Brad Pitt has been around as a top star in Hollywood for a long time now, even longer than his most recent character Jack Conrad in Babylon. In that time, he has accumulated a variety of incredible on-screen performances that have enchanted audiences across genres.

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Notable earlier in his career as a heartthrob, Pitt has gone through a number of reinventions to keep himself fresh and at the top of Hollywood. From Oscar-winning masterpieces to war movies, comedic absurdities, and even co-starring with a dinosaur, nothing has stopped Brad Pitt or halted his success across five decades as a star.

9 Once Upon A Time In Hollywood

Brad Pitt In Once Upon A Time In Hollywood

His second teaming with Quentin Tarantino and a fascinating film that handled DiCaprio and Pitt as an actor and a stuntman living in Hollywood in 1969, Once Upon A Time In Hollywood was one of those special, strange films that showcased the acting abilities of Pitt in a way few of the films he stars in manage.

It was a beautiful meditation on the last of Hollywood’s golden years, and the playfully strange relationship it has with history made for a fascinatingly unpredictable story with this incredible duo of actors at the heart of it.

8 Allied

Brad Pitt In Allied

Allied came out in 2016 and starred Brad Pitt as an intelligence agent working during World War II for the allied forces. He meets and falls in love with a French resistance fighter, played by Marion Cotillard, and they get married while the war rages on.

Trouble starts in their marriage though when Pitt’s character is informed that his wife is a German spy, and he begins to suspect that this may be true. A story of war and romance, this espionage-based flick was one of Pitt’s few failures at the box office but is underrated and features a particularly great performance from Pitt himself.

7 The Big Short

Brad Pitt In The Big Short

Pitt has never been shy about sharing the spotlight in his major flicks, he has always enjoyed ensemble movies. This includes Adam McKay’s true-to-life tale about a variety of characters that were involved in the 2008 housing market crash in the United States.

Pitt plays Ben Rickert alongside the likes of Steve Carell, Ryan Gosling, and Christian Bale. The huge cast helped this film become a huge hit despite the dense, financially-based subject material, and Pitt’s performance was lauded as part of this incredible ensemble brought together.

6 Fury

Brad Pitt In Fury

Another ensemble film, though one where Pitt’s character stood out as the particular lead, Fury was a war film set in the final weeks of World War II as American tanks helped push Nazi forces back through the heart of Germany in brutal battles.

The five-man tank crew led by Pitt’s character Wardaddy were all played to perfection, and the horrors of war are mixed with emotional moments and great action scenes, making for a brilliant modern war film that didn’t get enough recognition when it was released in 2014.

5 Moneyball

Brad Pitt In Moneyball

A huge shift for Pitt at the time when it was released in 2011, Moneyball was Pitt’s first dealing with a financial film, and a sports one as well. Moneyball is about a baseball manager, played by Pitt, who works with an economics graduate to try and make a professional baseball team using computer-based methods.

Related:Best Sci-Fi Movies Set On The MoonThe film was a standout in the awards season for that year, and with other big cast members such as Chris Pratt and Robin Wright along for the ride, Pitt once again capably looked like the leading man of this big cast that put together and told a wonderful, intricate story about the complex subject.

4 Spy Game

Brad Pitt In Spy Game

Spy Game is an earlier performance of Pitt’s and one where he played the younger fiddle to a legendary actor in the guise of Robert Redford. The two played a spy duo in a tense thriller that dealt with some of the more desk-based realities of covert intelligence operations.

The film follows Redford’s character on his last day before retirement at the CIA, as he tries to get a death sentence placed upon Pitt’s character nixed before he leaves. Their story told in flashbacks over many years, is intricate, well-written, and brilliantly acted by both men.

3 Inglourious Basterds

Brad Pitt In Inglourious Basterds

His first teaming with Quentin Tarantino, Inglorious Basterds is yet another time that Brad Pitt went to World War II. This time, he was leading a ridiculous Jewish-American troupe that was attempting to bring down the Nazi government during the war.

The story, the ensemble cast, and Pitt’s character, in particular, helped to make this simultaneously Tarantino’s most insane and yet most hilariously wonderful film ever. Pitt’s performance was pitch-perfect and a stand-out alongside that of Christoph Waltz, and it has now become one of the absolute best films of Pitt’s storied career.

2 Se7en

Brad Pitt In Se7en

Pitt has made so many legendary films in the last twenty years, it would be easy to forget he’d already solidified his place in history with incredible performances in the 90s. Se7en was one of his few ventures into slower-paced investigative films, and the bloody, brutal film has gone down in history for his and his partner Morgan Freeman’s performances.

Se7en is about a serial killer attempting to murder prominent people around New York using methods that showcase each of the seven deadly sins. One scene, in particular, involving a box is memorable for Pitt’s incredible acting.

1 Fight Club

Brad Pitt In Fight Club

But Pitt’s very best performance came a couple of years after Se7en in Fight Club. One of the most memorable and legendary films of all time, Fight Club stars Edward Norton and Brad Pitt as quite literally two sides of the same coin.

The film deals with an uprising of men who decide that their boring, everyday lives aren’t what they really want, as they all slowly become addicted to the violence of punching each other in the face in a basement instead. Sounds ridiculous, but Pitt’s performance as the charismatic Tyler Durden helped turn this into a legend.

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