Thelma and Louise (1991)

Brad had a kind of cute but dumb vibe going in his small role here, taking advantage of the naive Thelma (or was it Louise?) and inadvertently spurring their ill-fated crime spree.

Interview with the Vampire (1994)

Brad played a brooding bloodsucker (years before David Boreanaz made the type popular on Buffy the Vampire Slayer) in this supernatural buddy picture. Also features Tom Cruise, Kirsten Dunst and Antonio Banderas as his fellow creatures of the night.

12 Monkeys (1995)

Brad scored an Oscar nomination for playing a madman with apocalyptic tendencies in this bleak but intriguing sci-fi tale from director Terry Gilliam. I lost count of the monkeys, but I'm pretty sure there are actually 12.

Seven (1995)

The movie's kind of over-rated, but Brad is good playing an ambitious New York cop on the trail of a sin-obsessed serial killer. As in Spy Game, he's paired with an older, wiser partner, this time Morgan Freeman.

Fight Club (1999)

Brad re-teamed with director David Fincher (Seven) to play a man with a mission. That mission: to persuade other men to beat the crap out of each other because . . . well, just because.