Brad Pitt's career in Hollywood has, so far, spanned almost 35 years, during which he has blossomed from budding actor to esteemed producer. Indeed, Pitt has starred in at least 105 movies, many of which have become culturally significant blockbusters and/or cult classics. We know him from popular movies such as Flight Club, Mr. & Mrs. Smith, Seven, and Ocean’s Eleven (plus its sequels).

Interestingly, none of the aforementioned films that would be considered "Brad Pitt classics" made the list of highest-rated movies on Rotten Tomatoes. This isn't to say they weren't, of course, classics in their own right, but the movies on this list gave audiences a different side of Pitt, both as an actor and, in some cases, producer. From Once Upon a Time in Hollywood to 12 Years a Slave, here are the movies that made the cut.

8 Once Upon a Time in Hollywood (2019) — 85%

Written and directed by Quentin Tarantino, Once Upon a Time in Hollywood is a comedy drama starring an ensemble cast that includes Leonardo DiCaprio, Brad Pitt, Margot Robbie, and more. The movie centers on fading actor Rick Dalton (DiCaprio) and his stunt-double Cliff Booth (Pitt) as they struggle to navigate the rapidly changing Hollywood industry. All of this happens against the backdrop of the Tate murders orchestrated by Charles Manson and his cult. Pitt was announced to join the cast in early 2018 alongside his A-list co-stars. Earning an 85% score on Rotten Tomatoes, the film was highly praised for DiCaprio and Pitt's acting performances, so much so that Pitt won an Oscar for Best Supporting Actor in 2020.

Related: Brad Pitt's Best Action Movies, Ranked

7 Thelma & Louise (1991) — 86%

A landmark of feminist films, Thelma & Louise is a buddy road comedy-drama film directed by Ridley Scott. It stars Susan Sarandon as Louise and Geena Davis as Thelma, while Pitt plays J.D. in one of his first major film roles. The film tells the story of two best friends who embark on a road trip that quickly turns into a run from the authorities after they kill a man who attempted to rape them. Yes, Pitt is in this movie, but he shouldn't be the reason why you watch it. It's a progressive feminist tale (for its time) about strong women relationships, sitting at 86% on Rotten Tomatoes even after all these years.

6 12 Monkeys (1995) — 88%

Inspired by Chris Marker's 1962 short film La Jetée, 12 Monkeys is a science-fiction film directed by Terry Gilliam that scored 88% on Rotten Tomatoes. It stars Bruce Willis, Madeleine Stowe, and Brad Pitt in the main roles. The film tells the story of a convict James Cole (Willis), who decides to volunteer to go back in time for a mission to find out what caused the outbreak of a deadly virus. After going back in time, he gets incarcerated at a mental hospital, where he meets Jeffrey Goines (Pitt), a patient with environmentalist and anti-corporatist views. Pitt's bizarre and over-the-top performance earned him his first Academy Award nomination for Best Supporting Actor, and won him a Golden Globe.

5 The Big Short (2015) — 89%

Based on the 2010 book The Big Short: Inside the Doomsday Machine, The Big Short is a biographical comedy-drama directed by Adam McKay. With an 89% score on Rotten Tomatoes, the film stars Christian Bale, Steve Carell, Ryan Gosling, and Brad Pitt, who predict the financial crisis in the US during 2007-2008. As they conduct their research, they find out about the corruption in the system and how the crisis was caused by America's housing bubble. Pitt plays the character of Ben Rickert, a retired former trader. The Big Short was praised for its unconventional filmmaking style as the characters would often break the fourth wall to explain various finance concepts. Incidentally, it's also the first film on this list on which Pitt served as both actor and producer.

4 Inglourious Basterds (2009) — 89%

The second film on this list written and directed by Tarantino, Inglourious Basterds is a war film starring Brad Pitt, Christoph Waltz, Michael Fassbender, Mélanie Laurent, and others in the leading roles. The film provides an alternate history of two plots to assassinate Nazi Germany's leadership. One is orchestrated by 18-year-old cinema owner Shosanna Dreyfus (Laurent), whose family was executed by a German officer (Waltz) and, as result, she wants revenge. And the other group of Jewish soldiers is led by Lieutenant Aldo Raine (Pitt). Overall, the film was immensely praised by critics for its direction and performances, but it was also met with some criticism, naturally, for the historical liberties taken. Nonetheless, it scored 89% on Rotten Tomatoes.

Related: Most Iconic Roles Brad Pitt Has Ever Played, Ranked

3 True Romance (1993) — 93%

Directed by Tony Scott and written by Tarantino, True Romance is a romantic crime film starring an ensemble cast led by Christian Slater and Patricia Arquette. These actors portray newlyweds who are on the run from the Mafia after stealing a shipment of cocaine. In one of his earlier film roles, Pitt plays the small supporting role of Floyd, a stoner who helps police locate the place of the final deal. Although it was considered a box office failure at first, it has since grown a cult following and was declared as one of the best American movies of the 1990s. It sits at 93% on Rotten Tomatoes.

2 Moneyball (2011) 94%

Based on the 2003 nonfiction book of the same name, Moneyball is a sports drama film directed Bennett Miller and produced by Pitt himself. It stars Pitt as the Oakland Athletics baseball team's general manager Billy Beane and Jonah Hill as the assistant general manager Peter Brand. It tells the story of how the two put together a baseball team in 2002 against a limited budget and with only undervalued players to choose from. The film garnered critical praise for the screenplay and acting performances, especially Pitt's, who was nominated for Best Actor at the Academy Awards. It scored 94% on Rotten Tomatoes.

1 12 Years a Slave (2013) — 95%

Last but not least, based on the 1853 memoir Twelve Years a Slave by Solomon Northup, the movie of the same name is biographical drama film directed by Steve McQueen. It tells the heartbreaking story of free African-American man Solomon Northup (Chiwetel Ejiofor) who is promised a job in Washington D.C, but instead gets sold into slavery for 12 years, during which he was made to work on plantations. As for Pitt, he plays the character of Samuel Bass, an abolitionist who helped Northup attain his freedom. McQueen was the first Black British producer and director to win Best Picture at the Academy Awards (via THR). Sitting at 95% on Rotten Tomatoes, this is Pitt's highest-rated movie on the aggregator website.