Some who played geeks while they were in their teens evolved to be really attractive in their thirties. Who would have thawt they'd grow up to be so hawt?
Geek Role Graduates
Sarah Jessica Parker is today a fashion icon, best known for her Carrie Bradshaw in Sex and the City (1998-2004).
Carrie is far stretch from her earlier persona, the social misfit Patty Greene in Square Pegs (1982-83).
Anthony Michael Hall solidified the 80's teen-movie geek archetype in films such as Sixteen Candles (1984), The Breakfast Club (1995) and Weird Science (1985). In a refreshing twist, he played Wynonah Ryder's buff, blonde jock boyfriend in Edward Scissorhands in 1990. In 1999, he momentarily returned to his geek-role roots as Bill Gates in Pirates of Silicon Valley. His biggest recent claim to fame is lead role Johnny Smith in The Dead Zone (2002-2007). He was also in The Dark Knight (2008) as TV reporter Mike Engel.
John Cusak played the socially challenged Bryce in Sixteen Candles (1984), one of those various geeks in the company of Farmer Ted (Anthony Michael Hall). Five years later he played the male lead (that is, an unpopular but lovable-once-you-get-to-know-him boy who falls in love with the pretty, popular girl) in one of the most well-loved chick flicks of all time, Say Anything (1989). In the 90's, he graduated into more mature roles as in Grosse Pointe Blank (1997) and Con Air (1997). He's also known as the slightly-hunky-slightly-awkward romantic in films such as America's Sweethearts, Serendpity (2001) and Must Love Dogs (2005).
Robert Downey Jr. was one of the nerdy perverts in Weird Science. Rumor had it that he was one of the original picks for the role of Molly Ringwald's geeky best friend, Duckie in Pretty in Pink (1987), second choice to Anthony Michael Hall (The part was finally given to Jon Cryer).
Downey was easily spotted as a cutie in his twenties, playing the hot, romantic lead in chick-flicks like Chances Are (1989) and Only You (1994).
He, like John Cusack, seems to have a liking for offbeat roles. His most badass role though has got to be Iron Man (2008).
Can you get any geekier than Patrick Dempsey's Ronald Miller in Can't Buy Me Love (1987)? After years of temporarily fading into the background, he evolved and re-emerged as a TV hottie, beginning with a recurring role in Will and Grace (1998). He is of course best known as Dr. Derek "McDreamy" Shepherd in Grey's Anatomy.
Tai of Clueless (1995) wasn't exactly a geek but was more of a dork - unattractive and unpopular.
After a real-life makeover, Brittany Murphy turned out to be quite a bombshell, as in gorgeous enough to be cast opposite Ashton Kutcher in Just Married or as that sexy waitress in Sin City.
Even as a geek, she was cute. Oscar Winner and cinema sweetheart Reese Witherspoon is now unmistakably glamorous. Back in 1999, she played the neurotic, power-hungry A-student Tracy Flick in Election, and the reserved virgin Anette Hargrove in Cruel Intentions.
