Be the Shark: Brad Pitt's 10 Best Performances
Brad Pitt has been electrifying the screen for over three decades, appearing uncredited in a handful of films before landing his first leading role at the age of 27 in The Dark Side of the Sun, a 1988 film about one man’s search for a cure to a rare skin disease that remained shelved for almost a decade. He’s an actor who quickly proved to Hollywood that he wasn’t just a pair of beguiling blue eyes and a perfect jaw-line, eventually starring alongside Craig Sheffer in the Robert Redford helmed, A River Runs Through It; an intimate portrayal of brotherhood spanning the years between World War I and the Great Depression that garnered the young star critical attention. It’s a performance that separated Pitt from the youthful irresistibility that began to define him after seducing his way into a bag of money in Thelma & Louise, showcasing the capabilities of an actor who would go on to become one of Hollywood’s greatest stars.
With the Blu-ray and 4K release of Ad Astra – out today, about an astronaut journeying into the heart of darkness in search of his father - and Once Upon a Time…in Hollywood - Quentin Tarantino’s 9th feature film about a washed-up Hollywood star, his stunt-double and the young actress their paths intertwine with – I take a look at the actor’s best roles that helped define a career spanning nearly 60 films. From a Bakshi transplant to a time-bomb of fragile masculinity, all the way to an ill-fated personal trainer in way over his head, these are the ten best performances that make up the age-defying career of Brad Pitt.
10. Frank Harris, Cool World
Before being rushed off to Cool World, a fetishized world of animated debauchery from the mind of Ralph Bakshi (Wizards), we’re introduced to World War II soldier Frank Harris (Brad Pitt), whose return home is cut short when a drunk driver kills his mother after nearly careening into their motorcycle. It’s a brief moment of heart-shattering gravity-fueled by PTSD - in a film that’s filled with booze-fueled toons that inhabit a world that acts as a respite from the pain and plunder of reality. For much of Cool World, Pitt is drifting through animation that feels as alive as his hair, but for these few moments, the young star showcases a range that far exceeds just another pretty face.
9. Jeffrey Goines, 12 Monkeys
In the broken future of an apocalyptic wasteland now ruled by wildlife, where humanity has sunken to the bowels of civilization in order to survive a plague torn world, a test subject named James Cole (Bruce Willis) must navigate the past in order to save the future. It’s here where he meets Jeffrey (Brad Pitt), a manic mental patient and future anarchist – a theme Pitt will adopt four years later in Fight Club – who steals every drop of screen-time from the actor. Sinking deep into a character that could have been a throw away role in the hands of a less magnetic screw, Pitt manages to achieve the grand watermark of being the weirdest piece to 12 Monkeys entire assembly, an accomplishment that not even director Terry Gilliam’s visionary sense of surrealist wackiness can overcome.
8. Floyd, True Romance
If Tony Scott’s odyssey into uncut coke and untapped male aggression is anything but, it’s subtle. Based off a screenplay by a young Quentin Tarantino, True Romance exhilaratingly and exhaustingly follows Clarence Worley (Christian Slater), a live wire with a short fuse and long itinerary of red flags who hits the road to LA after falling for a call-girl named Alabama (Patricia Arquette). Along the way, a cracker-jack box of unhinged characters become entangled in Clarence’s threaded web of the American dream, though none as unceremonious and unapologetically sublime than Floyd; a tangled mess of weed and Funyuns who spends the entirety of the film on a couch smoking from a homemade Honey Bear bong. While he makes up not even 5 minutes of the films nearly 2-hour runtime, its Pitt’s tenacity for Floyd’s resin-coated lifestyle that feels indebted to the Spicoli bravado of Fast Times at Ridgemont High while remaining unmistakably distinct.
7. Mickey O’Neil, Snatch
British director Guy Ritchie has a tendency to create crime sagas with plots as tangled and cryptic as his characters accents. In Snatch, the follow-up to 1998’s similarly cocked Lock, Stock, and Two Smoking Barrels, Ritchie plays up the indecipherable nature of his crooks with dialogue that nearly demands closed-captioning. Taking this to the extreme is Brad Pitt’s performance as Mickey, an Irish gypsy with a fast mouth and an even faster right hook who must descend into London’s underground bare-knuckle boxing league after sending one of their fighters to the hospital set to a magnificent use of The Strangler’s ‘Golden Brown’. It’s a role that manages to go toe to toe with an over-indulgent cast – Jason Statham, Benecio Del Toro, Dennis Farina, Stephen Graham, Vinnie Jones, Lennie James, Jason Flemyng, to name a few – while showing an actor chew scenery with an accent that makes the slang in Attack the Block sound like an ESL course.
6. Tyler Durden, Fight Club
If you told me that the angelically handsome and clean-cut star of Meet Joe Black would become the iron-ab’d anarcho of David Fincher’s satirical Fight Club – an adaptation of Chuck Palahniuks 1996 book that’s more of a masculine wake-up call than a rally cry - I probably would have thought nothing of it. Except Tyler Durden, consuming the life of a John Doe (Edward Norton) whose IKEA constructed white collar existence hits life’s unsympathetic rock bottom, is essentially an unwavering time-bomb that is solely meant for Brad Pitt. His beautiful, polished features are hardened and given an agenda, creating a bleeding heart of testosterone that manages to tick with uncertainty. It’s a character whose sole existence rests on an actor’s ability to transform an idea into a symbol, and despite becoming an icon for the angry milquetoast of America, Pitt manages to infuse Durden with more toxic complexity than your average adrift misogynist can handle.
