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Best Brad Pitt movies

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Heyday Films

Best Brad Pitt movies

Between “Once Upon a Time in Hollywood” and the current release of “Ad Astra,” it's been a Brad Pitt summer and fall. What’s most surprising is that Pitt is still acting at all. In 2011, he told Australia’s “60 Minutes” that he planned to give up on starring in movies by the age of 50. He’s now 55 and gracing at least two separate screens at the nearest cineplex, delivering two praiseworthy performances in the process. And it’s definitely not because he needs the money.

The path to global stardom wasn’t exactly clear cut for Pitt, who grew up in Shawnee, Okla. An athletic student with a broad spectrum of interests and hobbies, he enrolled in the University of Missouri and majored in journalism. It was upon graduating that he realized his passion for film was too powerful to ignore. That brought him to Los Angeles, where he attended acting workshops, took odd jobs, landed uncredited roles in various movies, and appeared on TV shows like “Dallas” and “21 Jump Street.” 

Famously, Pitt’s big break came when he snagged the role of a grifter named J.D. in 1991’s “Thelma & Louise.” As subsequent offers came pouring in, the actor ascended to A-list status in just a few years’ time. Reluctant to play the straight-laced man or romantic lead, he opted instead for a variety of interesting and challenging roles. He generated a diverse repertoire, which comes filled to the brim with eccentric characters and heroic ones alike. Equally diverse is his evolving reputation, which swings from pot-loving heartbreaker to global humanitarian.  

As his career progressed, Pitt shifted toward production while continuing to star in several films. In 2001, he co-founded Plan B Entertainment, taking sole ownership four years later. Wildly successful in its own right, Plan B has produced everything from crowd-pleasers like “Eat, Pray, Love” to blockbusters such as “World War Z” to Oscar-winners like “12 Years a Slave” and “Moonlight.” Add to that Pitt’s various charitable causes and high-profile relationships and it’s safe to say the man keeps busy on both sides of the camera. 

Despite his many achievements in a variety of fields, Brad Pitt remains best-known as an accomplished actor. Today, Stacker is ranking his movies from worst to best. For the list, Stacker compiled all the IMDb data on feature films and TV movies featuring Brad Pitt as an actor. Each film was ranked according to its user rating and any ties were broken by the number of votes. Cameos, uncredited roles, and production credits without acting roles were not considered. Here are Pitt’s best (and worst) movies. 

You may also like: Best Robert De Niro movies

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April Films

#49. Cutting Class (1989)

Directed by Rospo Pallenberg

- IMDb user rating: 4.4
- Votes: 3,978
- Metascore: N/A
- Runtime: 91 min

Pitt made his big-screen debut in this campy slasher flick, which centers on a high school girl and her two suitors. One suitor is a homicidal maniac and the other one is Brad Pitt. Decisions, decisions. 

 

3/
Bakshi Animation

#48. Cool World (1992)

Directed by Ralph Bakshi

- IMDb user rating: 4.9
- Votes: 19,407
- Metascore: 28
- Runtime: 102 min

From “Fritz the Cat” creator Ralph Bakshi comes this noirish blend of animation and live-action, which ultimately feels like a low-rent follow-up to “Who Framed Roger Rabbit?” Pitt plays the role of Frank Harris, the only human in an otherwise cartoon world. Despite tanking at the box office, this was among the first film’s to actualize Pitt’s potential as a leading Hollywood man. 

4/
Nelson Entertainment

#47. The Favor (1994)

Directed by Donald Petrie

- IMDb user rating: 5.2
- Votes: 2,405
- Metascore: 51
- Runtime: 97 min

Filmed in 1990 and then released four years later, this romantic comedy stars Pitt in a supporting role. At the heart of the story is a married woman named Kathy (Harley Jane Kozak), who wonders what it would be like to sleep with another man (Ken Wahl). When she asks her friend Emily (Elizabeth McGovern) to do the deed on her behalf, it kicks off a string of disastrous events.  

