whose charm causes all the ladies to swoon over him. Tiana, who has to spend the majority of the film with him after they were cursed to be frogs, sees right through his façade, as she immediately discovers he's a Spoiled Brat who expects her to do everything and is only interested in marrying her best friend, the daughter of a wealthy business owner, because his parents got tired of his mooching and cut him off from their money. He gets better though.
  • Frozen: Prince Hans initially averts this by appearing to be a noble gentleman like the usual Prince Charming, but later plays it straight when he is revealed to be a conniving, manipulative sociopath. To be fair, unlike most examples of this trope, he DOES have charm. Just not the good kind.
• Red Shoes and the Seven Dwarfs features the obnoxious Prince Average (whose name he insists is pronounced "Ah-voo-RAHJ") as a secondary antagonist.
• The Secret of Anastasia: Prince Paul invokes the phrase verbatim for his Villain Song. Taken a bit further than most examples. He's not a prince at all — he's actually the ruthless Secret Policeman Checka, who murdered the real Prince Paul and is posing as him to romance Anastasia, steal the Romanov fortune, and dispose of her.

Films — Live-Action

• Prince Valium from Spaceballs. This is a mild case since he's too sleepy to show any obnoxious personality traits or any actual personality. He's just so boring he apparently even bores himself.
• Prince Leopold from the The Illusionist (2006) is a domestic abuser and has a terrible temper when he doesn't get what he wants.
• Chad from Descendants is the son of Cinderella and her prince, and clearly did not inherit their better traits. Before manipulating Evie into doing his homework for him, he strung along around a dozen other girls at the same time for similar purposes. He may be an invoked example of this trope, created to show that the VKs were far from irredeemable just because their parents were villains.
• Commodore Norrington in Disney's Pirates of the Caribbean: The Curse of the Black Pearl is a broad subversion of this trope, which is very common straight in the studio's animated library. While he is an antagonist to the pirates and Elizabeth Swan does not connect with him, he is genuinely respectful of her in a stilted gentleman, period romance way and otherwise has strong positive traits.
• Downplayed in Maleficent where the only thing wrong with Phillip is that his kiss turns out not to be enough to wake Aurora. The pair do end up getting married in Maleficent: Mistress of Evil.

