Our 12 Favourite Brad Pitt Performances

To celebrate the release of Bullet Train in cinemas we are shining a spotlight on our favourite Hollywood hunk, and exceptional on-screen eater, Brad Pitt. A genuine movie star and leading man, though often a scene-stealer in his supporting roles, the charismatic and versatile performer has long been working with the best filmmakers in the business and has been turning in consistent high quality performances.

Through his production company, Plan B Entertainment, Pitt has also produced a number of Academy Award-winning titles including The Departed, 12 Years a Slave and Moonlight. Other acclaimed titles include The Tree of Life, Moneyball, The Big Short, The Assassination of Jesse James by the Coward Robert Ford – all of which he starred in and ‘may’ appear on this list.

Check out this video we put together of our favourite Pitt performances so far and read on for some brief thoughts on each of these roles. Anyone familiar with his extensive career would know that there were some tough decisions to make here.

These are not officially in any order and notable roles that just missed the cut included Ocean’s Eleven, Snatch, Inglourious Basterds, Spy Game and The Curious Case of Benjamin Button.

Mr O’Brien – The Tree of Life (2011)

This (and Moneyball, released the same year) was the start of the baby-faced Pitt’s transition into being able to convincingly play a dad, and what a powerful and complex portrayal of fatherhood is on display in Terrence Malick’s magnificent Tree of Life. This is an unusually structured film, made up of a kaleidoscope of evolutionary ‘moments’ and life snapshots – from an extraordinary cosmic creation sequence involving the Big Bang, to Pitt’s Mr. O’Brien reacting to human creation as he holds the tiny foot of his newborn son. It doesn’t feature a lot of dialogue, but Pitt has an enormous impact through his physicality, portraying a strict, hard-working father who commands respect as he tries to build the the perfect life for his wife (played by Jessica Chastain) and sons.

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Roy McBride – Ad Astra (2019)

The body-altering effect of a person’s bond with their parent/s is at the core of this breathtaking and cerebral sci-fi film from director James Gray (The Lost City of Z). Pitt plays a highly-trained and emotionally-controlled astronaut – it is one of his most understated, yet detailed stoic performances – who evolves as a man, and rediscovers his humanness, as he embarks on a thrilling and perilous journey into the far reaches of space in search of his missing father (Tommy Lee Jones).

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Billy Beane – Moneyball (2011)

Pitt received an Oscar nomination for his work as Billy Beane, the trailblazing general manager of the Oakland A’s whose philosophies transformed the way that baseball players were analyzed and how teams were built under salary cap restrictions. Moneyball is an account of the A’s 2002 season. This is an engaging and uplifting sports story that features very little baseball, but spends its time in Beane’s ‘office’ – his car, the tunnels in the bowels of their home stadium and stuffy meeting rooms where he preaches his strategies to the cynical old-heads of the game. Though perhaps most memorable for the memes of Pitt flipping tables and the playful camaraderie with Jonah Hill’s character, Peter Brand, this is a transcendent sports drama because of Pitt’s likeability.

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Cliff Booth – Once Upon a Time…in Hollywood (2019)

In Hollywood Pitt re-united with Quentin Tarantino (see also Inglourious Basterds) and stars (for the first time) alongside fellow generational movie star royalty in Leo Di Caprio. Just as Pitt was the hotshot up-and-comer in the early 90s, Leo took over the mantle at the turn of the 21st Century. Here they play best buds in an Old Hollywood romanticism story. Pitt plays, with an effortless laid-back charm that should be bottled and preserved, a character who has committed to remaining in the shadow of big personality guys like Leo (here serving as his stunt double), somewhat mirroring his own career. It was Pitt’s performance that the world recognised however, earning him his first Academy Award for Best Supporting Actor.

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Tyler Durden – Fight Club (1999)

If Pitt wasn’t already a household name at this point then this immortal role in David Fincher’s now-cult classic Fight Club would bring this notoriety. Everything that Pitt was renowned for – cheeky, tough-as-nails and with endless sex appeal – was at the centre of this magnetic, incendiary role in a violent and controversial film. While Fight Club’s troubling representation of contemporary manhood became the focus of a lot of analyses, and Pitt’s co-star Ed Norton (American History X) received the bulk of the acting acclaim, Pitt’s incredible performance remains one of his most definitive and formative to this day.