5/
Universal Pictures

#46. By the Sea (2015)

Directed by Angelina Jolie

- IMDb user rating: 5.3
- Votes: 16,534
- Metascore: 44
- Runtime: 122 min

The only film to star both Brad Pitt and Angelina Jolie when they were married is also one of the worst efforts of their respective careers. Jolie wrote and directed the movie (as Angelina Jolie Pitt), hoping it would help improve their waning relationship. Fittingly, it tells the story of a couple trying to save their marriage while staying in France.  

6/
Fox 2000 Pictures

#45. The Counsellor (2013)

Directed by Ridley Scott

- IMDb user rating: 5.3
- Votes: 92,716
- Metascore: 48
- Runtime: 117 min

Expectations were high for this disappointing crime drama, which put a slate of A-list talent both in front of and behind the camera. Starring alongside Cameron Diaz, Michael Fassbender, Penélope Cruz, and Javier Bardem, Pitt plays a shady middle man named Westray. A critical and commercial flop, the movie features one heck of a death sequence toward the end. 

 

7/
Avala Film

#44. The Dark Side of the Sun (1988)

Directed by Bozidar 'Bota' Nikolic

- IMDb user rating: 5.5
- Votes: 3,167
- Metascore: null
- Runtime: 101 min

Brad Pitt was a complete unknown when he scored his first starring role in this Yugoslavian drama, playing a man with a rare skin disease. Tensions were high during the on-location shoot, as former Yugoslavia teetered closer to a decade-long civil war. The movie was shelved upon completion and then released straight to video in 1997.

 

8/
Tung Films

#43. Across the Tracks (1990)

Directed by Sandy Tung

- IMDb user rating: 5.8
- Votes: 1,968
- Metascore: null
- Runtime: 100 min

Pitt stars opposite former child actor Ricky Schroder in this high school sports drama about two teenage brothers named Joe and Billy. As Joe (Pitt) competes on the track team and pursues a college scholarship, Billy (Schroder) grapples with a life of crime and substance abuse. When it turns out that Billy is a talented runner in his own right, an athletic rivalry develops. 

9/
Arena

#42. Johnny Suede (1991)

Directed by Tom DiCillo

- IMDb user rating: 5.8
- Votes: 3,485
- Metascore: 53
- Runtime: 97 min

Arriving just months after “Thelma & Louise,” this indie comedy centers on an aspiring musician named Johnny Suede. Director Tom DiCillo insisted on casting a then-unknown Brad Pitt in the lead role, later describing the actor’s performance as some of his “best work.” Miramax purchased the film in 1990 and released it the following year, hoping to “capitalize on Pitt’s ascending stardom.”

10/
Frank & Bob Films II

#41. Too Young to Die? (1990)

Directed by Robert Markowitz

- IMDb user rating: 5.9
- Votes: 3,502
- Metascore: null
- Runtime: 92 min

Before teaming up for 1993’s “Kalifornia,” Pitt and actress Juliette Lewis co-starred in this TV movie. Loosely based on a true story, it chronicles the murder trial of an abused 15-year-old named Amanda Sue Bradley (Lewis). After shooting wrapped, Pitt and Lewis began dating

 

11/
Warner Bros.

#40. Happy Feet Two (2011)

Directed by George Miller, Gary Eck, David Peers

- IMDb user rating: 5.9
- Votes: 38,921
- Metascore: 50
- Runtime: 100 min

Pitt lent his voice to the role of Will the Krill for this computer-animated sequel, which drastically underperformed at the box office. Determined to scrap his way out from the bottom of the food chain, Will attempts to become an apex predator. The move sparks hostility between Will and his best friend Bill, voiced by Matt Damon. 

 

12/
Apollo Productions

#39. Happy Together (1989)

Directed by Mel Damski

- IMDb user rating: 6.0
- Votes: 1,500
- Metascore: null
- Runtime: 102 min

Because of a computer glitch, an ambitious male freshman (Patrick Dempsey) ends up with a party-loving female (Helen Slater) for a roommate. So goes this indie comedy from 1989, which stars Pitt in the bit role of Brian. It opened in 10 theaters nationwide and made just under $71,000 at the domestic box office. 

