86. MATT DAMON
The Talented Mr. Ripley (1999)

Two years after scoring a Best Actor nomination (and a Best Screenplay Oscar) for Good Will Hunting, Damon delivered his gutsiest performance to date as Tom Ripley, the jealous nerd who fixates, with fatal results, on gilded playboy Dickie Greenleaf (the excellent — and nominated — Jude Law). The treacherous turn earned him nominations from the Golden Globes and the MTV Movie Awards (as Best Villain), but the Academy left Damon still hunting for a follow-up nod.