5. Chad Feldheimer, Burn After Reading
Brad Pitt once said, “By nature, I keep moving man. My theory is, be the shark. You’ve just got to keep moving. You can’t stop”, and by every measure, he hasn’t. In cinema’s vast ocean, Pitt has chased horror (Cutting Class), sweeping romance (Legends of the Fall) and action (Mr. and Mrs. Smith), yet it’s comedy that seems to get the most mileage out of this momentum. In Burn After Reading, the Coen Brother’s politics skewering mystery that happens to feature a sex chair, Pitt plays Chad Feldheimer, a hapless personal trainer who becomes embroiled in a ransom scheme after discovering a cache of classified documents in a gym locker room. What unravels is Pitt at his funniest, playing a clueless fitness fanatic with as much charm as there is thick-headed gullibility. This isn’t an actor playing a character but becoming them, losing themselves behind a décor of doltish eccentricity that never loses steam until the very startling and tragic end.
4. Don “Wardaddy” Collier, Fury
In the outcome that the American Jewish death squad of Inglorious Basterds wound up on the wrong end of a Panzerfaust, I’d like to think that Brad Pitt’s raspy Nazi hunter Lt. A-L-D-O Raines would find his way into the bowels of a rugged tank and become the unrelenting father figure to a rag tag team of WWII soldiers. Except behind the somehow impermeable hair and jagged scar of Raines is Don “Wardaddy” Collier, a man tormented by war and the unyielding sense of failure who leads his men into almost certain death. While Pitt is no stranger to commanding looks, it’s here where he taps into the anguish and despair of wars vast landscape of hopelessness. Of the toll it takes trying to be someone as impenetrable as a tank. When Wardaddy breaks down in front of a handful of quarantined prisoners, their gaze as empty as the fields that surround them, we can’t help but feel the crushing weight of a war as encompassing as Pitt’s emphatically blue eyes.
3. Jesse James, The Assassination of Jesse James by the Coward Robert Ford
Before playing director Andrew Dominik’s hitman in 2012’s far less subtle Killing Them Softly, Brad Pitt played the titular Jesse James in The Assassination of Jesse James by the Coward Robert Ford, a hopelessly sincere western about the feared outlaw and his fatal relationship with Robert Ford. Similar to another entry on this list (see #3), The Assassination of… is a film that relies heavily on the lingering gaze of its actors, and what Pitt weaves through brooding and long looks is nothing short of masterful. For much of its deliberately paced, nearly 3-hour runtime, Dominik’s film moves from scenes of breathless beauty – Roger Deakins eye never wasting an inch of its canvas – to Pitt’s piercingly grim gaze that manages to be as long as the film’s title. What The Assassination of… proves is just how striking and emphatic of an actor Pitt has become, relying less on the relentless power of his physique and more on the complex struggle between light and dark, good and evil. He’s an actor who manages to channel the futility of stardom, of what it means to be obsessed on and picked over until there’s nothing left, turning it into a brooding masterclass of despair; on what it means to accept deaths hand down the barrel of a loaded gun.
2. Major Roy McBride, Ad Astra
In director James Gray’s sprawling yet intimate sci-fi tale, a son (played by Brad Pitt) must venture into deep space in order to confront his father (Tommy Lee Jones), who has been missing for 16 years after a failed mission to Neptune. It’s a film that deeply conveys the innate dangers of space travel set in a not too distant future, where colonization on the moon has already happened, while shaping the nature of how we perceive and handle our own depression. Pitt wears the emotional baggage of Roy’s bottled intimacy issues like heavily drawn curtains eclipsing a cluttered room. There’s a magnitude to the actor’s eyes that feel worn down by the weight of his character’s emotional reservation, as well as Pitt’s own journey through the open lens of his public life. Much of Ad Astra’s dialogue comes through in voice-over that relays the psychological struggle into outer space, yet the unspoken conversation Pitt’s face speaks says so much more about what it means to feel adrift in the expansive trek through depressions vacuous black hole. This is a film that deeply searches for meaning in existence, on embracing the life we can feel through our own time and space, and in doing so gives us a performance from an aged actor that’s as breathlessly sweeping as the galaxy Ad Astra depicts.
1. Cliff Booth, Once Upon a Time… In Hollywood
If The Irishman, Martin Scorsese’s most recent epic about Jimmy Hoffa (Al Pacino) and his long-time associate and hitman Frank Sheeran (Robert Deniro), is a heartbreaking summation on one of Hollywood’s eldest (and most masterful) directors, then Quentin Tarantino’s 9th film is the mid-life parallel to a seasoned actors career. In Once Upon a Time…in Hollywood, Brad Pitt plays professionally strained Cliff Booth, a middle-aged stunt-man whose career during the peak of 1960’s Hollywood is spent looking over the edge and lugging around actor Rick Dalton (Leonardo DiCaprio), whose trajectory is pinned firmly between the bottle and an hour-glass. Similar to The Irishman, an ambitious 3 ½ hour character study that sees Frank reflecting back on a blood-splattered past, Once Upon a Time… partly focuses its sun-flecked saga on Cliff, who cerebrates on his life spent as a stunt-man and a shadow to long-time friend Rick. Pitt, who will be turning 56 later this December, embodies the ruminative charisma of a figure who has navigated Hollywood’s depths, seeming to mine from his past as well as his own demons. Much of Once Upon a Time…’s nearly 3-hour run-time is spent hanging out with its two stars, yet it’s Pitt who feels like he’s dipped his cigarette into an entire career worth of highs and lows, slowly taking drags that showcase an actor pondering life through the embodiment of a career-defining role.