[Pictured: Helen Slater and Patrick Dempsey in Happy Together, 1989]

13/
Hurwitz Creative

#38. War Machine (2017)

Directed by David Michôd

- IMDb user rating: 6.0
- Votes: 35,850
- Metascore: 56
- Runtime: 122 min

On the heels of movies like “Beasts of No Nation,” Netflix continued to strive for reputable fare with this somewhat middling satire. Brad Pitt stars as General Glen McMahon, who is sent to “clean up” the mess in Afghanistan. Spoiler alert: He doesn’t succeed. 

 

14/
DreamWorks

#37. The Mexican (2001)

Directed by Gore Verbinski

- IMDb user rating: 6.1
- Votes: 98,098
- Metascore: 43
- Runtime: 123 min

Pitt was at the height of his star power when he headlined this adventure comedy alongside fellow A-lister Julia Roberts. Despite its potential as a rollicking road movie, the film’s poor plotting and drawn-out pacing turned off a number of fans and critics. Pitt and Roberts also co-starred in “Ocean’s Eleven,” released later that same year.  

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Columbia Pictures

#36. The Devil's Own (1997)

Directed by Alan J. Pakula

- IMDb user rating: 6.2
- Votes: 54,388
- Metascore: 53
- Runtime: 111 min

Back when adult crime dramas were a bankable genre, Brad Pitt starred in this one as an IRA terrorist named Frankie McGuire. Upon being sent to the U.S. to buy weapons, McGuire adopts an alias and stays under the roof of NYPD sergeant Tom O'Meara (Harrison Ford). It paves the way for an unlikely friendship, which gets put to the test when Frankie’s true identity is revealed. 

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Plan B Entertainment

#35. Killing Them Softly (2012)

Directed by Andrew Dominik

- IMDb user rating: 6.2
- Votes: 125,044
- Metascore: 64
- Runtime: 97 min

Adult crime dramas were definitely not a bankable genre by 2012, as this retro-flavored box office turkey goes to show. It stars Pitt as the mob enforcer Jackie Cogan, who’s hired to track down and kill three amateur stick-up artists. This marked the third time Pitt shared a billing with actor James Gandolfini, former co-star in both 1993’s “True Romance” and 2001’s “The Mexican.”

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Warner Bros.

#34. Ocean's Twelve (2004)

Directed by Steven Soderbergh

- IMDb user rating: 6.5
- Votes: 335,166
- Metascore: 58
- Runtime: 125 min

Danny Ocean (George Clooney) and his gang of charming thieves reunite in this lucrative sequel. Like both its predecessor and successor, the movie stars a veritable bounty of A-list talent. Pitt reprises the role of Rusty Ryan, Ocean’s coy right-hand man who oversees day-to-day operations. 

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Regency Enterprises

#33. Mr. & Mrs. Smith (2005)

Directed by Doug Liman

- IMDb user rating: 6.5
- Votes: 422,318
- Metascore: 55
- Runtime: 120 min

It might have sparked one of the most dramatic love affairs in tabloid history, but this smash hit keeps a light tone from start to finish. Beneath the veneer of their mundane marriage, a husband (Pitt) and wife (Angelina Jolie) lead double lives as secret assassins. When they’re assigned to kill one another, it provides the perfect jolt to their ailing relationship.

19/
DreamWorks

#32. Sinbad: Legend of the Seven Seas (2003)

Directed by Patrick Gilmore, Tim Johnson

- IMDb user rating: 6.7
- Votes: 45,400
- Metascore: 48
- Runtime: 86 min

Most animated fare is a recipe for box office success, but not this forgotten bomb from 2003. Pitt provides the voice of mythic sailor Sinbad, who travels to the end of the world in search of a stolen book. Critics were more or less uniformly impressed with the animation, but otherwise divided on the script. 

20/
PolyGram Filmed Entertainment

#31. Kalifornia (1993)

Directed by Dominic Sena

- IMDb user rating: 6.7
- Votes: 48,127
- Metascore: 49
- Runtime: 117 min

Pitt was ascending the Hollywood ranks when he took a minor detour, starring in this quirky crime drama. It follows a journalist (David Duchovny) and his girlfriend on a road trip across America, as part of a research project involving famous serial killers. Joining them for the ride are Early Grayce (Pitt) and Adele Corners (Juliette Lewis), who have firsthand knowledge of the subject.  

