Penn won an Oscar -- deservedly so -- for his devastating portrait of a grieving parent in Clint Eastwood's melancholy drama.
You know and love the cast of Ridgemont High, particularly Penn's Spicoli, the film's most excellent slacker and stoner.
There's no happy ending for Penn's convicted killer. But there is a moving portrait of a complex man that's worth watching.
In an underrated mob movie, Penn hangs with (and maybe even outshines) Al Pacino in his own genre.
Penn fully transforms himself into optimistic city supervisor Harvey Milk -- the first openly gay man elected to political office.
Penn is the emotional center of this jigsaw puzzle of a movie, as a guilt-ridden man with another man's heart, desperate for redemption.
Two great character actors -- Penn and Christopher Walken -- collide as father and son, with typically great results.
This underrated political thriller with Nicole Kidman explores intrigue (and assassination attempts) at the United Nations.
Don't think Sean Penn is funny? He proves you wrong in this tongue-in-cheek Woody Allen comedy.
Penn plays brilliantly against type. He's not grim but rather motormouthed, coke-addled, and hyperactive.