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Molly: "JD, you just don't have that edgy mean streak that I'm attracted to."
JD: Shoves Turk into the bushes as he walks by "You were saying?"
Molly: "Sorry. I’m attracted to damaged, dysfunctional people, and you’re just too normal."
-Scrubs, "My Last Chance"

A hottie, usually in high school and usually male, whose first name is spelled t-r-o-u-b-l-e, often expressed through fondness for leather jackets and antisocial behavior. Has fangirls in both his own universe and the real one because All Girls Want Bad Boys. They may be revealed to have a heart of gold or a difficult home life, perhaps leading to a Very Special Episode. The female counterpart of Troubled But Cute is the Broken Bird.

See also: The Woobie, Draco In Leather Pants, Evil Is Cool, Evil Is Sexy, Dont You Dare Pity Me.
Examples:
  • Hollywood actor James Dean is pretty much the definitive example here.
  • Some might argue that Dr. Cox from Scrubs is an example of this. Troubled? He perpetually sees a shrink, regularly abuses the people he cares about, and is in love with a woman that he hates. Cute? He appears to be the only doctor in the place that regularly exercises, plus he's very proud of being forty and retaining all of his hair.
  • Jordan Catalano on My So Called Life.
  • Gabriel (and arguably most of Claire's love interests) on Six Feet Under.
  • Logan on Veronica Mars.
  • Dylan on Beverly Hills 90210.
  • Ryan Atwood on The OC. A bit of a subversion, as he was both the main character, and occasionally the Only Sane Man.
  • Michael on Roswell.
  • Jess on Gilmore Girls, who never actually got around to having a heart of gold.
    • Jess got to heart of bronze-silver alloy, but its a rather subtle thing.
  • John Bender in the mid-1980s Brat Pack film, The Breakfast Club
  • Subverted in Kim Possible: Ron tries to become this character, to get a date. It doesn't work, and through a little accidental A.P. he becomes a full-on supervillain.
  • Christian Troy on Nip Tuck. He's shallow, sex-obsessed, and in the habit of treating his sex partners like dirt — but he's also handsome, successful, and really good in bed, not to mention the unexpected vulnerable streak.
  • Jason Dean from the film Heathers fits this trope, though he eventually reveals himself to be a psychopath.
  • The Fonzie, from Happy Days, of course. Leather jacket? Check. Bad boy? Check. Heart of gold? Check. Three for three.
  • The Spider-Man movies' James Dean-esque version of Harry Osborn. At least before he was scarred in Spider-Man 3.
  • Danny Zuko (The Other Zuko) from the film/musical Grease
  • Zuko of Avatar The Last Airbender. The leather jacket wouldn't fit the medieval Asian "look" of the show, so he makes up for it with a facial scar linked to his tragic Back Story.
  • Warren Peace of Sky High, proving you can never go wrong with a Firebender with father issues.
  • Harima Kenji from the anime School Rumble takes a lot from this trope. Being rather antisocial and a juvenile delinquent, with a liking for wearing a leather jacket and riding a bike, beating up Yakuza goons, and all around looking ... except that beneath all that, he's an oaf with a heart of gold who likes drawing manga and is too scared to confess his love for a classmate. All while obliviously gaining the attention of several other girls.
  • Hayato Gokudera from Katekyo Hitman Reborn - a smoker, a delinquent, and a lover of high explosives. Naturally, the girls go wild for him.
  • Roger Klotz in Doug. He and Doug even get along once in a while, to show that he's not just a horrible jerk.
  • Sasuke of Naruto. Completely misses the look (or at least the dress code), though- that turtleneck, shorts and kneesocks fairly scream "scrawny kid". Then again, Ninja are supposed to cultivate an unassuming personal appearance, even if in fiction they usually don't.
  • Fakir from Princess Tutu. He even has a fanclub at his school, although it's likely none of his fangirls have ever talked to him, given his anti-social nature.
  • Dean from Supernatural. Sam is also getting there.
  • Seto Kaiba from Yu-Gi-Oh!
  • Vegeta from DBZ. Kinda cute, very troubled.
  • Jo from The Facts Of Life is a rare female example.
  • Most of the main cast of The Outsiders.
  • Sachiko from Maria Sama Ga Miteru arguably counts.
  • Squall Leonhart from Final Fantasy VIII (although he actually graduated early in the game).
  • This trope is mocked through Zeke in Disney Channel's movie Minute Men, when girls come up to him and ask, "You know, you're kind of scary and unapproachable... can we sit with you?"
  • Kyo Sohma from Fruits Basket, an antisocial martial artist who's obsessed with beating Yuki. Tohru seems to genuinely like him, though, and in his defense he does have a good Freudian Excuse.
  • Fans of Repo! The Genetic Opera are divided on whether Grave-Robber is Troubled But Cute, or just antisocial and very, very pretty.
  • Sean Hunter in Boy Meets World. The rampart trailer park trash jokes started as innocent and one dimensional character traits. Then for a good while from season two onward, it seemed like every other episode was a Sean pity-party fest. And he got girls to boot.
  • Batman, as epitomized here in Justice League Unlimited, where he's trying to convince Wonder Womanwhy they they wouldn't be good together:
    Batman: "You're a princess from a race of immortal warriors. I'm a rich kid with issues. Lots of issues."
  • Edward Cullen, in Twilight. The actor who plays him in the movie certainly believes this, describing him as "self-loathing" and a "108-year-old virgin".
  • Joe "The Condor" Asakura in Science Ninja Team Gatchaman.
  • Atton in Knights Of The Old Republic II.