21/
Cottonwood Pictures

#30. The Tree of Life (2011)

Directed by Terrence Malick

- IMDb user rating: 6.8
- Votes: 157,765
- Metascore: 85
- Runtime: 139 min

Brought to life through Terrence Malick’s stunning visual palette, this Oscar-nominated drama tells the story of a Texan family in 1956. Jumping as far ahead as the present day and as far back as the beginning of the universe, the film grapples with both metaphysical and interpersonal themes. Brad Pitt portrays the family patriarch and Jessica Chastain plays his wife. 

22/
Warner Bros.

#29. Ocean's Thirteen (2007)

Directed by Steven Soderbergh

- IMDb user rating: 6.9
- Votes: 300,618
- Metascore: 62
- Runtime: 122 min

Marking a conscious return to form, the third installment of the “Ocean’s Eleven” franchise pits Danny Ocean (Clooney) and his crew against casino owner Willy Bank (Al Pacino). As always, it was a convivial affair both on and off-screen for all those involved. In an interview, Pitt and Clooney confirmed that director Steven Soderbergh jokingly referred to this film as “Ocean’s Thirteen: The One We Should Have Made Last Time.”

23/
Focus Features

#28. Burn After Reading (2008)

Directed by Ethan Coen, Joel Coen

- IMDb user rating: 7.0
- Votes: 290,905
- Metascore: 63
- Runtime: 96 min

On the heels of “No Country for Old Men,” the Coen brothers released this farcical black comedy to strong box office numbers. After chancing upon a former CIA agent’s (John Malkovich) missing documents, two gym employees (Pitt and Frances McDormand) enact a hair-brained blackmail scheme. It re-teamed Pitt with former “Ocean’s Eleven” franchise co-star George Clooney.

 

24/
Paramount Pictures

#27. World War Z (2013)

Directed by Marc Forster

- IMDb user rating: 7.0
- Votes: 560,513
- Metascore: 63
- Runtime: 116 min

Adapted from the best-selling novel, this action horror movie follows a man (Pitt) and his family through the zombie apocalypse. In the wake of a famously troubled production, the film earned Pitt his highest returns at the domestic box office (not counting cameos). He and director David Fincher were attached to a long-awaited sequel, which was shut down due to reported budget issues

25/
Mandalay Entertainment

#26. Seven Years in Tibet (1997)

Directed by Jean-Jacques Annaud

- IMDb user rating: 7.1
- Votes: 114,602
- Metascore: 55
- Runtime: 136 min

This 1997 drama tells the true story of Austrian climber Heinrich Harrer (played here by Pitt), who visits Tibet and befriends the Dalai Lama amidst a backdrop of political unrest. Because of his role in the film, Pitt was banned from entering China for a number of years. On Empire’s list of the Top Ten Worst Movie accents, his Austrian accent landed at number three. 

26/
Paramount Pictures

#25. Allied (2016)

Directed by Robert Zemeckis

- IMDb user rating: 7.1
- Votes: 128,494
- Metascore: 60
- Runtime: 124 min

rumored affair between Pitt and co-star Marion Cotillard wasn’t enough to drum up interest in this British-American war thriller, which tanked at the domestic box office. Set at the height of WWII, it centers on the romance between a Canadian intelligence officer (Pitt) and French resistance fighter (Cotillard). Critic Peter Sobczynski gave the film a four-star review on Roger Ebert, citing it as an “entertaining stab at old-fashioned storytelling.”

27/
Universal Pictures

#24. Spy Game (2001)

Directed by Tony Scott

- IMDb user rating: 7.1
- Votes: 137,006
- Metascore: 63
- Runtime: 126 min

Filmed in Tony Scott’s signature kinetic style, this 2001 thriller stars Brad Pitt as superspy Tom Bishop. After being arrested in China on espionage charges, Bishop’s former mentor (Robert Redford) concocts a plan to spring him free. Interspersed throughout are flashback sequences, chronicling the turbulent relationship between the two men. 

