What movies should I watch that best displays his amazing actor-ness, because I have yet to see something that really showcases his talent.

MILK!
Did you see that? He was great.

Mystic River was supposed to be good- never saw it, though.

http://imdb.com/name/nm0000576/

Never saw Mystic River, but his performance in I Am Sam was excellent.

I disagree with Milk. I saw his performance in Milk, and his voice and gestures constantly reminded me of I Am Sam, where he portrays a man with the IQ of a seven-year-old.

21 grams
assassination of richard nixon

are 2 of his better lesser known films

sean penn best movie- Fast times at Ridgemont high
george clooney best- Facts of Life


These are the roles they were meant for, they are not nor will they ever be in the calibur of Clark Gable, Charlton Heston, Clint Eastwood etc...

I too have always thought Sean Penn was pretty overrated and pretentious. And I'm really, really tired of the whole humanitarian thing...

That said, 21 Grams is a phenominal movie in every way. I would say its Penn's best, and reminds me why people say he is so good.

Fast Times and Ridgemount High is great as well. When the teacher shows up at his house is a classic scene!!

Penn is a wonderful actor, and so was his star turn as Harvey Milk.

But I thought that Mickey Rourke should have won the Oscar this year, and here's why.

As believable as Penn's work was in Milk, it had a lot to do with affectation rather than digging to the ragged core of his being, as Rourke did in "The Wrestler."

I have always admired Penn's work, but perhaps it was his early work really gave us a preview of that dangerous, edgy quality that later morphed into his more mature movie roles. Films like, "Bad Boys," "At Close Range," etc. where he displays that raw edge of disaffected youth that really opened the doors of his early entry into the industry.

www.robertkim.com

wow are you serious well everybody has there opinion and reasons... some people think will smith is great and others think he sucks presonally i think sean penn is a first rate actor

Sweet & Lowdown is another good one I forgot about.

I can't say I'm a huge fan of his and haven't even seen "Milk" yet but I did think his work in "Dead Man Walking" was really excellent.