Literature

• In By The Sword by Greg Costikyan, the princess has great misgivings about her Arranged Marriage to one of these princes. The prince is fat, smelly, and has bad table manners. The princess eventually talks to a member of the prince's court, who explains that the prince is actually a very gentle man, and he's also extremely gay, so the princess never has to worry about having to have sex with him. She is reassured by this and decides that this marriage won't be so bad.
• The Chronicles of Prydain:
  • Prince Ellidyr is not at any point set up to be the heroine's love interest but otherwise fits the trope perfectly. And given that the heroine is a princess while the hero is a commoner, it's not a reach to understand why the hero was a little nervous about the possibility of such a match arising anyway.
  • Prince Rhun was at first this trope played straight. Although not malicious, he was a bumbling klutz and The Millstone to any group saddled with him. There was talk of betrothing Eilonwy to him in the future, and Taran was disgusted and furious at the thought. He was never as stupid as Taran initially thought, however, nor was he ever malicious, and he did do some growing up.
• Discworld: The Duc in the novel Witches Abroad. He's not technically a prince but the principle applies. He's in cahoots with evil fairy godmother Lilith, and Magrat is called in (with Granny Weatherwax and Nanny Ogg along for the ride) to save Emberella from marrying him. And he's a frog; Lilith enchanted him into a prince.
• Prince Ghyaneth of Berringey in Elemental Blessings. He's blunt, rude, Berrincentric, and his country practices routine regicide of every royal save the heir to ensure there are no factions or coups. Princess Josetta can't stand him.
• Therandil in the Enchanted Forest Chronicles (on purpose, since it's a Deconstructive Parody). Most of the princes in the series are like this. It's implied that most of them mean well, though, and—like princesses—were just given "traditional" upbringings which resulted in their silly behavior.
  • This is extra-fun because Therandil actually does fit most of the qualifications for a straight-up Prince Charming: he's handsome, brave, honest and well-meaning, a skilled fighter, and does his best to Always Save the Girl. The problem is, he's also dumb as a brick and doesn't quite get that Cimorene prefers serving a dragon to living in a castle.
• In the Heralds of Valdemar series:
  • Young Queen Selenay is swept off her feet by one of these, only to realize too late what a mistake she made. The Heralds keep silent rather than let her know that they have misgivings about the match since they don't have any proof to back things up, and outright trying to forbid the marriage would just make her more insistent on the marriage, and it nearly backfires fatally when the Prince and his friends try to assassinate Selenay.
  • His brother, Prince Darren, starts off as one of these but eventually learns sense.
  • Prince Ancar of Hardorn, who attempts to marry Selenay's daughter, is one of these at best: then he throws off the mask and shows what a monster he actually is.
• Not a prince, per se, but Captain Phoebus from The Hunchback of Notre Dame is of noble birth and presents himself as a Knight in Shining Armor to Esméralda, but his true personality is that of a Jerkass and he never really loved Esméralda - to the point where he lets her hang for murder while knowing she's innocent, and that all it would cost to save her would be a minute or so of his time - since she was accused of killing him, simply stepping forward to point out that he wasn't dead would be all that he needed to do to stop the execution.
• The Mermaid's Daughter: Fand, also known as The Little Mermaid, fell in love with a cruel prince who became sexually obsessed with her and planned to keep her on as a concubine. After Fand left him and went inland (instead of turning into a daughter of air as in the original story), he spent the next twenty years mistreating his wife and the people in his court. When she finally returned, planning to stab him so she and her daughter could turn into mermaids instead of living painful lives on land, the prince's first act was to try to rape her. Even then, she couldn't bring herself to kill him.
• Played with in The Paper Bag Princess; Prince Ronald is clearly this, and Princess Elizabeth realizes this at the end, but there's no lower-class equivalent for him. So she dumps him and lives life alone—played as a Happy Ending.
• In Prince Charming, Princess Anastasia is afraid her young brother, Dmitriv, might actually be this for Vasilisa. Lazy, irresponsible, and a flirt, Dmitriv doesn’t look like the best match for the good-hearted Vasilisa. Subverted in that Dmitriv resolves to make a change for the better by the end.
• The Prince in Roald Dahl's Revolting Rhymes is downright Axe-Crazy, cheerfully chopping the heads off the ugly sisters so he doesn't have to marry them. Cinderella is horrified and marries a jam-maker instead.
• In The Royal Diaries: Catherine: The Great Journey by the time Catherine married the weak Manchild Peter III Of Russia, he was disfigured and once he ascended the throne, his loyalty to his country of birth ruined Russia's successes in the Seven Years' War.
• A Song of Ice and Fire
  • At first, idealistic young Sansa Stark believes Joffrey to be a Prince Charming and is greatly looking forward to their arranged marriage — but after things go to hell and she becomes a prisoner of war at King's Landing, she quickly realizes Joffrey is not just this trope when he doesn't have to mind his manners in public, but he is a totally spoiled sadist on top. She realises her life with him will be far from happy. She still has to keep up the façade of loving him, however, lest her time at King's Landing become worse. Taken further when he becomes King Joffrey, loses what little oversight and restraint he had, and becomes a flat-out sociopathic Caligula.
  • Downplayed with Prince Quentyn Martell, who is sent by his father to woo Queen Daenerys. He's a descent and dutiful lad, but just doesn't have what it takes—not in looks or confidence—to win the heart of the World's Most Beautiful Woman, and gets himself burnt to death in an ill-judged attempt to win her respect by riding one of her dragons.
• Bryan in Summers at Castle Auburn is spoiled, hot-headed, cruel, and stupid. The only reason he isn't The Evil Prince is that he totally lacks political ambition.
• Tortall Universe: Prince Bronau in the Trickster's Duet is a family friend of the Balitangs, very affable, young, and handsome. He quickly starts flirting with Sarai and making the impression that he wants to marry her. He does, but only because she's a close royal cousin and he can use her name to legitimize his own claim if he can become the king's favorite, and to pay off his considerable debts. He loses the affability as soon as he's thwarted, tries to kidnap the child king after the old king dies, and then while attacking the Balitang house, kills Sarai's father. Hard to be less charming than that.
• A tricky variation in John Moore's The Unhandsome Prince. The titular Prince Hal is not this trope, but Caroline doesn't want to marry him — the reward for kissing the right frog is supposed to be a handsome prince and Hal is...well, not the thing girls dream about. His oldest brother, Prince Kenneth, on the other hand, seems like all Caroline could ask for except for the rudeness, the arrogance, the mean streak, the cruelty to animals, the utter ruthlessness...
• Prince Marek in Uprooted. Agnieszka is initially excited to see him riding up to the tower, as he's a famous war hero who's bravely fought numerous monsters from the malevolent Wood. Then when he gets there, he casually tries to rape her to get one over on her wizard teacher (she defends herself with magic and a heavy metal tray and notes that she probably would have said yes if he'd bothered to ask). After that, it's clear that he's a self-centered schemer who while personally brave, is also manipulative, spendthrift with other people's lives, and doesn't care what dirty tricks he has to pull to achieve his goal. (Which is, admittedly, the rather sympathetic desire to save his mother from twenty-odd years in the Wood.)