28/
Allied Filmmakers

#23. A River Runs Through It (1992)

Directed by Robert Redford

- IMDb user rating: 7.2
- Votes: 49,608
- Metascore: 68
- Runtime: 123 min

Years before they teamed up in “Spy Game,” Robert Redford directed Pitt in one of his earliest breakout performances. Based on a semi-autobiographical novel, the film takes place in rural Montana from the WWI-era through to the Great Depression. As two brothers drift apart, one (Craig Sheffer) embarks down a straight and narrow path while the other (Pitt) succumbs to self-destruction. 

29/
Universal Pictures

#22. Meet Joe Black (1998)

Directed by Martin Brest

- IMDb user rating: 7.2
- Votes: 197,634
- Metascore: 43
- Runtime: 178 min

His name is Joe Black, but he’s also known as Death in this 1998 fantasy drama, which stars Pitt in the title role. While learning about life on Earth with help from a media mogul (Anthony Hopkins), Black falls in love with the mogul’s daughter (Claire Forlani). The movie was more or less forgotten until its most ridiculous scene went viral in 2019. 

30/
DreamWorks Animation

#21. Megamind (2010)

Directed by Tom McGrath

- IMDb user rating: 7.2
- Votes: 211,190
- Metascore: 63
- Runtime: 95 min

“He looks a bit like Clooney,” Pitt once said of his superhero counterpart in this computer-animated adventure comedy. That superhero goes by the name of Metro Man, and he’s constantly squaring off against a villain named Megamind (voiced by Will Ferrell). When Megamind gets the upper hand for good, it leads to an existential crisis. 

31/
Warner Bros.

#20. Troy (2004)

Directed by Wolfgang Petersen

- IMDb user rating: 7.2
- Votes: 457,759
- Metascore: 56
- Runtime: 163 min

Before adapting “Game of Thrones” for HBO, writer David Benioff penned the script to this historical epic. Taking cues from Homer’s “Iliad,” it depicts an abridged version of the Trojan War. Pitt stars as Achilles, the fearless warrior whose fatal weakness remains the stuff of legend.

32/
Pathé Entertainment

#19. Thelma & Louise (1991)

Directed by Ridley Scott

- IMDb user rating: 7.4
- Votes: 124,000
- Metascore: 88
- Runtime: 130 min

Brad Pitt delivered his breakout performance in this iconic road movie, playing a smooth-talking grifter named J.D. It was an extremely lucky break for Pitt, who only landed the part after two other actors dropped out. The film follows two women (Geena Davis and Susan Sarandon) on an impromptu crime spree of still-famous proportion. 

 

33/
Paramount Pictures

#18. Babel (2006)

Directed by Alejandro G. Iñárritu

- IMDb user rating: 7.4
- Votes: 275,473
- Metascore: 69
- Runtime: 143 min

Using loosely interconnected narratives, director Alejandro G. Iñárritu explores themes of humanity and fate in this multi-dimensional drama. Pitt and Cate Blanchett star as the married couple Richard and Susan, who experience unexpected tragedy while vacationing in Morocco. Because the movie was shot in various locations around the world, Pitt and Blanchett didn’t meet several co-stars until the premiere

34/
TriStar Pictures

#17. Legends of the Fall (1994)

Directed by Edward Zwick

- IMDb user rating: 7.5
- Votes: 135,200
- Metascore: 45
- Runtime: 133 min

Pitt secured his A-list status by headlining this sweeping drama, which takes place in early 20th-century Montana. When two brothers (Pitt and Aidan Quinn) fall in love with the same woman (Julia Ormond), it threatens to tear an entire family apart. Reflecting upon the film in 2014, Ormond described Pitt as a dedicated character actor who was reluctant to become the next Hollywood heartthrob. 

35/
Warner Bros.

#16. The Assassination of Jesse James by the Coward Robert Ford (2007)

Directed by Andrew Dominik

- IMDb user rating: 7.5
- Votes: 158,472
- Metascore: 68
- Runtime: 160 min

Co-produced by and starring Pitt, this 2007 Western chronicles the final months of infamous outlaw Jesse James (Pitt). It failed to penetrate the box office during a theatrical run, but has since garnered a healthy cult following. In a 2017 interview with GQ, Pitt referred to this film as his personal favorite.

