7. “Fight Club” (1999)
He’s made better movies, we’d argue, but Tyler Durden in “Fight Club” is undoubtedly, when all’s said and done, probably Pitt’s most iconic turn, the one that springs to mind first when you think of him. His second team-up with regular collaborator David Fincher (the pair will soon reteam on “World War Z 2”) came on this adaptation of Chuck Palahniuk’s firecracker of a book, about an anonymous cubicle drone (Edward Norton) pulled into a chain of underground fights by a mysterious and charismatic figure (Pitt). We all know the eventual twist by now, and it’s one that makes Pitt’s casting all the more perfect for a film about dulled masculinity and the things that it cooks up: we’d all want our id to look like Pitt, to have his command of a room and his jacket collection. But the actor’s performance gets stronger and stronger as Durden becomes more unhinged, and his shaven-headed flamboyance feels genuinely dangerous in a way that few stars could pull off.
6. “Moneyball” (2011)
Given that it was a multi-Oscar nominated movie (including picking up Pitt’s last nomination to date) that got great reviews and strong box office, it might seem weird to call “Moneyball” underappreciated. But it kind of is: every time we rewatch it (which is more or less every time it’s on TV — it’s one of those movies where you catch five minutes and end up sitting through to the end), it feels like its place as a classic becomes more and more cemented in our minds. The film nearly happened a few years earlier with Steven Soderbergh: when the helmer was fired by the studio, Pitt stayed on board as director Bennett Miller and writer Aaron Sorkin retooled Steve Zaillian’s original take. The result is one of the best sports movies ever, as Pitt’s GM Billy Beane reinvents baseball with the help of a mathematician (Jonah Hill). It’s ferociously smart and deeply entertaining even if you don’t know a thing about the sport, with Miller lending the film a melancholy tinge, and it has maybe Pitt’s best pure movie-star performance (thus finally fulfilling all those early Redford comparisons).
5. “The Tree Of Life” (2011)
Full disclosure: we’re not actually sure that Brad Pitt is all that good in Terrence Malick’s intimate epic “The Tree Of Life.” He’s prone to a certain kind of try-hard, mannered performance sometimes — “Inglourious Basterds” is one example, “War Machine” looks like another — and there’s too much of that in his jutting jaw and Texan drawl in “The Tree Of Life.” But Malick’s films are rarely really about performances, and the film remains an absolute wonder, and one of the best things that Pitt’s ever been in nevertheless. Years in the making, and seemingly at least in part autobiographical for the director, the film sees Jack (Sean Penn) reflect on his childhood, and his relationship with his parents, in a remarkable, eye-meltingly beautiful journey that spans from the beginning of the universe. And for all our reservations about Pitt’s performance in places, he does at least exemplify a certain kind of American fatherhood that makes him perfect for the film.
4. “Thelma & Louise” (1991)
Pitt got his first mainstream exposure in Callie Khouri and Ridley Scott’s marvel of a road movie, playing the small-time thief who hooks up with Thelma (Geena Davis), only to abscond with the life savings of Louise (Susan Sarandon), putting the pair on the path of desperation and criminality that ultimately ends with them taking a dive into the Grand Canyon. And little wonder that the film instantly made Pitt a star: he’s outstandingly, indelibly sexy in it, his Southern drawl seducing with every word. But as memorable as his small role is, he’s hardly the most interesting thing about the film, a moving, fiercely feminist story of freedom that remains one of Scott’s very best films. Davis and Sarandon are both extraordinary, the film entertains as much as it moves, and the ending is one of cinema’s very greatest.
3. “12 Years A Slave” (2013)
It feels a little bit like we’re beating up on Pitt after the last couple of capsules, near the top of the list, to say that he’s somewhat unhelpful to “12 Years A Slave” when he appears on screen as the Canadian carpenter who helps, in his way, to free Solomon Northup. As a producer of the film, it jars a little that he’s given the only entirely sympathetic white role, and his late cameo slightly stops the film in its tracks just because of how deeply recognizable he is. But it’s a good performance all the same, and Pitt still deserves credit for helping to get such an extraordinary movie made in the first place: his attachment as producer and supporting player surely helped a tough sell to get the greenlight. And that’s an absolute good: Steve McQueen’s Oscar-winning drama is a landmark movie, directed with absolute control, performed extraordinarily by Chiwetel Ejiofor, Michael Fassbender, Lupita Nyong’o, Sarah Paulson, Adepero Oduye et al, and at once unwatchably bleak and, in its deliverance at the end, unutterably moving. It may be the definitive movie about slavery, at least for now.
2. “Seven” (1995)
If “Thelma & Louise” made Pitt one to watch, it was “Seven” that made him an A-list movie star. He’d had hits in the interim — “A River Runs Through It” did remarkably well for a movie about fly-fishing, “Interview With The Vampire” was a smash — but those were movies to some extent carried by more established names. “Seven” was an impossibly bleak movie from a director who’s only film to date was a high-profile flop, and yet Pitt and co-star Morgan Freeman, who play cops tracking down a serial killer whose elaborate murders target and recreate the Seven Deadly Sins, helped it to make $100 million domestically. Indeed, it to some extent helped establish the Pitt brand: edgy, auteur-driven pictures that would thrill you, but not necessarily comfort you. Andrew Kevin Walker’s fiendishly clever script didn’t just grip and surprise, it also became a moral fable about the rottenness of the world, a world executed with enormous style and real substance by director David Fincher. And while their buddy-cop dynamic might look familiar, it’s hard to think of two actors who could have given the battle for David Mills’ soul that the ending pivots on more weight than Pitt and Freeman.
1. “The Assassination Of Jesse James By The Coward Robert Ford” (2007)
In a recent interview with GQ Style, Pitt revealed that he considers “The Assassination Of Jesse James By The Coward Robert Ford” the best movie he ever made. And you know what? He’s damn right. Andrew Dominik’s adaptation of Ron Hansen’s novel is an elegaic, poetic Western of the kind that hadn’t really been made since the 1970s, meticulously paced (it’s nearly three hours long), but with every frame justified in part because Roger Deakins does what’s still the best work of his career in it. It sprawls and follows tangents in a novelistic way, but always returns to the central relationship between the legendary outlaw (Pitt) and the man who hero-worshipped him and then went on to kill him (Casey Affleck). You needed a huge star to play James, and Pitt is perfect, but he’s also perfect on a performance level: quiet, steely, deadly, charismatic, regretful, mournful and terrifying. It’s a measure of his generosity as a performer, though, that it’s never the Brad Pitt show: he’s just one cog in an engine that drives a movie that, at least for another few months, is the best film of the last 10 years.
Of the films that didn’t quite make the list, the closest was probably Ridley Scott’s “The Counselor,” hailed by some as a masterpiece, by others a total failure. We’re somewhere in between: the misanthropic crime picture is fascinating, but is mostly in the hands of the wrong cast, and to some extent the wrong director too.
Beyond that, “A River Runs Through It,” “Legends Of The Fall,” “Seven Years In Tibet,” “Sleepers,” “Mr. & Mrs. Smith,” “Megamind” and “The Big Short” all have much to recommend them, but weren’t quite enough to crack the final 20. We also excluded a film where Pitt has tiny cameos, like “Being John Malkovich” and “Confessions Of A Dangerous Mind.” How will “War Machine” fare? You can find out when the movie hits Netflix on Friday.