From hair to eternity: Brad Pitt in 37 films

Brad Pitt – a rough, tough name in the tradition of Rock, Brick or Chip, with maybe just a hint of manly coalmining – is the classic embodiment of the American Dream, a boy from a humble background or even ‘hillbilly country’, who made it big in Los Angeles. “In some ways, I’m still a kid from Missouri and Oklahoma,” he once said.

Once Upon a Time… in Hollywood and Ad Astra are both in UK cinemas.

After paying his dues in bit parts and TV, his breakthrough came in 1991 with a one-two punch of mainstream hit and indie arthouse. His brief role in Thelma & Louise as a hunky young hitchhiker, a cannier Joe Buck in a cowboy hat who knows what women want (but who won’t hesitate to rip them off) is a stripped-to-the-waist calling card.

The artier half of this complementary double was the title role in Tom DiCillo’s Johnny Suede. Pitt, pouting like Cocteau muse Édouard Dermit with added pompadour, plays a hipper-than-thou neo-1950s aspiring rockabilly star who wanders around his New York flat with a hand absent-mindedly tucked down the front of his underpants. Pitt was long rumoured to be the real-life model for the ridiculous method actor Chad Palomino (James LeGros) in DiCillo’s later comedy about low-budget filmmaking Living in Oblivion (1994), but the filmmaker has denied this.

In fact, Pitt himself was slated to play Palomino before he dropped out to take a leading role in Robert Redford’s third film as director, A River Runs Through It (1992). The film is an adaptation of Norman Maclean’s autobiographical memoir about coming of age in picturesque Montana landscapes, with fly-fishing a metaphor for the human condition, and Pitt cast in the sort of role that might once have been filled by the Sundance Kid himself. It established Pitt as Redford’s heir, Hollywood’s new golden boy.

Golden boy rode again in Legends of the Fall (1994) – which might as well have been called ‘Legends of the Hair’, since not even Anthony Hopkins hamming it up as a stroke victim with a speech impediment can distract from Brad’s backlit tresses as he moseys around roping steers, wrestling grizzlies and killing Germans.

He went even blonder for Seven Years in Tibet (1997), in which he plays Austrian ex-Nazi Heinrich Harrer (in real life fêted by Hitler as part of the team that made the first ascent of the north face of the Eiger in 1938), who escapes from a POW camp in 1944 and toils over spectacular Himalayan topography to live among peace-loving Buddhists clad in yak pelts.

The blond turned bland in the misconceived Meet Joe Black (1998), in which Pitt plays an inexplicably unworldly Death, tasting peanut butter for the first time with childlike gormlessness.

But just as there’s some truth in the cliché that every comedian secretly wants to play Hamlet, so the old adage that inside every matinee idol is a character actor itching to get out is not entirely fanciful. Good looks have never been a hindrance to a Hollywood career, but as Alec Baldwin and Matthew McConaughey – to name but two – have shown, it’s not until he’s looking a little ragged around the edges that an actor’s capabilities are taken seriously. Throughout the 1990s, parallel to the films that showcased Pitt’s romantic beauty, he was already making strenuous efforts to undermine his goldenness, expressing his intent to move on from “this ‘pretty boy’ thing… and play someone with flaws”.

And flaws is what we got, with knobs on. He unleashed his inner psycho as Early Grayce, the squinty serial killer on a road trip in Dominic Sena’s Kalifornia (1993), in which he starts off as a redneck deplorable in a Dixie cap and ends somewhere north of Robert Newton ‘oooh-arrgh’ territory, barely able to stop for gas without stabbing or shooting someone.

For True Romance (1993), an early Tarantino screenplay, Pitt reportedly called director Tony Scott to ask for the role of comic relief reefer-smoking Floyd, and then improvised most of his lines.

The results were so convincing that the stoner label continued to dog him for the rest of the decade, at least and not always without reason. “I was hiding out from the celebrity thing,” he would tell the Hollywood Reporter in 2012. “I was smoking way too much dope. I was sitting on the couch and just turning into a doughnut, and I really got irritated with myself.”

