Brad Pitt’s Best Performances Ranked

By | March 22, 2020

[Virus note: Hey, the quarantine and self-imposed isolation is kicking into its 2nd or 3rd week for some of us. We have to pass the time somehow…I’ve seen people on Twitter start troll fights over which Kool-Aid flavor is best, so this isn’t the worst use of time.]

Brad Pitt might’ve won his Oscar for “Once Upon a Time in Hollywood,” and he definitely deserved to, yet I can’t help but feel there are a few better performances of his out there. This was a very, very tough list to put together, as Pitt has a lot more great performances than most people realize, and I couldn’t find room for even some of his most acclaimed work (“A River Runs Through it,” “Seven,” “Babel,” and a better-than-you-remember lead in “Meet Joe Black”).

Honorable Mentions: “Kalifornication,” “Thelma and Louis,” “The Curious Case of Benjamin Button,” and “12 Monkeys”…Pitt first showed an interest in doing wilder, more challenging work as a Southern-fried serial killer in “Kalifornication,” but I think he does “brash, violent redneck” a lot better in “Inglorious Basterds,” and “Jesse James.” “Kali” is more like a warm-up for better things to come when he’s a little more nuanced. “Thelma” was inarguably Pitt’s breakout role, and he’s solid in it, but it’s a small part, and there were 12 other films where I thought he was given a little more to do. Finally, just to show how tough this list was to cultivate, “Benjamin Button” and “12 Monkeys” are two of Pitt’s four Oscar nominations, but ultimately some other work was better. In the case of “Button,” there was a different 2008 performance that I thought was livelier and “Monkeys” is one of those “Kalifornication”-wildman performances (he’s literally playing someone absolutely nuts) that are fun, but I think he does it in a little bit more subtle and fully formed way later on…

12. “Ocean”‘s trilogy…Sure, Pitt is asked to play “smooth” a lot in his career (“Spy Game,” “Thelma,” “Hollywood,” and of course “Mr. and Mrs. Smith”) but when you really look at his filmography, it’s almost amazing how often he bucks against this, playing weirdos, killers, repressed vampires or death himself, bitter fathers, and anything else you can imagine. The “Ocean” movies are one of the very few times he stops trying to fight his inner Steve McQueen, and embraces it to deliver a performance that is (to be brutally honest) more charismatic than anything McQueen was actually capable of. My favorite of the three is “Ocean’s Twelve,” where his European romance with Catherine Zeta-Jones generates unbelievable chemistry–and is everything the “Thomas Crown Affair” should’ve been, but wasn’t really.

11. “Snatch”…A lot of A-list actors get stuck in a rut. I mean, there’s only so many times you can watch Tom Hanks play “based on a true story” captains or Tom Cruise completely give up on anything outside his comfort zone post-2004’s “Collateral” or maybe 2008’s “Tropic Thunder.” Pitt isn’t one of those actors, as I’m pretty sure no one thought he’d star as an indecipherable gypsy boxer in a Guy Ritchie in 2000, at the height of his fame.

10. “Inglorious Basterds”…For almost any other actor, Lt. Aldo Raine would be their most iconic character and a career-high performance. For Pitt, it’s his tenth best work, and one of many huge hits that made a lot of money and received universal critical acclaim. Although Aldo is hugely enjoyable, there’s something a little cartoony about it that–while intentional–is more fun than truly excellent.

9. “Burn After Reading”…Although the film itself is just okay (it’s more Coen Brothers misanthropy, as they hate their characters more than any director not named Gaspar Noe or Lars Von Trier), Pitt is the best thing in it. He plays a muscle head moron who practically lives at the gym and gets caught up in an unlikely espionage plot. Pitt’s able to fully poke fun at his image here (this was only a couple years after he played the golden-God Achilles), and play off it nicely with a final scene that is still shocking. Although he was nominated for an Oscar in “Button” this same year, I think this is the fresher, more experimental performance.

8. “True Romance”…As a beyond-laidback stoner, Pitt steals a movie that is loaded with scene stealers (Dennis Hopper, James Gandolfini, and Christopher Walken all have memorable parts). Quentin Tarantino also wrote this screenplay, and that was the beginning of a professional relationship–“Romance” came out before Pitt was truly huge–that clearly served both men well (“Inglorious,” “Hollywood”).

