Emilio Estevez and Ally Sheedy as Andrew Clark and Allison Reynolds in "The Breakfast Club"
Allison Reynolds, The Breakfast Club (1985) Played By: Ally Sheedy
To the credit of John Hughes and Ally Sheedy, Allison Reynolds is one of the most believable loners on this list. In spite of her model looks, the actresses's matted hair, random outbursts and habit of attending detention at-will made her a convincing basket case.
Boy in Police Station, Ferris Bueller's Day Off (1986) Played By: Charlie Sheen
Even with his Adonis DNA (his words, not Movieline's), Charlie Sheen nailed his role as the wise police station drug addict in this '80s classic. Credit the intense stare, shifty eyes, and general Charlie Sheen-ness. Whatever he did with Jennifer Grey off-set is another matter entirely (Sheen said the first star he ever slept with was Dirty Dancing's Jennifer Grey).
Heath Ledger kissing Julia Stiles (Patrick Verona and Kat Stratford) in "10 Things I Hate About You" (1999)
Patrick Verona, 10 Things I Hate About You (1999) Played By: Heath Ledger
Heath Ledger may have been beautiful, but his 10 Things I Hate About You character was a gruff, angsty teenager who smoked in pool halls and made money off of dating other outcasts. As such, he qualifies as one of the sexiest loners on this list.
Donnie Darko, Donnie Darko (2001) Played By: Jake Gyllenhaal
Unlike most of the characters on this list, Jake Gyllenhaal's disturbed Donnie Darko legitimately earned his loner status, as does anyone else who has visions of demonic rabbits.
Christian Slater and Winona Ryder as J.D. and Veronica in "Heathers"
J.D., Heathers (1988) Played By: Christian Slater
As most high school films featuring attractive outsiders tend to do, Heathers justified that the attractive J.D. was an outsider because he was new to town. Unlike other high school films, J.D. perpetuated his outsiderness by pulling guns on classmates and feeding his peers drain cleaner.
Cady Heron, Mean Girls (2004) Played By: Lindsay Lohan
In spite of her good looks, Cady Heron does not fit in because she was homeschooled in Africa by her zoologist parents. But because of those same looks, she is also able to infiltrate the popular clique by forfeiting her own values and putting together a slutty Halloween costume.
Olive Penderghast, Easy A (2010) Played By: Emma Stone
Our favorite kind of outcast on this list, Emma Stone's Olive Penderghast learns to embrace her new status as the school "skank" and is (almost) completely unconcerned about her peers' perception of her. Source: www.movieline.com