His wan performance as one of the bloodsuckers in Neil Jordan’s Interview with the Vampire (1994) was easily overshadowed by his co-stars, though the sight of Tom Cruise hovering lasciviously over Pitt’s jugular did provide one of the more explicit homoerotic images served up by major Hollywood stars in the 1990s.

But Pitt is a perfect hot-headed foil to Morgan Freeman’s calm philosophical investigator in Se7en (1995); Pitt’s character, Detective Mills, looks all set to emerge as a typical action hero, but it’s these same gung-ho qualities that seal his doom as the ultimate fall guy. It was the first of three leading roles for David Fincher.

He is all mannered twitchiness as psychiatric patient Jeffrey Goines in Terry Gilliam’s Twelve Monkeys (1995), a lurch into look-at-me-I’m-acting that earned him critical acclaim, a Golden Globe and an Academy Award nomination for Best Supporting Actor.

In Alan J. Pakula’s The Devil’s Own (1997) he breaks out the Irish accent as an IRA terrorist whose attempt to buy Stinger missiles in NYC goes awry. The film never gets to grips with its mixed messages, but in retrospect the character feels like a dry run for ‘One Punch’ Mickey O’Neil’s mangled brogue in Guy Ritchie’s Snatch (2000), ranked by the Independent as one of the ten worst Irish accents in film history. Ritchie reportedly rewrote the role when Pitt proved unable to master Cockney, but his bare-knuckle boxer is the funniest character in the film, and sports a lean, mean torso (covered in tattoos) in the ring.

The Pitt six-pack was also bared in Fincher’s Fight Club (1999), adapted from the cult novel by Chuck Palahniuk. Tyler Durden is a corrupted version of the golden boy, oozing effortless cool as the definitive lad’s lad in a film that doesn’t seem to be sending up toxic masculinity as much as celebrating it.

Echoes of young Redford are again discernible in Tony Scott’s Spy Game (2001), in which the older actor’s veteran operative has to single-handedly save his former protégé (Pitt) from execution on the far side of the world.

But peak jeunesse dorée is attained in Pitt’s outrageously buff – and frequently in the buff – appearance as Achilles in Troy (2004): shining armour, flowing locks and a nifty trick of leaping in the air to stab his opponents in slow-mo in between heterosexual couplings in tents.

Troy was the first film Pitt helped to produce. He formed Plan B Entertainment in 2001 with Jennifer Aniston and Brad Grey; after his 2005 divorce from Aniston, Grey moved to Paramount Pictures and Pitt became sole owner of the company, bringing in Dede Gardner and Jeremy Kleiner as president and co-president. “Plan B is really a little garage band of three people,” Pitt has said, “and our mandate has been to help get difficult material, that might not otherwise get made, to the screen and to work with directors we respect.”

The company has often obtained properties with a view to Pitt starring in them – he was originally slated for Matt Damon’s role in Martin Scorsese’s The Departed (2006) and Charlie Hunnam’s in James Gray’s The Lost City of Z (2016), both Plan B coproductions – but has also shown impeccable instincts in backing such critically acclaimed films as Selma (2014), Moonlight (2016), Okja (2017), Beautiful Boy (2018) and Vice (2018). Pitt also took supporting roles in 12 Years a Slave (2013) and The Big Short (2015), as well as producing them.

Meanwhile, the actor’s palpable chemistry with wife-to-be Angelina Jolie in the slick contract-killer caper Mr. & Mrs. Smith (2005) embroiled him in tabloid gossip even as he was diligently expanding his range into portentous drama (Alejandro González Iñárritu’s Babel, 2006), screwball comedy (the Coen brothers’ Burn After Reading, 2008, in which, as goofy fitness trainer Chad Feldheimer, Pitt was once again the funniest thing in the film) and romantic whimsy, nabbing a Best Actor Oscar nomination for ageing backwards in Fincher’s The Curious Case of Benjamin Button (2008).

Andrew Dominik’s The Assassination of Jesse James by the Coward Robert Ford (2007), another Plan B production, gave the actor one of his best roles, channelling his natural screen charisma into the incarnation of sociopathic celebrity.

