I think Pitt is a better actor than he generally gets credit for. Despite being a handsome, famous, rich movie star who's married to a sexy, famous movie star he's self-deprecating enough that you don't hate him the way we probably should. He's a little less successful at it than pal and
Ocean's co-star George Clooney, but they are similar in that way. To his credit Brad doesn't really take the safe, easy, glamorous movie star kinds of roles, and if he does move in that direction it is undercut by humor and a sense that he isn't buying into this sex symbol stuff either. I think you can see this early on.
After his breakthroughs in
Thelma & Louise (1991) and
A River Runs Through It (1992) he went and played ugly and weird in
Kalifornia (1993) and that hysterical small stoner part in
True Romance (1993).
Interview with the Vampire (1994) was a big movie and
Legends of the Fall (1994) is the closest to a classic handsome leading man thing he had done, even with that dark last act. But then choosing the very dark
SE7EN (1995) and Gilliam's
12 Monkeys (1995) were right back against what I'm sure agents and managers were begging him to do, but of course they paid off when
SE7EN became a $100-million hit and
12 Monkeys garnered him his first (and to date only, as an actor) Oscar nomination.
The next few years were not successes after disappointments in
Sleepers (1996) a big awards-bait movie with an all-star cast and crew that just wasn't very good,
The Devil's Own (1997) with that horrible Irish accent and dull and predictable plot, the sincere but unwieldy
Seven Years in Tibet (1997) and a re-make that should have worked on paper but was a screaming bore on the screen with
Meet Joe Black (1998). Besides being dull, I think a big problem with
Joe Black was that Pitt played too pretty and purposefully had no personality, which frankly he didn't pull off. But he seemed to learn quickly from those mistakes and came roaring back in
Fight Club (1999) which was a pitch black satire where he got to play sexy but also (and importantly) weird and dangerous. Then came
Snatch (2000) where again he's got reason to take off his shirt and show his six pack off, but he's also very funny and dirty and weird. He also learned a big lesson from
Devil's Own and this time the accent is an intentional joke. But as much fun as that role mostly is, in the scene where he's watching the camper burn you do see the emotional truth and pain underneath the fitfully amusing histrionics.
I thought
The Mexican (2001) was fun and unfairly ignored, and being a character who was incredibly attractive but just plain not very bright or competent suits him perfectly. I thought Tony Scott's
Spy Game was pretty tedious stuff and I just don't buy Pitt as the straight up hero type. If he's a fu*ked up goofball who happens to look like Brad Pitt and manages to succeed, great, but there has to be an element of humor or some serious flaws to go with that pretty face. Everybody seems to be having fun in the
Ocean's series, especially Pitt and Clooney who get to have fun playing with those slick movie star images that
People Magazine really want them to embrace. I thought Wolfgang Petersen's
Troy (2004) was a spectacular bore, and again I don't buy Brad Pitt as the brooding super hero. I just don't. And that's what makes
Mr. & Mrs. Smith (2005) work so well, that he adds humor to the dashing super spy and makes him so much more enjoyable to watch.
With
Babel (2006),
The Assassination of Jesse James by the Coward Robert Ford (2007) and Fincher's upcoming
The Curious Case of Benjamin Button he's improving his range even more and finding dramatic parts to sink his acting chops into. And the Coen Brothers' next,
Burn After Reading, promises to be more of the good-looking but self-deprecating thing which is his true bread and butter. I'm sure there are agents and producers in Hollywood who think he's nuts for not doing straight ahead Romantic Comedies and formulaic weepers, but he knows what he's doing.
So, as for which of those I think are his best performances to date...
1.
SE7EN
2.
Babel
3.
The Assassination of Jesse James
.......by the Coward Robert Ford
4.
The Curious Case of Benjamin Button
5.
Fight Club
6.
The Mexican
7.
12 Monkeys
8.
Burn After Reading
*updated to include his 2008 films
And I love his small roles in
True Romance (for me the first big screen comic stoner post-1982 who wasn't just doing a Jeff Spicoli impression) and
Thelma & Louise, as well as his cameos in
Confessions of a Dangerous Mind and
Full Frontal.