Live-Action TV

• Goodbye My Princess: Cheng Yin starts out as a relatively decent guy who genuinely loves Xiao Feng. Then he betrays and murders her grandfather within hours of their wedding. It all goes downhill from there. He still loves Xiao Feng, but his way of showing his love is to let his family torment her, pretend he hates her in a misguided attempt to "protect" her, and refuse to let her leave even when she makes it clear how miserable she is and how much she hates him. It ends with Xiao Feng killing herself.
• Alice: In this Syfy miniseries, Jack Chance is first seen as a normal, decent, Nice Guy when he proposes to Alice, until the Reveal mid-way, where he is shown to be Prince Jack Heart, the Big Bad's son. Also a Rebel Prince in a previously Arranged Marriage, helping Alice and the Wonderland Resistance to overthrow his mother. Later gets hit with a case of Wrong Guy First when Alice rejects his second proposal and hooks up with Hatter.
• The Crown': At first Diana is swept up in the excitement and glamour of her engagement to Prince Charles. It doesn't take long before she realizes she has absolutely nothing in common with him. Charles himself has serious doubts about marrying Diana, but his mother Elizabeth tells him a story about the arranged marriage of her own grandparents (actually using the phrase "Prince Charmless" to describe her grandfather) and how they grew to love each other, persuading him that the same thing will happen with Diana. Of course, we all know what happened next...
• Game of Thrones: King Joffrey Baratheon's actual personality after he drops his thinly-veiled chivalrous façade.
• Once Upon a Time has Prince James, the twin brother to the man who would eventually grow up to be Prince Charming. Calling the guy an arrogant, stuck-up Jerkass might be putting it mildly. His dad is no prize either.
• In Monty Python's Happy Valley sketch, the wise old king Otto has run out of suitors for the hand, and other desirable parts, of his daughter Princess Mitzi Gaynor. After killing off lots of princes of the Charming sort, the last standing suitor is Prince Walter. Walter is described as:
  ... rather thin and spotty, with a long nose and bandy legs, and nasty unpolished plywood teeth, and bad breath, and a rare foot disease. With a personality to match.
• On Mister Rogers' Neighborhood, Prince Tuesday would occasionally lapse into this, but it was justified in that he was supposed to be a child who still had a lot to learn, just like the target audience.
• Jessie: This is how Guy of the Week Brody is portrayed in Zuri's story in "The Princess and the Pea Brain": while he at first seems like a dashing prince, he "rusts his metal pants" and runs crying when faced with a dragon. As it turns out, his real-life counterpart is also a scumbag, going on a date with Jessie despite already having a girlfriend.
• Prince Cliff from The Other Kingdom is the fairy prince of Spartania. Unfortunately, he's snobby, pretentious, spoiled, immature, a total showoff and very insensitive to other people's feelings. And that's not even getting into trying to force Princess Astral into marrying him.