He played another, less glamorous killer in Dominik’s next film, Killing Them Softly (2012), a belated entry in the cool hitman trend, which, like the Jesse James film, underpinned genre thrills with topical subtext.

Another portrait in his ruffian’s gallery is Westray in Ridley Scott’s The Counsellor (2013), a wily fixer with a cowboy hat and greasy ponytail, whose final scene is one of the most shockingly gruesome deaths of an A-list star ever committed to film. “I die really well, by the way,” Pitt has said, in relation to his career in general. “It’s one of my strong points. I just take a bullet well.”

Pitt joined up with George Clooney and director Steven Soderbergh for a taste of franchise success as part of the all-star male ensemble cast of the larky Ocean’s Eleven caper (2001) and its sequels (2004/2007), demonstrating plenty of what has since been recognised as one of his special talents – eating while acting.

Junk food is a recurring motif in the Jerry Maguire-esque Moneyball (2011), landing him another Oscar nomination for delivering lots of motor-mouthed technical sports-related dialogue through a mouthful of munchies.

Pitt also produced Terrence Malick’s The Tree of Life (2010) – in which he plays the protagonist’s authoritarian 1950s father – as well as his grandiloquent Imax documentary Voyage of Time: Life’s Journey (2016).

Another potential franchise reared its rotting head in the Pitt vs zombies movie World War Z (2013), considered by many a betrayal of the oral history source novel by Max Brooks; a sequel was announced but shelved in 2019 due to budget issues.

His segments are the weakest link in the episodic Inglourious Basterds (2009), his first collaboration with Tarantino; Pitt tries hard – too hard – as Nazi-killing US Lieutenant Aldo Raine. He has never been wholly convincing in tough military roles, mostly seeming to act with his chin as the scarred World War II tank commander in David Ayer’s Fury (2014) or failing to win Afghan hearts and minds in the more satirical portrait of American military muscle, David Michôd’s War Machine (2017), another Plan B production.

He seems more at home in the romantic WWII espionage melodrama of Robert Zemeckis’s Allied (2016), his swoony chemistry with Marion Cotillard harking back to Mr. & Mrs. Smith, but with more emotional realism.

In Tarantino’s rambling and uneven Once upon a Time… in Hollywood, the flights and digressions are tethered by the bromance at its heart. Leonardo DiCaprio’s performance as Rick Dalton, an alcoholic TV star on the skids, is a study in tragicomic desperation, but it’s Pitt as his loyal stuntman, driver and odd-job man Cliff Booth, who commands attention.

While DiCaprio keens and perspires to droll effect, Pitt is reined in, watchful and reactive, with hints of something tightly coiled and dangerous just beneath the affable façade. The Pitt torso still looks nicely ripped when he peels off his shirt, but the erstwhile golden boy has acquired interesting wrinkles, both literally and metaphorically, and seems to have absorbed aspects of his earlier stoner and psycho-killer personae, so the results feel less like acting and more like a fully rounded human being who could conceivably exist off the screen as well as on it, where he is equally compelling fending off flocks of dead-eyed hippies as feeding his dog or simply motoring around town. Without resorting to gurning or chin-thrusting ‘character acting’, he hints at Booth’s dark side so economically that Tarantino’s flashbacks to his backstory feel saggy and redundant.

Pitt is at his best when seeming to play himself, Cary Grant-style, and James Gray’s Ad Astra, another Plan B production, plays to his strengths. As Roy McBride, an astronaut whose pulse rate has never risen above 80, his reactions have been so successfully internalised that on the surface he seems emotionless, in control, almost an automaton. His interior monologue, while delivered in a suitably affectless tone, suggests otherwise, but, like Tarantino’s flashbacks, it’s a monologue rendered virtually redundant by Pitt’s face. Ad Astra gives us plenty of time to study it, and it’s the mark of an exceptional performance that the actor is able to convey Roy’s internal turmoil and malaise with minimal effort, largely through his eyes.

Maybe Brad Pitt is not a natural character actor, and shouldn’t try to be one. He’s a star, perhaps the last true film star in Hollywood.