Christian Stovitz (Justin Walker)
Alicia Silverstone's Cher plans to lose her V-card to this wry aesthete until she realizes he's "a disco-dancing, Oscar Wilde�reading, Streisand ticket�holding friend of Dorothy." Best line: "The jacket�is it James Dean or Jason Priestley?"
The chubby outcast helps Cady (Lindsay Lohan) adjust to suburban high school society after her family moves to America from Africa. Best line: [to a short girl trying to kick him out of the girls' restroom] "Oh my God -- Danny DeVito! I love your work!"
Danielle (Juno Temple) and Clarke meet when an assignment casts them as parents to a flour-sack baby. Best line: [in reference to football players] "I like the way they smell like Bengay and ferns."
John 'Plato' Crawford
Rebel Without a Cause
When Jim (James Dean) enrolls at Dawson High, sheepish Plato quickly falls under his spell. Best line: 'I had to go to a head-shrinker. I only went twice though. My mother said it would cost too much, so she went to Hawaii instead.'
Phil �Duckie� Dale (Jon Cryer)
Pretty in Pink
Didn't we all have an Andie in high school? It didn't take keenly tuned gaydar for Molly Ringwald to see through Duckie's overzealous mooning ("I live to like you!"). Best line: "This is a really volcanic ensemble you�re wearing."