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Ad Astra star Brad Pitt: from outlaw to astronaut – his most iconic roles

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As acting CVs go, few are as impressive as Brad Pitt’s. His career has spanned over 30 years, including six Academy Award nominations (counting those as both an actor and producer) and a namecheck in a Shania Twain song.

Equally memorable playing a soap-making terrorist as he is sporting the spandex as a dim-witted personal trainer, Pitt’s diverse acting talents have enabled him to avoid being defined by genre. As a result, he’s been able to navigate the vast landscape of cinema, finding critical acclaim in both studio franchises and independent films.

Later this month, the star will, quite literally, be taking to the stars in Ad Astra. Director James Gray’s highly anticipated sci-fi odyssey is the story of an astronaut (Pitt) on a mission to the outer reaches of the solar system in search of his estranged father (Tommy Lee Jones).

With an engrossing story, stunning cinematography from Interstellar's Hoyte van Hoytema and an ethereal score from Max Richter, Ad Astra has all the hallmarks of a soaring sci-fi classic. The movie generated critical acclaim at the Venice Film Festival with many citing Pitt's performance as a career-best.

In anticipation of the film's arrival on 20th September, we’re taking a look at its leading man’s most iconic movie roles so far. Scroll down beneath the poster to find out what they are.

Brad Pitt on Ad Astra movie poster


1. Jeffrey Goines – 12 Monkeys (1995)

Inspired by 1962 French short film La Jetée, 12 Monkeys brings together the talents of Bruce Willis, Madeleine Stowe, Brad Pitt and director Terry Gilliam in a gloriously off-the-wall mash-up of science fiction, neo-noir and time travel.

Pitt plays Jeffrey Goines, a Baltimore mental hospital patient with a set of radical views that, come the film’s final third, might have just manifested into something altogether more alarming.

Pitt’s role is very much a supporting one — it nabbed him an Oscar nomination — but the film is all the more wonderfully chaotic whenever he’s on screen.


2. David Mills – Se7en (1995)

David Fincher’s atmospheric serial killer thriller contains several memorably gruesome episodes, so it’s somewhat ironic that arguably the most impactful moment is a simple four-word question.

Even in the knowledge of what grisly answer awaits Se7en’s rookie cop David Mills, it’s the desperate cries of “What’s in the box?” that stay engrained in the mind.

Pitt’s turn as an idealistic, ambitious but ultimately reckless young detective is the suitably temperamental ying to the yang that is Morgan Freeman’s calculated, soon-to-retire old guard.


3. Tyler Durden – Fight Club (1999)

At the risk of breaking the cardinal rule of David Fincher’s film (adapted from Chuck Palahnuik’s seminal source material), no list of iconic Brad Pitt roles would be complete without talking about Fight Club.

A gritty, playful, stylish slice of postmodern cinema, Fight Club pulls very few of its punches in its assessment of emasculation, violence and consumerism. And swinging hardest is Pitt’s Tyler Durden: a chaotic, charismatic maverick who, via the story’s infamous third act twist, becomes both the narrative’s protagonist and its antagonist.

Pitt imbues the hyper-masculine Durden with a reckless, unhinged charm, unpredictable authority and a killer set of cheese-grater abs.

In something of a neat 1990s companion piece to 12 Monkeys, Pitt’s performance in Fight Club proves he’s just as convincing playing the unhinged anti-hero as he is the suave, endearing heartthrob.


4. Rusty Ryan – the Ocean’s series (2001-2007)

Ensembles don’t come mightier than Steven Soderbergh’s Ocean’s franchise. Across three films (four if you include the 2018 Sandra Bullock spin-off), countless A-listers and one impressive legacy, the series helped reinvigorate the heist movie in the mid-2000s.

Inspired by the 1960 film of the same name starring the famous ‘Rat Pack’ — which included Frank Sinatra —Soderbergh gave the classic caper a contemporary shake-up, creating a series defined by its slick pacing and stylish visuals.

Pitt plays the ingeniously named Rusty Ryan: a seasoned, sharply dressed con man who is anything but rusty. A close confidant to the franchise’s titular, cooler-than-cool crook, Danny Ocean (George Clooney), Rusty’s aptitude for pulling off the perfect crime is matched only by his appetite for a light snack.





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

In the southwestern region of Missouri, you’ll find the city of Springfield. Aside from sharing its name with the town from The Simpsons, it is also the birthplace of Jesse James. And it is also the city where Brad Pitt grew up.

It seems fitting that the actor would play the infamous outlaw in Andrew Dominik’s 2007 revisionist Western, The Assassination of Jesse James by the Coward Robert Ford. An aptly lengthy title, the film is a 160-minute-long, meditative, beautifully shot epic that retells the events leading up to the titular event.

Pitt’s central performance — a nuanced blend of sorrow and self-awareness — perfectly complements Roger Deakins’ mesmerising, melancholic cinematography.


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

In David Fincher's melancholic, decade-spanning epic, Pitt quite literally, gets better with age. His third collaboration with Fincher — a loose adaptation of an F. Scott Fitzgerald short story — the film tells the tale of a man with a unique condition that means he ages in reverse.

A fairytale with shades of Forrest Gump, the film is a touching love story with a twist, with Pitt’s performance as the titular character earning him a Best Actor Oscar nomination.


7. Aldo 'The Apache' Raine – Inglourious Basterds (2009)

Brad Pitt playing a cool, charismatic stuntman in 2019’s Once Upon a Time in Hollywood — Quentin Tarantino’s sun-soaked love letter to 1960s Tinseltown — might not immediately seem all that meta.

But, as die-hard Tarantino fans will know all too well, it’s not the first time Pitt has played — or, in this case, pretended to play — a movie stuntman in a Tarantino film.

For a brief time, he poses as a fictional stunt guy Enzo Gorlami in Tarantino’s revisionist World War II film Inglourious Basterds. For the rest of the film, however, he’s Aldo Raine: the Nazi-murdering leader of a team of American-Jewish soldiers.

In typical Tarantino fashion, Raine is eccentric, unpredictable and apathetically violent. In other words, pretty darn memorable.

Ad Astra is released on 18th September, so check out the trailer and tweet us your favourite Brad Pitt roles @Cineworld.

George Nash is a writer who blogs for Cineworld as part of our news team.