36/
Astoria Films

#15. Sleepers (1996)

Directed by Barry Levinson

- IMDb user rating: 7.6
- Votes: 176,822
- Metascore: 49
- Runtime: 147 min

After a prank goes awry, four boys from Hell’s Kitchen are sent to a brutal detention facility. Reuniting 13 years later, they seek revenge on their former abusers. Pitt stars alongside a talented cast, which includes Kevin Bacon, Robert De Niro, Dustin Hoffman, and Minnie Driver. 

37/
Geffen Pictures

#14. Interview With the Vampire: The Vampire Chronicles (1994)

Directed by Neil Jordan

- IMDb user rating: 7.6
- Votes: 277,028
- Metascore: 59
- Runtime: 123 min

Anne Rice’s best-selling novel leapt onto the big screen in 1994, with Pitt tackling the role of Louis Pointe du Lac. After being turned into a vampire by the decadent Lestat (Tom Cruise), Louis experiences two centuries' worth of harrowing alienation and unquenchable thirst. If Pitt’s character seems especially dreary, it’s partly because the actor himself was miserable during the shoot.

38/
Columbia Pictures

#13. Moneyball (2011)

Directed by Bennett Miller

- IMDb user rating: 7.6
- Votes: 331,249
- Metascore: 87
- Runtime: 133 min

Co-produced by Pitt and co-written by Aaron Sorkin, this 2011 drama tells the true story of Oakland A’s general manager Billy Beane (Pitt). Saddled with budget constraints, Beane resorts to computer-analysis when putting together his next roster. The film earned six Academy Award nominations, including Best Actor for Pitt and Best Supporting Actor for Jonah Hill.

39/
Columbia Pictures

#12. Fury (2014)

Directed by David Ayer

- IMDb user rating: 7.6
- Votes: 388,167
- Metascore: 64
- Runtime: 134 min

Featuring Pitt as both executive producer and star, this harrowing WWII drama follows a U.S. tank commander (Pitt) and his crew into the heart of Germany. Refusing to pull any punches, director David Ayer portrays the extreme violence and brutality of battle. Beyond the bloody and mud-drenched veneer is the story of a “family in a tank.”

40/
Paramount Pictures

#11. The Big Short (2015)

Directed by Adam McKay

- IMDb user rating: 7.8
- Votes: 316,258
- Metascore: 81
- Runtime: 130 min

The 2008 financial crisis might not sound like the stuff of gripping entertainment, but director Adam McKay makes it work. Christian Bale, Steve Carell, and Ryan Gosling tackle the larger roles, while co-producer Pitt makes brief appearances as a reclusive banker named Ben Rickert. Rickert’s real-life counterpart Ben Hockett was so far off the grid that no one could find him for comment.  

41/
Warner Bros.

#10. Ocean's Eleven (2001)

Directed by Steven Soderbergh

- IMDb user rating: 7.8
- Votes: 479,609
- Metascore: 74
- Runtime: 116 min

Steven Soderbergh’s remake of a Rat Pack heist film kicked off a beloved franchise, and an endless prank war between various cast members. The first installment finds Danny Ocean (Clooney) exiting the penitentiary and enacting his grand scheme less than 24 hours later. It’s the best of the series, according to fans and critics alike. 

42/
Warner Bros.

#9. The Curious Case of Benjamin Button (2008)

Directed by David Fincher

- IMDb user rating: 7.8
- Votes: 546,375
- Metascore: 70
- Runtime: 166 min

Having previously collaborated on “Se7en” and “Fight Club,” Pitt and director David Fincher teamed up once again for this unconventional drama. Loosely based on a short story by F. Scott Fitzgerald, it depicts the trials and tribulations of a man (Pitt) who ages in reverse. The film was nominated for a whopping 13 Academy Awards—including Best Actor for Pitt—losing in all the major categories. 

43/
Morgan Creek Entertainment

#8. True Romance (1993)

Directed by Tony Scott

- IMDb user rating: 7.9
- Votes: 191,283
- Metascore: 59
- Runtime: 119 min

Written by Quentin Tarantino and directed by Tony Scott, this gritty romance centers on the misadventures of a kung-fu loving misfit (Christian Slater) and his escort girlfriend (Patricia Arquette). Pitt delivers a brief, but memorable performance as a stoner roommate named Floyd. Given the actor’s reported love of marijuana, it was probably one of his less challenging roles. 