Myths & Religion

• The Bible:
  • In the Book of Genesis, the unnamed Shechemite prince who rapes Dinah, then decides after the fact that he's in love with her, and has his father ask her father to give her to the prince in marriage. Understandably, her family does not take this the way he intended.
  • In the Books of Kings, Prince Amnon, who lusts after his half-sister and rapes her, then casts her away in disgust, blaming her for causing him to lust after her. Naturally, his brother Absalom kills him for it.

Podcasts

• In Trials & Trebuchets, Prince Frederick, heir to the throne of the Kingdom of Ashua, is childish and dim-witted, which makes Serinepth find her unwilling betrothal to him that much more horrifying.

Puppet Shows

• In one of the Sesame Street segments, Kermit the Frog is trying to interview Cinderella while she's at the ball, but the Prince is so vain and self-centered, he keeps interrupting to talk about whatever he's wearing. Eventually, Cinderella runs off when the clock strikes midnight, leaving her glass slipper behind. The Prince is determined to find her, but not to marry her, but so he can have a matching pair... but then he drops the slipper and shatters. He just says, "Oh well. Easy come, easy go," and moves on to the next girl.

Theatre

• Into the Woods: Both Princes. They're clearly just after "hard to get" girls and lose interest after they've gotten them. Cinderella's prince cheerfully seduces the Baker's Wife into a quick fling, and in the end, both guys have moved on from Cinderella and Rapunzel to Snow White and Sleeping Beauty.
  "I was raised to be charming, not sincere."
• Portia's suitors in The Merchant of Venice. There's a scene where Portia and Nerissa consider them then dismiss them all. Only the Princes of Morocco and Aaragon get through to the casket lottery, but even then the Spaniard's usually portrayed as Ambiguously Gay and the Moroccan is usually played like he's on jehad. Of course, Bassanio's the only one for Portia.