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Donald “Wardaddy” Collier – Fury (2014)

Fury is an underrated movie. This brutal war drama focuses on US tank crews in Germany during the final weeks of the European Theatre in World War II. Pitt, who plays the Staff Sergeant of one Sherman tank crew, which they have nicknamed Fury, is surrounded by some terrific performances – including Logan Lerman, Michael Peña, and Shia Labeouf. But, in this leadership role, his fierce commitment to the mission and ensuring the survival of his crew means that Pitt has to become perhaps the most intense (and unlikeable) he has ever been. David Ayers’ finest work (to date) is truly edge-of-your-seat stuff for most of the running time, accompanied by a spectacular musical score by Steven Price.

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Jeffrey Goines – 12 Monkeys (1995)

Pitt’s first awards attention came in Terry Gilliam’s mind-bending sci-fi (inspired by a terrific short film by Chris Marker, La Jetee), in which he won the Golden Globe and was nominated for the Oscar in the Best Supporting Actor category. Bruce Willis headlines the film, recruited for a mission in the year 2035 to be sent back to the 1990s and gather information about a virulent plague that is set to exterminate the majority of the world’s population. It is in this timeline that he meets Pitt’s Goines at a mental hospital. He has strong anti-corporate activist views, but could he be involved with the outbreak? Pitt, despite being relatively unknown at his time of casting, proved to be a big drawcard when the film was eventually released, due to his rise to the A-list following the release of…

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Detective David Mills – Se7en (1995)

David Fincher’s classic ’90s crime thriller – maybe even the best? – is a stress test of the highest order. Pitt plays a hot-shot detective who finds himself paired with a ‘one-foot-out-the-door’ veteran, Sommerset (Morgan Freeman), in a gruesome hunt for a serial killer whose craft is based on the seven deadly sins. Pitt’s Mills is a new-to-town upstart who initially clashes with Sommerset’s methodical processes, but as their camaraderie develops and the stakes get higher Mills comes into his own. A brilliant lived-in performance that is punctuated not just by the shocking conclusion, but also by an insane foot chase in the middle of the film which sees Pitt throwing himself out of windows in pursuit of a suspect. I’ll always admire Pitt’s commitment to this role.

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

Andrew Dominik’s epic and gorgeously photographed revisionist Western is an intriguing study of one of the legendary outlaws of American lore, whose relationship with his eventual killer Robert Ford (portrayed in stunning fashion by Casey Affleck) is dramatized in this fascinating character study. Pitt naturally assumes James’ appearance and celebrity allure – a figure he was likely drawn to – while the actions of his gang have been romanticised over the years. James’ actions aren’t celebrated or justified here, just presented, but his death is made to feel like a tragedy in this really unique film. Pitt and Dominik would work together again in…

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Jackie Cogan – Killing Them Softly (2012)

While this stylish crime thriller wasn’t to everyone’s taste – it’s depiction of America’s very-recent financial crisis, a modern twist on the 1974 source material, lacked subtlety – this is a witty, visceral and high-impact film. Pitt stars as Jackie Cogan, a renowned leather-clad hitman-for-hire brought in to track down the small time crooks (including Aussie Ben Mendelsohn) who robbed a Mob-protected gambling operation and set in place a chain of events that would cripple the local criminal economy. The film also stars the late James Gandolfini, in one of his final roles.

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J.D. – Thelma & Louise (1991)

Ridley’s Scott’s culturally iconic female buddy road movie is a showcase of the brilliant talents of leads Susan Sarandon and Geena Davis, whose characters are forced on the run from authorities after they kill a man in self defense. Pitt, who plays J.D, a young drifter whom the fugitives encounter and who Davis’ Thelma falls for, is in the movie for a total of 7 minutes. But, the impact would be enormous. Approaching the role ego-free – Pitt declares he was lucky to have been given the role – he took it upon himself to create a unique and memorable character, an approach that would serve him well as he started to gather attention in Hollywood.

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Chad Feldheimer – Burn After Reading (2008)

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When a disc containing mysterious information ends up in the hands of a gym employee, Linda (Frances McDormand), she is convinced by her colleague Chad (Pitt) to try and sell it back to the CIA agent (John Malkovich) responsible for the loss. This sets in motion a series of unfortunate and hilarious events that threaten national security. Pitt is absolutely ridiculous in this outlandish role as a full tilt personal trainer, as is the entire A-list cast who wholeheartedly embrace the absurdist and subversive humour that the Coen Brothers are renowned for. It’s very funny to watch Pitt and George Clooney – who starred as master thieves in the Oceans series – as “dueling idiots” in this bizarre black comedy.