44/
Heyday Films

#7. Once Upon a Time in Hollywood (2019)

Directed by Quentin Tarantino

- IMDb user rating: 8.0
- Votes: 181,445
- Metascore: 83
- Runtime: 161 min

Pitt and Leonardo DiCaprio earned rave reviews for their respective turns in this modern-day classic. Set in 1969 Los Angeles, it follows a fading TV actor (DiCaprio) and his stuntman (Pitt) as they navigate the shifting movie industry. Tarantino infuses both childhood memories and overarching nostalgia into the work, making it one of his most personal films to date

45/
Universal Pictures

#6. Twelve Monkeys (1995)

Directed by Terry Gilliam

- IMDb user rating: 8.0
- Votes: 544,350
- Metascore: 74
- Runtime: 129 min

By the time he was a major movie star, Pitt continued to defy convention by tackling challenging roles. Among them was the part of Jeffrey Goines in this mind-bending thriller, about a man (Bruce Willis) who travels back and forth in time. It landed Pitt his first Oscar nomination, in the category of Best Supporting Actor. 

46/
Regency Enterprises

#5. 12 Years a Slave (2013)

Directed by Steve McQueen

- IMDb user rating: 8.1
- Votes: 585,601
- Metascore: 96
- Runtime: 134 min

Brad Pitt has one Academy Award to his name, and it’s for producing this historical biopic, which tells the true story of Solomon Northup (played here by Chiwetel Ejiofor). Living as a free man in upstate New York, Northup is kidnapped and then sold into Southern slavery. Pitt appears toward the end as a Canadian laborer named Samuel Bass, who plays a vital role in procuring Northup’s freedom. 

47/
Columbia Pictures

#4. Snatch (2000)

Directed by Guy Ritchie

- IMDb user rating: 8.3
- Votes: 728,148
- Metascore: 55
- Runtime: 102 min

Playing bare-knuckle boxer Mickey O'Neil, Pitt dispenses with flying fists and an unintelligible accent in this over-stylized crime caper. As beloved now as it was upon its release, Guy Ritchie’s foremost classic sends a motley crew of gangsters in search of a stolen diamond. Entangled in the mess is O’Neil himself, who may or may not uphold his agreement to throw a major fight. 

48/
Universal Pictures

#3. Inglourious Basterds (2009)

Directed by Quentin Tarantino

- IMDb user rating: 8.3
- Votes: 1,147,271
- Metascore: 69
- Runtime: 153 min

The first collaboration between Pitt and Tarantino is considered a high point for both talents, hence its position at #88 on IMDb’s Top 250. Presenting WWII as only the director can, it follows Pitt and his crew of Jewish soldiers as they hunt for Nazis. Co-star Christoph Waltz won the Academy Award for Best Supporting Actor.   

49/
Cecchi Gori Pictures

#2. Se7en (1995)

Directed by David Fincher

- IMDb user rating: 8.6
- Votes: 1,310,884
- Metascore: 65
- Runtime: 127 min

David Fincher’s breakout film centers on a series of grisly murders, all of which revolve around the seven deadly sins. As detectives Mills (Brad Pitt) and Somerset (Morgan Freeman) search for the killer, they end up playing a role in his twisted scheme. Starring as Mills’s wife is actress Gwenyth Paltrow, who began dating Pitt soon after shooting wrapped.  

50/
Fox 2000 Pictures

#1. Fight Club (1999)

Directed by David Fincher

- IMDb user rating: 8.8
- Votes: 1,705,405
- Metascore: 66
- Runtime: 139 min

Time has been kind to David Fincher’s oft-quoted satire, which tanked at the box office before getting a second life through DVD rentals and digital streams. Now considered one of the most iconic films of the last two decades, it stars Brad Pitt as soap-making anarchist Tyler Durden. After Durden and an unnamed narrator (Edward Norton) start a fight club, it paves the way for disastrous levels of unchecked male aggression. 

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