The best role that was played by Brad Pitt, in my opinion, was Ocean's Eleven. He played a con man alongside some other really great actors. I like him in that movie the best because it was a complicated role. There was a lot of substance to the movie and to the role he played as well. He is great in everything. He is very diverse and talented. But, I think Ocean's Eleven was his ultimate movie for a number of reasons.
I feel he gave that role his all. When he acted alongside Jolie, I felt he was a bit nervous. I was on edge. I still liked those shows but I think he was more relaxed and more in his element when he was on Ocean's Eleven. I like him in comedy roles too, like The Mexican. Still, his performance in Ocean's Eleven easily takes the cake in my book.