Mystic River
Rank Title Points Votes Your Vote
1
Penn won an Oscar -- deservedly so -- for his devastating portrait of a grieving parent in Clint Eastwood's melancholy drama.
Current Score:
207
Total Votes:
523
2
You know and love the cast of Ridgemont High, particularly Penn's Spicoli, the film's most excellent slacker and stoner.
Current Score:
96
Total Votes:
466
3
There's no happy ending for Penn's convicted killer. But there is a moving portrait of a complex man that's worth watching.
Current Score:
88
Total Votes:
418
4
In an underrated mob movie, Penn hangs with (and maybe even outshines) Al Pacino in his own genre.
Current Score:
75
Total Votes:
405
5
Penn fully transforms himself into optimistic city supervisor Harvey Milk -- the first openly gay man elected to political office.
Current Score:
23
Total Votes:
429
6
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.
Current Score:
-17
Total Votes:
361
7
Two great character actors -- Penn and Christopher Walken -- collide as father and son, with typically great results.
Current Score:
-17
Total Votes:
343
8
This underrated political thriller with Nicole Kidman explores intrigue (and assassination attempts) at the United Nations.
Current Score:
-75
Total Votes:
303
9
Don't think Sean Penn is funny? He proves you wrong in this tongue-in-cheek Woody Allen comedy.
Current Score:
-104
Total Votes:
282
10
Penn plays brilliantly against type. He's not grim but rather motormouthed, coke-addled, and hyperactive.
Current Score:
-135
Total Votes:
267