I think this has to do with Pitt rising to prominence just before the Superhero Craze of the 2000s. I can imagine a world where he is the 1st on the list for Superman or Captain America or even Batman. But like his similarly chiseled but respected colleague Matthew McConaughey, he narrowly escaped the fate that awaits Henry Cavill or the Chris-es Hemsworth and Evans.
1. Se7en (1995; David Fincher)
In the 1990s, Pitt established himself as a respectable supporting actor, and even earned his first Oscar nom for his work in 12 Monkeys. In Se7en, he plays Det. David Mills, the young hotshot cop contrasted to the more world-weary Somerset, played by Morgan Freeman. What's remarkable about Pitt's performance here is that it isn't very showy. I myself had trouble in figuring out how to describe and qualify it. Pitt is more concerned with making his character gel with his surroundings than putting in a show-stopper of a performance. Pitt is a surprisingly restrained actor but I think it's because he likes to really wow the audience when he drops the restrain like during the famous "what's in the box?" climax of Se7en.
2. Troy (2004; Wolfgang Petersen)
I mentioned earlier that Pitt gets taken seriously as an actor because he so rarely uses his looks as a crutch. Of course, the big counterpoint to that argument is Troy, where he is the most beautiful member in a cast that includes the crazy-hot ladies Diane Kruger, Julie Christie and Rose Byrne. In the grand scheme of his career, I can't quite place Pitt's performance as Achilles in this retelling of the Helen of Troy story (also called The Iliad). This is definitely a star performance but in a way that Pitt hadn't done before and hasn't really done since. This isn't Pitt disappearing into the character, this is BRAD PITT, MOVIE STAR in a toga carrying a sword. No, I wouldn't count his work here as some of his finest--but I think that's because this movie is focused on being epic and not on crafting fascinating characters and plots.
3. Burn After Reading (2008, Joel and Ethan Coen)
One thing that really fascinates me about Brad Pitt is that he can do a movie like Troy where he is the star of the show and then he can do a movie like Burn After Reading, where his role is just an extended cameo. Of course, one of the tricks of Burn After Reading is that it makes you think that Pitt is the star of the show and his departure from the film is one of its most shocking yet hilarious moments. As Chad Feldheimer, Pitt is playing such a ridiculous, cartoonish character and he really commits to the ditzy, dumb Chad and his quirks. For me, it was weirdly cool to see Pitt play a character that would normally go to someone less A-list. Like I said, Pitt so rarely goes over the top, but when he does in this movie, it's incredibly effective.
Pitt's commitment to his oddball character in Burn After Reading was really just a precursor to his brilliant work in Inglourious Basterds. As Lt. Aldo Raine, Pitt again brings out his goofy charisma but then mixes it with an unnerving menace. There are a lot of laughs to be found in his performance (like how he pronounces the word Nazi) but at the same time, there's something really unsettling about the glee he takes from scalping Nazis. Pitt's natural charm and A-list persona get us on his side but the danger in his performance confronts us with our own revenge fantasies. It is truly a sublime performance. At first I wondered why someone of Pitt's clout would take on such a small role, where he plays second fiddle to the unknown at the time Melanie Laurent and Christoph Waltz. His small role wasn't meant to dupe the audience like in Burn After Reading. Such a challenging balancing act between comedy and menace, however, required an actor of Pitt's calibre.
5. Moneyball (2011; Bennett Miller)
As in awe as I am of Pitt's work as Aldo Raine, his most grand achievement as an actor was as Billy Beane in Moneyball. What makes this performance better than the others listed is that it's incredibly naturalistic. His work feels lived-in and nuanced, as if he's been playing Billy Beane for years or, rather, has been Billy Beane for years. Though Pitt exploits his inherent charm and coolness in the role, underneath all that is the crushing disappointment of unrealized potential. Pitt channels the tragedy of Beane's past into his aggressive belief in the moneyball system. It's also quite ingenious the way Pitt shows Beane taking off his GM mask and becoming a devoted father when with his daughter. This suggests that his baseball team isn't everything, even though he's ready to put everything on the line to save it. I was severely disappointed when Pitt lost the Oscar to Jean Dujardin at the 2012 Academy Awards because his work here was effortless and authentic but I guess that's not the kind of thing the Academy goes for these days.
Other remarkable films starring Brad Pitt:
1. Ocean's 11, 12 and 13
2. Fight Club
3. The Assassination of Jesse James by the Coward Robert Ford
4. The Tree of Life
5. The Curious Case of Benjamin Button
Look out for part 7 of "5 Films" starring the great and powerful Charlize Theron.
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