Video Games

• Dragon Quest:
  • Dragon Quest V:
    • Prince Harry. When you first meet him, he's a six-year-old selfish prankster who only cares about himself, offering you to be his lackey (only to say you're not worthy of being one), and complains about how long you took when you and your father come to his rescue. After Pankraz's death and being enslaved by the Order of Zugzwang for ten years, he gets better.
    • His son, however, ends up being a carbon copy of his dad during the spoiled-brat phase, even going so far as to pull the same stunts on the main character's own children, though thankfully without any kidnapping occurring.
  • Dragon Quest VI: Prince Howard of Howcastle, who goofs around with village kids and forever runs from the cave of trials that every heir to the throne has to go through by a certain age. It takes no less than three false starts before the party finally drags him through the trials. However, the experience obviously impresses upon Howard the magnitude of the task, and he buckles down once the quest is completed.
  • Dragon Quest VIII: Prince Charmles is a particularly noteworthy example. In the localization, he's called "Prince Charmless" a lot (though he claims it's pronounced Charm-lay). As a character, he's a total Jerkass to cover up his Dirty Cowardice. Even Princess Medea uses the nickname at one point. He is given every opportunity to clean up and do the right thing. However, he seems to actively rebuke opportunities for Character Development, going so far as to cheat on the Rite of Passage that the party was already hired to help him with. In the end, it all comes back to bite him on his fat butt since his fiancée and would-be father-in-law were both present to witness his childish antics, tried to forcibly ride Medea while she was still in her horse form, and his father secretly catches him in the aforementioned act of cheating, costing him his engagement and whatever prestige he still had.
  • Prince Faris from Dragon Quest XI has a reputation as a brave and strong prince, but it's actually all just a lifelong Snowball Lie that has gotten increasingly difficult to maintain; he's actually a weak and cowardly young man who is introduced getting the hero to secretly take his place in a horse race because Faris himself is a lousy rider. Then when Faris is tasked with neutralizing the Slayer of the Sands, he once again convinces the hero to do it for him. The rather public collapse of the facade and a pep talk from Sylvando help him to start undergoing Character Development, though. It's also worth noting that in stark contrast to the other examples from the series, Faris deals with the player character as an equal, and always tries to honor his promises.
• Psychonauts has Dingo Inflagrante (AKA Dean LaGrante), a Jerkass Matador existing in the mind of Edgar Teglee who supposedly stole his love Lampita Pasionado (AKA Lana Panzoni) from him, according to Unreliable Narrators. When Raz meets the more Reliable Narrators, the story is clarified as Dean stealing Lana from him.
• In Warcraft Prince Arthas appears to be a classic good and noble hero. He's a paladin for the Light's sake. However, the game and particularly expanded universe materials reveal not only his slide into darkness but the fact that really? He was already a bit of a jerk. The paladins (other than Uther) never really liked him and make sure to point this out just before he kills them.
• In Puzzle Quest: Challenge of the Warlords, the player character has the option of helping Princess Seraphine run away from an arranged marriage to one of these.
• King's Quest:
  • King's Quest IV:
    • Edgar appears to be this but ends up being quite the subversion. As a deformed, hunchbacked Fae, he is too bashful to say much of anything, though he does end up talking Lolotte into sparing Rosella's life so Rosella can endure a Fetch Quest instead. After Lolotte has the treasures, he convinces her again to save Rosella's life via Standard Hero Reward. Then, he pulls a Heel–Face Turn by allowing Rosella a chance to escape, despite his case of Love at First Sight. Genesta's reward of changing him back to his true form completes his transformation into a Prince Charming.
    • A straighter example in the same game is the Jerkass that was bespelled into a frog. At least his frog crown is useful.
  • King's Quest VII also has a little of this, though only in passing. Although we never meet the prince in question, the intro features Valanice trying to talk Rosella into marrying one of the princes of another kingdom, who Rosella claims is "sooo boring".
• In Fairy Godmother Tycoon, one of the rival potioneries is the NSHP, or Not-So-Charming Princes. As the story progresses, they turn out to be nice fellows. Play your cards right, and they will marry Cinderella's Ugly Stepsisters (They're sweet while Cindy's a spoiled brat).
• In Miitopia, the Princess of Greenhorne is betrothed to the Prince of Neksdor, which is a disdainful, bratty utter douchebag, as well as a scaredy-cat Momma's Boy. It comes to bite him in the ass when the King of Greenhorne saw him fleeing and crying when his daughter got her face stolen, while her best friend bravely rushed out to save her despite being hopelessly outmatched. The King decided that said best friend would be a far more suitable husband for his daughter.

Web Animation

• The Little Painter has Prince Deja Vu, who spends his days eating, fencing, and being unpleasant.
• Played for Laughs in the Cyanide & Happiness short “Princess”, which shows a Princess Classic singing about how excited she is for her blind date with a prince, expecting him to be a Prince Charming. However, the prince turns out to be a Fat Slob who only cares about getting laid.

