Brad Pitt’s acting career has spanned over four decades, and is still going strong. He’s played numerous prominent and iconic roles that have made him one of the most popular leading men in Hollywood—but how do they stack up with the critics? This list only takes into account films starring Pitt. Though critical hits12 Years A SlaveandThelma and Louisehave scenes with Pitt, he’s only a featured player.

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Two detectives escorting a prisoner

Therefore, those movies are booted off in favor of two others where Pitt plays a main character. There are some very popular movies that didn’t make the cut, likeFight Club,and also a couple that might be surprising, like one of his newer movies,Ad Astra.

10.Se7en(1995) - Tomatometer: 82%, Audience Score: 95%

Detective Somerset (Morgan Freeman) is about to retire, but not before he takes on one last case with the young, newly transferred detective David Mills (Brad Pitt). They soon discover a pattern of a serial killer who is taking out people to represent the Seven Deadly Sins.

Freeman and Pitt are a perfect combo in this crime thriller. It is a dark, ominous, creepy movie with a fascinating plot and compelling characters. And of course, Pitt delivers his famous, “What’s in the box!?“line at the end of this film.

George Clooney, Brad Pitt, Matt Damon, Elliot Gould, Don Cheadle (left to right)

9.Ocean’s Eleven(2001) - Tomatometer: 83%, Audience Score: 80%

An absolutely star-studded cast headlines one of the best heist movies ever, aremake of the Rat-Pack’sOcean’s 11.Pitt plays the right-hand man of Danny Ocean (George Clooney), Rusty Ryan. Danny, Rusty, Linus (Matt Damon) and the rest of their crew plan an elaborate heist to simultaneously rob the Bellagio, Mirage and MGM Grand casinos.

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It’s charming, witty, funny, and keeps you on your toes throughout with a few twists. Pitt and Clooney’sOcean’scast spawned two sequels,Ocean’s TwelveandOcean’s Thirteen.Although they aren’t as highly acclaimed as the first one, they’re still pretty solid and just as fun.

A shockingly low Audience Score for this movie, and by far the biggest difference between Tomatometer and Audience Score on the list. Ad Astra follows fearless astronaut Roy McBride, who is summoned to travel into deep space to solve the mystery of his father, Clifford McBride (Tommy Lee Jones) and his crew.

Brad Pitt (middle) in Tree of Life

The movie is visually stunning, the soundtrack is great, and it is an overall fantastic deep space sci-fi flick. It follows a world where interplanetary travel is a norm, and deep space exploration is not all that difficult. It’s an emotional journey,and a story between a son and father.

7.The Tree of Life(2011), Tomatometer: 84%, Audience Score: 60%

Pitt plays Mr. O’Brien alongsideJessica Chastain(Mrs. O’Brien), asSean Pennplays an older version of their son, Jack. The film is deeply philosophical, with questions and themes about life, faith, loss, adolescence, and much more.

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The film explores nurture vs nature, as Mrs. O’Brien presents herself and the world as a place of love, while Mr. O’Brien has difficulties fully expressing his love to his sons, and is quick to his temper, though it is because he believes the world is harsh and unforgiving.

6.Once Upon a Time…in Hollywood(2019), Tomatometer: 85%, Audience Score: 70%

Quentin Tarantino’smost recent movie, much likeInglorious Basterds(2009), is a period piece. Taking place in 1960s Los Angeles, Pitt plays Cliff Booth, the longtime stuntman to Rick Dalton (Leonardo DiCaprio) as they both struggle to fit into the changing landscape of Hollywood.

Booth is not only a stuntman, but many people believe he got away with killing his wife, leaving a mysterious angst surrounding his character. And of course, Dalton lives next-door to Sharon Tate.

Brad Pitt in Once Upon a Time in Hollywood

5.12 Monkeys(1995), Tomatometer: 88%, Audience Score: 88%

James Cole (Bruce Willis) gets sent back in time to stop a deadly virus from being released in 1996, wiping out most humanity and leaving the survivors to live underground. Cole, while in a mental hospital, meets Jeffrey Goines (Brad Pitt).

This movie is a trip, and Brad Pitt is even a bigger trip in it. Many consider the manic Jeffrey Goines to be one of Pitt’s best roles to date; it was a phenomenal individual performance. His mannerisms and facial expressions are off the chart; it’s impossible to take your eyes off him when he’s on-screen.

Bruce Willis (left) and Brad Pitt (right) in 12 Monkeys

4.The Big Short(2015), Tomatometer: 89%, Audience Score: 88%

The Big Shortis anAdam McKaysatirical-comedy-drama that revolves around the 2008 housing market crash and subsequent economic collapse. One of the unique parts of this movie is howit gets celebrities to cameo and explain termsto the greater audience who may not be familiar.

Pitt plays Ben Rickert, based onBen Hockett,who is a retired trader. Ben helps young investors Charlie (John Magaro) and Jamie (Finn Wittrock) sell their swaps and make them tens of millions of dollars.

3.Inglorious Basterds(2009), Tomatometer: 89%. Audience Score: 88%

Pitt plays Lt. Aldo Raine, who boasts a mustache and a nasty scar across his neck. Raine assembles a group of eight Jewish soldiers to hunt Nazi soldiers with extreme violence. The unit scalps Nazis after killing them for trophies, and occasionally will leave one alive to tell the tale of their group, but not before carving a Swastika into their skin.

Pitt delivers yet another iconic performance with Aldo Raine, who is serious and often funny (though most of the time it isn’t on purpose). The only thing that trumps Pitt’s accent as Raine is when Raine attempts an Italian accent.Arrivederci.

2.True Romance(1993), Tomatometer: 93%, Audience Score: 93%

This is technically cheating, because Pitt plays a supporting role here. However, it would be criminal not to include one of Pitt’s most memorable performances from an excellent movie.

Directed byTony Scott, you can feel Tarantino’s fingerprints all over this movie, since he wrote the screenplay. Pitt plays Floyd, who is Dick Ritchie (Michael Rapaport)’s stoner roommate. His screen time is limited, but every scene he is in is hilarious, some of the best parts of the movie. “They were here, then they said they were going to go there. Then they went.”

1.Moneyball(2011), Tomatometer: 94%, Audience Score: 86%

Pitt playsBilly Beane,General Manager for the Oakland A’s, who tries to make due with a small budget by hunting for players other scouts deemed “flawed.” Beane’s philosophy is backed by Ivy Leaguer Peter Brand, who uses analytics more than anything else: hit home runs, get on base. That’s the motto.

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It is worth noting that while this is a philosophy that did well and is heavily used in baseball today,Moneyballfails to highlight that the 2002 A’s had MVP ShortstopMiguel Tejada, and one of the best pitching rotations in baseball withBarry Zito,Mark MulderandTim Hudson. Still a captivating and fantastic movie though.

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