14. “Johnny Suede” (1991)
Though he first really turned heads just a few months earlier in Ridley Scott’s “Thelma & Louise,” Pitt really proved that he had the right leading-man stuff in Tom DiCillo’s indie “Johnny Suede.” The future star plays the title role, a would-be rockabilly sensation with a giant quiff who finds a pair of black suede shoes that seemingly completes his persona, and romances a pair of women (Alison Moir and Catherine Keener). It’s quirky stuff, equal parts Jim Jarmusch and David Lynch, and if it’s possibly a little too in thrall of its influences, it repackages them into something that feels genuinely fresh. Suede himself is a little bit of a blank, deliberately so, but it was the perfect role for Pitt to break out with: his poise and quiet charisma seem torn from the matinee-idol pages of a ’50s magazine. That said, DiCillo didn’t find the experience of making the movie to be an entirely joyful one: its making was reflected in his follow-up, the entertaining “Living In Oblivion,” with James LeGros as Chad Palomino, a part widely believed to be based on Pitt (something that the director has denied).
13. “Burn After Reading” (2008)
Given his love for A-list auteur directors and quirky character roles he can disappear into, it’s sort of surprising that it took Brad Pitt so long to work with the Coen Brothers, and that he’s only done it this one time. Actually, there were other plans beforehand: he was set to star in a near-silent adaptation of “Deliverance” author James Dickey’s WW2 novel “To The White Sea” written and directed by the Coens in the early ’00s, but studios never greenlit the expensive project. It’s a shame that that, or other team-ups, haven’t happened yet, because Pitt is fantastic in “Burn After Reading.” The Washington-set farce disappointed many as the follow-up to the Coens’ “No Country For Old Men,” but it’s aged quite well, seemingly eerily prescient of the current James Comey-era mess we have going on. And among a stellar cast (George Clooney, Frances McDormand, John Malkovich, Tilda Swinton), Pitt steals the show as a thick-as-pigshit gym trainer who ill-advisedly attempts to commit treason.
12. “Inglourious Basterds” (2009)
As is the case with most of the movies Quentin Tarantino’s made in the second half of his career, “Inglourious Basterds” is something of an undisciplined mess. It can be bloated, juvenile and unsatisfying, often substituting sheer volume of material for quality. But when it works, it has some of the best material of Tarantino’s career, from that breathlessly tense opening scene to the extended bar sequence, to the awesome “Cat People” needle-drop as Shoshanna puts on her war paint. Disappointingly few of those best bits actually include the titular squad of Nazi-hunters and their leader, Lt. Aldo Raine (Pitt), who gets essentially a couple of good monologues, and not in Pitt’s best performance at that. But he’s at least been put to good use in recent times for Nazi-bashing memes on Twitter, and that Tarantino squanders his character doesn’t dampen how good so much of the rest of the movie around him is, at least on a scene-by-scene basis.
11. “Killing Them Softly” (2012)
Andrew Dominik and Brad Pitt’s reteam after “The Assassination Of Jesse James By The Coward Robert Ford” was a disappointment to many, and it’s easy to see why: it’s a difficult, spiky, angry little movie, and blunt and over-literal in its political message certainly. But we love the living hell out of it. Adapted from George V. Higgins’ novel “Cogan’s Trade,” it follows the aftermath of a heist pulled by two low-life junkies (Scoot McNairy and Ben Mendelsohn) on an illegal poker game, a job that the Mob want recriminations for, and have hired Jackie Cogan (Pitt) to carry out. Reminiscent of almost nihilistically downbeat ’70s crime fare like “The Friends Of Eddie Coyle” (also based on a book by Higgins), it never seeks to be a crowd-pleaser in the Tarantino-ish manner that its premise might suggest, but is out for something harder: a full-on indictment of the American dream and capitalism, as shown by Pitt’s final, searing monologue. It’s a pleasingly unshowy performance by the star, his hitman ultra-competent and menacing until he finally explodes with this burst of self-justification.
10. “True Romance” (1993)
Pitt’s first encounter with Quentin Tarantino’s work came with his semi-cameo in “True Romance,” a breakthrough script by the future “Pulp Fiction” helmer directed by Tony Scott. Pitt’s role is a tiny one, and mostly inconsequential to some extent: he plays the Rasta-hatted, deeply stoned roommate of Michael Rapaport’s Floyd, a man interested only, it seems, in weed and making sure he gets some cleaning products, a sort-of innocent who unknowingly ends up helping both sides. But it’s still a delightful turn even among the film’s killer ensemble (Christian Slater, Patricia Arquette, Dennis Hopper, Christopher Walken, James Gandolfini, Gary Oldman et al), displaying the comic timing that Pitt doesn’t get to showcase too often. And the film itself remains one of the very best Tarantino-derived pictures: a very modern take on the lovers-on-the-lam genre, full of texture and character.
9. “Ocean’s Eleven” (2001)
Making “Ocean’s Eleven” as good as it was feels like a mind-boggling task now. Not only did Steven Soderbergh have to assemble an all-star cast that could match up with the Rat Pack original — here, George Clooney, Matt Damon, Don Cheadle, Elliott Gould, Bernie Mac, Pitt and Julia Roberts, among others — but he also had to, with writer Ted Griffin, cook up an ingenious heist that could wow modern audiences while giving his cast all a chance to shine, and he had to make the whole trick look effortless too. Fortunately, Soderbergh did all that with a clever, stylish, surprising heist movie that’s never anything but a joy to watch. The whole cast are palpably having a blast, and Pitt’s among them: freed up from carrying the movie, with Clooney’s Danny Ocean in charge, he gets to walk the line between movie-star cool and the character quirks he likes to do the best, and he has great chemistry with basically everyone he shares the screen with.
8. “12 Monkeys” (1995)
Perhaps surprisingly for one of our biggest stars, Brad Pitt’s only been nominated for three acting Oscars (with another two, plus a win, as a producer, for “Moneyball,” “The Big Short” and “12 Years A Slave” respectively). His first nod came for his supporting turn in Terry Gilliam’s brilliant sci-fi picture. A remake of Chris Marker’s short “La Jetée” that proves shockingly effective, it’s centered on a quiet, excellent turn by Bruce Willis as a convict in a virus-ravaged future who’s sent back in time to prevent the spread of the plague that nearly wiped out humanity. But Pitt steals the film from underneath him as Jeffrey Goines, the bad-haircutted asylum inmate (and son of Christopher Plummer’s virologist) who might well turn out to be the animal activist who released the disease. He turns out to be a red herring, but it doesn’t lessen the skill of Pitt’s turn: it comes close to the trap of playing crazy first and foremost, but Pitt’s twitchiness and itchiness just steps on the right side of that, with a dark humor that feels perfectly in sync with Gilliam’s vision.