One of the truly great actors of his generation.

Which of the listed performances do you think is his BEST work?

Shouldnt Haiti be there as well?

A tough choice, and I haven't seen several of his highly acclaimed roles from the list. I went with Mystic River.

I think I Am Sam is his best performance, but Mystic River is my favorite movie he's been in.

U-Turn.
"40,000 people die every day, Darrell. How come you're not one of 'em?"

Dead Man Walking although his turn in Fast Times is right behind it.

Dead Man Walking

Wow, I think I've only seen two of those films. Keep meaning to see most of the others, but there are just too many films and too little time.

Dead Man Walking

Or the one for acting like a douchebag?

But he went full retard.

Voted Dead Man Walking.

Curiously, I recently watched two Sean Penn movies where he did not deliver a good performance: Shanghai Surprise and Crackers. The fact that both movies were duds didn't help either.

Hmmm...quite a few movies here I've yet to see, so I'm voting for Carlito's Way.

Dead Man Walking contains his career-best performance.

haven't seen Dead Man Walking in a very long time, but i remember not loving the movie. even though i didn't love the movie as many have, i thought he was great in Mystic River and the last scene when he looks at Kevin Bacon was just classic.

Dead Man Walking

Fast Times followed by Bad Boys, while his most underrrated performance is Casualties of War.

Mystic River. Great performance in a very good film. Even as a kid I didn't think Jeff Spicoli was funny.

Well then I guess I will choose the one with you, the douchebag

I choose this one. One of my 2 or 3 least favorite actors of all-time. A total ham on-screen that overacts in everything he does.

Milk

There may be more obvious choices but Spicolli is easily his most legendary character.

the seedy fro lawyer of carlito's way no question who was also an influence on GTA vice city.