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alt title(s): Cute But Troubled
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:

Anime and Manga

Film
  • Roger Davis from Rent. The guy has HIV and is really, really cranky, but is still beloved by any straight girl.
  • John Bender in the mid-1980s Brat Pack film, The Breakfast Club
  • Jason Dean from the film Heathers fits this trope, though he eventually reveals himself to be a psychopath.
  • 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
  • Warren Peace of Sky High, proving you can never go wrong with a Firebender with father issues.
  • 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?"
  • Fans of Repo! The Genetic Opera are divided on whether Grave-Robber is Troubled But Cute, or just antisocial and very, very pretty.

Literature
  • Most of the main cast of The Outsiders.
  • 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".
  • Sirius Black in Harry Potter, though rather than being antisocial he is represented as inexplicably popular despite various acts of cruelty. At least as an adult though, he is a good person at heart.

Live Action TV
  • 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.
    • Both The Todd and Turk have been shown as regularly working out at the hospital. That said, Cox is rather studly.
  • Jordan Catalano on My So Called Life.
  • Gabriel (and arguably most of Claire's love interests) on Six Feet Under.
  • Logan on Veronica Mars.
    • Not to mention Weevil, a gangster who loves his grandma and fell for a certain blonde.
  • Dylan on Beverly Hills 90210.
    • Liam is another textbook example on 90210, especially as they're now setting him up for a fling with good-girl protagonist Annie.
  • Titular character from House. Both in-universe women and fangirls seem to adore him. Well, he is played by Hugh Laurie, who seems to fit this trope in real life as well.
  • 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.
      • He probably would have gotten the heart of gold if they hadn't put him on a bus to California to live with his biological father in order to set up a spinoff that never happened. Ugh.
  • 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.
  • Fonzie, from Happy Days, of course. Leather jacket? Check. Bad boy? Check. Heart of gold? Check. Three for three.
  • Dean from Supernatural. Sam is also getting there.
  • Jo from The Facts Of Life is a rare female example.
  • Shawn 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 Shawn pity-party fest. And he got girls to boot.
  • Tim Riggins, drunkard and resident Estrogen Brigade Bait on Friday Night Lights.

Tabletop Games

Video Games
  • Squall Leonhart from Final Fantasy VIII (although he actually graduated early in the game).
  • Atton in Knights Of The Old Republic II.
  • Inui Arihiko in Tsukihime until Shiki stole all his luck with girls away, which made him a little bitter. Instory, Shiki himself might actually count despite practically being a paragon of virtue. However, he actually tends to scare people due to familiarity and closeness to death. Yet the same people find themselves falling in love with him (Satsuki, Arcueid, Akiha etc.) regardless.

Western Animation
  • 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.
  • 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.
    • What about Jet?
  • Roger Klotz in Doug. He and Doug even get along once in a while, to show that he's not just a horrible jerk.
  • Batman, as epitomized here in Justice League Unlimited, where he's trying to convince Wonder Woman why 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."
  • In one episode of The Simpsons, Millhouse temporarily became one of these, complete with anti-socialness, a leather jacket and fan-girls.
  • Terry Mc Ginnis a la Batman Beyond seems to be this in the first couple of episodes before he opens up and reveals that he's actually a responsible, altruistic young man.

Real Life
  • Hollywood actor James Dean is pretty much the definitive example here.
  • Ted Bundy was very adept at courting the opposite sex. Too bad he was evil.