Best as the young con man in Thelma and Louise. Pretty good job as the crazy son in 12 Monkeys.

The anti-materialism radical/extremist/illusion, Tyler Durden, in Fight Club. That was a superb film that had volumes to say about the emptiness and stupidity of the modern American consumer mindset.

Michael Sullivan in "Sleepers".

Are you kidding me? Since when is he a great actor? Granted, a great movie star but actor? He's extremely good looking, can read and talk and smile. He can carry his two-dimensional charactors very well. Just, a very mediocre actor. He seems to be the same guy in each and every movie he does. Yawn.

my favorite movie is the first one i ever saw him in and that was thelma and louise

He's probably my favorite actor at this point, but I haven't liked all of his movies. My favorite movie being Devil's Own

While I'm not overly impressed with any of Brad Pitt's work, I would say his best role was Joe Black in the film Meet Joe Black. Since you wouldn't expect death to have a lot of emotion or flourish, Pitt's sometimes wooden acting fit the part perfectly.

His character in A River Runs Through It.