James Spader (Pretty in Pink)
Every high school has its jerks, and James Spader played one to perfection in
Pretty in Pink. As feather-haired rich kid Steff—best friend of fellow rich kid Blane (Andrew McCarthy)—Spader creepily and secretly pursues Andie (Molly Ringwald) in the film, while calling her a “mutant” in public. After
Pink, he went on to win accolades for his role in 1989’s
Sex, Lies, and Videotape. And more recently, a balder, bespectacled Spader has starred in
The Practice and
Boston Legal, earning him three Emmy Awards.