7. “The Assassination of Jesse James by the Coward Robert Ford”…Although Casey Affleck was deservedly nominated for Best Supporting Actor as Robert Ford (it’s a spooky, career best-performance as a parasitic fan, unlike anything Affleck has ever done), I wish the Academy could’ve also given a nod to Pitt’s work as the larger-than-life outlaw. Like Jesse James, Pitt is from Missouri, and you can feel slight shadings of the actor’s real life bleeding into his portrayal of James, although he basically portrays Jesse as a psychopath (or maybe someone just pretending to be in order to intimidate people into staying loyal). It builds on the early promise of “Kalifornication” and “12 Monkeys,” and is my favorite of Pitt’s unhinged performances. Unless you count…

6. “Fight Club”…For many years, Tyler Durden was probably Pitt’s most famous character. It’s a near-perfect marriage of his charismatic smooth dudes and the nuttier villains he played in “James,” “Monkeys,” and “Kali.” Tyler is an ambiguous character for most of the movie–even when the “mystery” is revealed, we still have more questions than answers–and Pitt’s cypher-cool with a hint of nastiness serves him perfectly. If it weren’t for some of Pitt’s stellar recent work (all of my top 5 are from the last ten years), this would easily be the best.

5. “Once Upon a Time in Hollywood”…Confident from the first scene to his devastating final shot (a callback to “The Searchers,” with his rough stuntman locked out of the more promising, peaceful future that’s in store for DiCaprio’s character), this is an actor at the height of his powers. There’s a very good reason (or ten) that Pitt won his only acting Oscar for this role, and Cliff Booth is a little bit like Tyler Durden, Aldo Raine, Billy Beane (an aging pro worried his best days are behind him), and Rusty Ryan all rolled into one.

4. “Moneyball”…To me, it’s odd that Pitt almost never plays fathers. [It’s only truly central to his characters in this, “Tree of Life,” “Babel,” and “World War Z.”] His vulnerability in the scenes with his daughter make this performance–for me–slightly more affecting than his work in “Hollywood,” and really elevates the entire movie. It gives a deeper angle to a film about people that have been counted out for various reasons, and it’s always more emotional if an anxious character has someone counting on their success. Out of the Pitt performances that have actually been nominated for Oscars, this is my favorite by a nose. Although it was a different 2011 movie–“Tree of Life”–that ties for my favorite performance ever.

3. “Killing Them Softly”…This is probably an odd choice to most people as this is one of Pitt’s biggest commercial flops, but is actually a damn good movie. Pitt plays a hitman for the Irish mob trying to figure out exactly who’s responsible for the robbery of a mob-protected card game. It’s a gritty, ultra-realistic look at modern organized crime (gone are the omnipotent, organized crime bosses of the 50’s, these are low life hustlers and killers scrambling against each other for scraps), and Pitt’s shark is right at the center of it. One of my favorite crime films of all time is “The Friends of Eddie Coyle,” and this is as close as I’ve seen to a modern equivalent. Pitt’s closing speech to Richard Jenkins’s mob attorney about the true nature of America and “business relationships” is both hilarious, ruthless, and completely true.

I’m torn about number 1, so I’m going to declare a tie. And in a way, these performances compliment each other, fully showcasing Pitt’s range…

“Tree of Life”…In what is probably the last great movie Terrence Malick will ever make (this is right before he started overdosing on his own disjointed, ponderous style), Pitt plays not just a blowhard, stern father but an allegory for nature itself; Jessica Chastain’s soft, angelic mother is a stand-in for nurture. While most of the characters struggle to become more than breathing symbols for Malick’s themes, Pitt somehow makes the battle between nature and nurture deeply personal. This is a true, flesh and blood character that–if I’m being honest–reminds me more than a little bit of my own father. Pitt may be playing a man who’s paranoid (it seems the universe is conspiring to prevent his ultimate success), authoritarian, and full of rage, but he also makes “Father” anxiety-riddled, heartbreaking, and tragic. It’s a memorable, fully lived-in portrayal that is unlike anything else Pitt has done.

“Ad Astra”…Whereas he plays an overbearing father in “Tree of Life,” here he plays the son of a complex father figure just to give you an example of Pitt’s range and agelessness (his son in “Astra” comes nearly a decade after he played the father). This is one of the most difficult performances you could possibly pull off as Pitt is asked to play emotionally repressed, but also charismatic yet vulnerable, physically brave yet emotionally scared (at the prospect of seeing his domineering father and his large shadow again), uncertain yet determined. This is all emotionally tricky terrain that would’ve swamped a less skilled actor; too often, actors play compartmentalization as aloof or shutdown, like Ryan Gosling in “First Man,” but Pitt never fails to let just the right amount of emotion bubble up to the surface. [When Tommy Lee Jones tells him that he never thought about Pitt the second he left him, a single tear rolls down Pitt’s face, and he says “I know dad” in a way that’s devastating.] And to do everything I’ve described here in zero-G’s and CGI backgrounds while occasionally wearing a heavy space suit, well…there’s a reason this man has been a star for nearly my entire life.

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