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Once Upon a Time in Hollywood star Brad Pitt’s 6 most unsung performances


Brad Pitt has, for the past three decades, maintained his status as a bonafide Hollywood A-lister. His roles in films such as Fight Club, World War Z and the Ocean’s series have made him more than a household name; he is known by all, from the sleepy suburbs to isolated mountain villages and everywhere in between.

His role in auteur Quentin Tarantino’s next film, Once Upon a Time in Hollywood, is sure to be another hugely popular one, with critical plaudits already echoing from the Cannes Film Festival. He plays stuntman Cliff Booth, who along with his acting counterpart Rick Dalton (Leonard DiCaprio) must navigate the changing landscape of Tinseltown in 1969.

Critics have already lauded Pitt and DiCaprio’s chemistry: “One’s allegiance to the film is consistently won back by DiCaprio and Pitt, who make easy, and disarmingly humble, platonic poetry out of this curious dynamic," Vanity Fair’s Richard Lawson writes.

But we’re not here to talk about the well-known roles – instead, here are six of Pitt’s unsung performances that demonstrate his versatility and acting prowess.

Leonardo DiCaprio and Brad Pitt on Once Upon a Time in Hollywood poster

1. Floyd – True Romance (1993)

Hollywood heartthrob Brad Pitt as a greasy, slobbish, stoner? Oh, absolutely. His role in Tony Scott’s True Romance (scripted by Tarantino) may be a minor one, but he makes quite the impression. Practically fused to the sofa, and always with a herbal cigarette in hand, Pitt is the friendliest, most laid back person you could ever hope to meet... even when obliviously sharing the company of violent, homicidal gangsters in some of the film's funniest moments.

Always happy to kick back with a few beers or a smoke (even if you’re clearly one of the previously mentioned gangsters), Brad Pitt’s loveable layabout has been so influential he even went on to inspire Judd Apatow and the stoner comedy Pineapple Express.

2. Jeffrey Goines – Twelve Monkeys (1995)

For director Terry Gilliam’s post-apocalyptic, time-travelling masterpiece Twelve Monkeys, Pitt showed audiences a side of himself they hadn’t seen before – and it is quite the sight.

As activist and potential terrorist Jeffrey Goines, Pitt fills the screen with an intoxicating maniacal energy, twitching and writhing as he waxes philosophical about the state of the world. With one eye never quite hitting centre, a visual representation of his crooked mind, Pitt is equal parts hilarious and terrifying as his vast intelligence dwells behind his obvious insanity.

Pitt’s performance is morbidly magnetic, and far and away from the usual floppy haired leading man roles you are accustomed to seeing. The role got him his first Oscar nomination but deserves a lot more recognition.

3. Richard – Babel (2006) 

Babel, from director Alejandro González Iñárritu, is a story of tragedy, weaving the intersecting stories of four different families across the globe. After his wife is badly hurt whilst in Morocco, Brad Pitt’s Richard is at a loss as he attempts to save her within increasingly difficult circumstances.

It’s a very different role for Pitt – that of the helpless everyman, his gaunt, scruffy appearance, as well as his inability to save the day with a gun or a master plan, a far cry from the be-muscled heroes audiences are so used to seeing.

4. Jesse James – The Assassination of Jesse James by the Coward Robert Ford (2007) 

Director Andrew Dominik’s cumbersomely titled The Assassination of Jesse James by the Coward Robert Ford casts an intoxicating spell, and Pitt’s central performance is a huge part of that.

A melancholy western, detailing the last years of the infamous outlaw and his relationship with proto-fanboy Robert Ford (Casey Affleck), the film is an expertly crafted, meditative biography. As the titular James, Pitt is every bit the legendary icon, able to make people follow him into certain death as they bask in his confidence, whilst also frightening them with his erratic, violent behaviour and obvious death wish.

Pitt’s performance is both nuanced and measured, displaying James’s inner turmoil and vulnerability with nothing more than a wistful look or contemplative gaze. This is Pitt on award-worthy form.

5. Chad Feldheimer – Burn After Reading (2008)

Pitt has carved out something of a niche in playing loveable dopes, with Burn After Reading’s Chad Feldheimer being his magnum opus. With his quaffed, highlighted hair, incredible dance moves and subpar IQ, Pitt is the naive puppy dog at the centre of the Coen brothers’ comedy crime caper.

Every scene with Pitt is hilarious, from his overly enthusiastic workouts to his laughably inane attempts at scheming and blackmail; he fills the screen with laughter and joy right up until the moment he is unceremoniously taken out of the picture.

6. Benjamin Button – The Curious Case of Benjamin Button (2008) 

The Curious Case of Benjamin Button was largely dismissed as an awards-baiting curio on release (it was nominated for several Oscars), and because of that Brad Pitt’s multifaceted performance went largely unsung. Portraying a character from birth ‘til death, but in reverse, Pitt is of course aided by spectacular special effects, but it is the actor that makes the character so endearing.

Whether playing an old man with a child’s mind or an adult in a young man’s body, Pitt convincingly portrays every stage of this man’s peculiar life, able to display the innocence of the former and the maturity of the latter with natural, believable ease. Forget your action heroes and confidence tricksters, this is Pitt at the top of his game.

Once Upon a Time in Hollywood is released on 14th August, so tweet us @Cineworld if you think Brad Pitt will deliver one of his most memorable performances.

And don't forget that's not the only dose of Pitt we're getting this year: he also stars in sci-fi drama Ad Astra, due for release on 18th September.

Jon Fuge is a writer who blogs for Cineworld as part of our news team.