Twelve Monkeys (1995): Here’s my crazy theory: The funniest person on the planet is secretly Brad Pitt. He has not had, nor made for himself, many chances to prove this, meaning this is really more of a notion than a rigorous hypothesis. But in his too few films where he’s overtly comic he has proven himself a supremely odd duck who could be the world’s funniest human—if he’d stop making so many “serious” movies like Babel and Benjamin Fucking Button. (He should still appear in actual serious movies like The Tree of Life and The Assassination of Jesse James.) Case in point: his absurdly alert turn as a wealthy lunatic in Terry Gilliam’s riff on La Jetée, a performance imploding with spastic movements and bizarro line readings. When accepting his Golden Globe, he thanked Kaopectate for doing “a great service to their fellow man.” See? Brad Pitt is weird.
Snatch (2000): As a heavily tattooed gypsy, Brad Pitt is so indecipherable he might as well be speaking a language he made up—like Jodie Foster in Nell, only way more inspired.
Ocean’s Twelve (2004): In Eleven and Thirteen, Pitt mostly relies on cucumber cool deadpan. In Twelve, with more time to shine, he actively goofs off, ostentatiously eating food in every scene, making strange faces for Steven Soderbergh to freeze frame on and responding to a touchy question from Matt Damon with the words, “It’s not in my nature to be mysterious. But I can’t talk about it, and I can’t talk about why.”
Burn After Reading (2008): Few things make me instantly happier than Pitt’s endearing idiot bouncing back and forth, exclaiming, “I got his number!”
Inglourious Basterds (2009): Pitt is clearly having the time of his life doing his finest Foghorn Leghorn accent and seeing how many “i”s he can fit into the word “oblige.”
Moneyball (2011): This isn’t a comedy, and there’s plenty of “humanizing” scenes of him bonding with his daughter. But as renegade General Manager Billy Beane, Pitt is delightfully eccentric, delivering Aaron Sorkin dialogue with a cool idiosyncrasy that throws off every character. More please.
"Pan" deserves the hook
Matt Damon delivers in "The Martian"