Pitt had some early success in the late 1980s after starring in a number of independent films, but it was his appearance in Ridley Scott’s Thelma & Louise that truly introduced him to Hollywood. Although co-stars Geena Davis and Susan Sarandon were already household names, it was Pitt who stole the spotlight for his appearance as J.D.

Davis, who had a love scene with Pitt in the movie, wrote in her memoir Dying of Politeness that the actor had been concerned about a small pimple on his butt, which was subsequently covered up by the make-up assistant.

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2. Sleepers (1996)

Director Barry Levinson took charge of this dramatic thriller released in 1996. Starring Jason Patric, Billy Crudup and Ron Eldard, the film explores the friendship between childhood friends and how a prank lands the boys in a detention centre, which alters the course of their life.

Pitt plays the most central role in the film: Michael Sullivan, who devises a plan after his friends sought vengeance for the trauma they endured at the detention centre. Pitt portrayed the character with effortless ease.

3. The Counsellor (2013)

Another Scott crime thriller that didn’t make an impression was this 2013 flick. The film centres around a lawyer played by Michael Fassbender known as the titular counsellor who attempts to buy a ring for his fiancée, played by Penélope Cruz. He reaches out to an exotic dealer played by Javier Bardem. Despite the A-list cast, the film was widely considered a flop, but Pitt’s performance has been singled out.

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4. Killing Them Softly (2012)

This crime comedy with sprinkles of political commentary sees Pitt starring as Jackie Cogan, who is hired to restore order in the criminal economy after three men rob a mob-protected card game. James Gandolfini and Ben Mendelsohn are brilliant at cultivating an atmosphere for deadpan humour. Pitt and dark comedy go well together, as seen in his previous roles of Snatch and Inglourious Basterds, and at the time this was considered one of his most underrated roles.

5. Voyage of Time (2016)

This documentary by Terrence Malick details the creation of the universe and the origin of life on earth. Not only did Pitt produce the documentary, he also served as its narrator. His drawn-out voice is the perfect match for the rich visuals Malick used. Although not a starring role, Pitt’s dual role as producer and narration showcases the actor’s diverse skill set.

6. By the Sea (2015)

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7. Cutting Class (1989)

In one of his earliest film roles, Pitt stars in this 1989 slasher flick directed by Rospo Pallenberg. The plot revolves around a number of student disappearances at school, and this classic “whodunnit” flick has all the suspense needed to keep viewers on the edge of their seats. Pitt plays Dwight Ingalls, the boyfriend to the heroine of the film. The film didn’t make much of an impact, but it gave viewers a taster as to what Pitt would be capable of.

8. Friends (2001)

Having a cameo on popular sitcom Friends was common in Hollywood in the noughties. From Sean Penn to Bruce Willis and Julia Roberts, the series wasn’t short on big names who were more than willing to star in the hit show. In 2001, Pitt appeared as a guest star. He was married to Jennifer Aniston (who plays Rachel on Friends) at the time, and the episode quickly became a historic silver screen moment: Pitt played the role of Will, a former classmate who used to hate Rachel.