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Six Definitive Films: The ultimate beginner's guide to Brad Pitt

Brad Pitt has established himself as one of the biggest names in Hollywood, known for his stellar performances in some of the most iconic projects of the last few decades like Fight Club, Inglourious Basterds, Once Upon a Time In Hollywood and countless others. Although he was typecast for his looks, Pitt has worked hard to steer away from being stereotyped by proving that he has the acting talent to match the very best.

When he was younger, Pitt was wanted to become an art director but he fell in love with cinema and called it “a portal into different worlds”. Desperate to make it as an actor, he moved to Los Angeles and worked in a number of odd jobs including a brief stint as a limousine driver tasked with the responsibility of driving strippers around.

Drawing inspiration from the likes of Sean Penn, Gary Oldman and Mickey Rourke, Pitt eventually entered the film industry and worked his way to the very top. It all paid off in the end because Pitt is one of the most celebrated actors in the world, recognised all over the world for his invaluable contributions to the world of cinema.

Check out a list of Brad Pitt’s definitive films below.

Brad Pitt’s six definitive films:

Thelma & Louise (Ridley Scott, 1991)

Ridley Scott’s 1991 road film was the one that kickstarted Pitt’s career, starring him as an attractive drifter with a cowboy spirit. Thelma & Louise revolves around the misadventures of the titular women but Pitt managed to leave a lasting impression through his memorable appearance.

Referring to the film as “the big league”, Pitt has always maintained that it was because of Scott’s willingness to take a chance on him that he managed to succeed as an actor. Pitt said: “I had nothing to show for myself, except for my work as an extra, and they took a chance on me”.

12 Monkeys (Terry Gilliam, 1995)

Another enigmatic cult classic from the earlier half of Pitt’s acting career, Terry Gilliam’s 1995 sci-fi masterpiece is actually an extension of a French New Wave classic called La Jetée by Chris Marker. 12 Monkeys envisions a future where an engineered, lethal virus has ravaged modern society.

In order to save humanity, a convict is sent back in time to help come up with information for a possible cure to this pressing problem. Pitt is fantastic as Jeffrey Goines, a mental patient who has some pretty lucid ideas about corporatism and environmental concerns.

Fight Club (David Fincher, 1999)

Undoubtedly the most popular and widely quoted role that Pitt has ever played, Fight Club is one of those enduring cultural artefacts of the ’90s that is still cited as a brilliant cinematic investigation of consumerism, hyper-capitalism and the problems of masculinity in the modern age.

Pitt is endlessly alluring as Tyler Durden, a mysterious soap salesman who appears to be a covert revolutionary spearheading an important movement which articulates the pain of existing in a world like ours. Sadly, many young viewers fail to recognise that he is also a part of the problem and not the solution.

The Assassination of Jesse James by the Coward Robert Ford (Andrew Dominik, 2007)

A neglected masterpiece from Pitt’s filmography, Andrew Dominik’s 2007 revisionist western stars Pitt as the iconic American outlaw Jesse James and explores his relationship with the man who finally killed him – Robert Ford (played by Casey Affleck).

Roger Deakins’ fantastic cinematography earned an Academy Award bid for its unique vision, one of the last features Deakins ever shot on film before making the switch to digital. Pitt is fantastic as James, delivering an unpredictable performance that is underlined by pathos and violence.

The Tree of Life (Terrence Malick, 2011)

An essential part of Malick’s body of work as well as Pitt’s, The Tree of Life is a sprawling opus which tries to investigate the origins of life through the story of a Midwestern family. The film uses the troubled relationship between a father (Brad Pitt) and his son (Sean Penn) to ask greater questions about the human condition.

“Experience it like a walk in the countryside,” Malick suggested, while talking about the unique cinematic experience that The Tree of Life offers. “You’ll probably be bored or have other things in mind, but perhaps you will be struck, suddenly, by a feeling, by an act, by a unique portrait of nature.”

Once Upon a Time in Hollywood (Quentin Tarantino, 2019)

One of the most high-profile projects that Pitt has undertaken, Once Upon a Time in Hollywood pairs him up with Leonardo DiCaprio while conducting a revision of the Manson murders. Pitt is brilliant as Cliff Booth, a loyal assistant to a fading actor (DiCaprio) who finds himself in absurd circumstances.

The highly lauded directorial effort from Tarantino gave Pitt the chance to produce some of his best work in recent memory, conducting a sincere portrayal of a man struggling to make it in Hollywood. Pitt went as far as to declare: “Quentin Tarantino is the last purveyor of cool.”