Webcomics

• Cursed Princess Club: Prince Frederick of the Plaid Kingdom starts off as one. While his two older brothers Blaine and Lance fall into the Prince Charming archetype and are also Lovable Jocks, Frederick is a bookish, unaccomplished non-athlete who graduated from his boarding school without honors and is The Un Favourite in the eyes of Plaid King Leland. He's initially excited that he and his brothers are getting Arranged Marriages with the princesses of the Pastel Kingdom, but he's shocked and repulsed that his own betrothed is the frightening and inhuman-looking Gwendolyn. While Gwen is just as much of a kind Princess Classic as her prettier sisters, Frederick is too put off by her looks to bother trying to get to know her, making the evening really awkward between the two. Eventually, he privately admits to Blaine that he finds Gwen "really ugly"; not only does Blaine slap him in the face and admonish him for saying something so mean, but Gwendolyn secretly overhears this and is very upset. The next day, his father furiously berates him and makes clear that Frederick will not get to back out of the marriage. From that point on Frederick reluctantly concedes that he should make at least a token effort to be nice to Gwendolyn. This leads him to gradually realize just how sweet Gwen really is, acknowledge how selfish he has been, and ultimately become much more charming than he started off.
• No Rest for the Wicked: Prince Ricardo a.k.a. "Dick the Picky". The words "Picky" and "Dick" pretty much describe his personality completely. He's something of a Grammar Nazi, and the Princesses he rescues tend to be somewhat ditzy. He also gave up on Sleeping Beauty because she snored. That is to say, rather than at least wake her up, he just walked out the way he came in, leaving her to her eternal sleep. In an unassailable castle no one had ever gotten into before. Nice move, Dick.
• Girl Genius: Martellus von Blitzengaard, Tarvek's cousin and the only real challenger to Tarvek's claim to the lighting throne is a brutish Spark who kidnaps Agatha, treats her like property, and experiments on her while she is asleep to make it so she physically can't live without him since he's decided to make her his queen. Agatha is rightly furious and despises him and comes up with a workaround to his despicable experiment very quickly.
• Saturday Morning Breakfast Cereal: Cinderella or someone like her starts to lose her interest in the prince once he starts peering at her feet and talking about how gross feet look in glass slippers.
• Prince Yuo from Dragon Sanctuary is immediately hostile towards Dean on account of him being a commoner who essentially stumbled into the nobility that the other Kiata's inherited, and also holds his fairy blood against him. He's also Nima's betrothed, though it's implied that neither of them had many options due to her mixed parentage and his personality.

Western Animation

• Avatar: The Last Airbender:
  • Avatar: The Last Airbender: Though his social rank is unclear, Yue's fiance is very much this. He's more interested in being a pompous braggart and making Sokka out to be a low-class rube than he is in... anything at all, really.
  • In The Legend of Korra, Prince Wu of the Earth Kingdom is a self-centered, vain Manchild and Casanova Wannabe. Subverted as despite his brattiness and immaturity, however, he is shown to have some Hidden Depths, being far more considerate towards commoners than his great-aunt, Earth Queen Hou-Ting, and after some humbling experiences, he is prepared to admit that he probably wouldn't make a very good king.
• The Legend of Zelda (1989): Prince Façade is so excessively concerned with appearances that he is willing to let Zelda get kidnapped instead of risking getting his clothes dirty.
• My Little Pony: Friendship Is Magic: Ever since "The Ticket Master", Rarity has hoped to meet "him," Princess Celestia's distant nephew Prince Blueblood. It is not until "The Best Night Ever" that she finally meets him in person during the Grand Galloping Gala. Unfortunately, Blueblood turns out to be a vain, stuck-up jerk, and after he uses Rarity as an equine shield against a flying cake, she finally gets fed up and chews him out for it. And this is after he's turned all the traditional courtesies on their heads because he's an Entitled Bastard who thinks It's All About Prince Blueblood. As the ponies are fleeing the gala, Rarity drops a glass slipper... and when Pinkie Pie points this out, she smashes it out of fear he'll use it to find her. To clarify the full significance of this: Rarity has always been shown to be a very dedicated social climber. Blueblood is so intolerable she's willing to completely torpedo her own reputation to dress him down properly. However, if Friends Forever 26 is any indication, he can be charming... just not to his own citizens.
• Not a prince, but in episode 3 of Scooby-Doo! Mystery Incorporated, Daphne's parents push her to go on a date with a snobby rich guy. He's late to the date, won't stop talking about himself, steals Daphne's food, and makes her pay the check. Needless to say, she ditches him real quick. And as a bonus, he's also the Monster of the Week
• In The Simpsons Treehouse of Horror episode "Wiz Kids" the class is practising "standard toad-to-prince spells". Milhouse's incantation is "slimy prince limey". That alone should be an indication of what kind of man the frog turns into. It should be noted, however, that Milhouse's Prince, a huge, fat John Falstaff Expy, is head and shoulders above Bart's attempt.
  "'Ow are ya, love? Give us a kiss then!"
• In Disney's propaganda short, Education for Death, we see a German retelling of Sleeping Beauty where the prince turns out to be Adolf Hitler.

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Alternative Title(s): Princess Charmless