Since breaking through in the early 1990s, Brad Pitt has enjoyed a long and successful career as one of Hollywood’s true movie stars, and there have been some important milestones on his journey to the top. Pitt has a remarkable range as an actor. His good looks and abundant charm mark him out as natural leading man material, but he has a variety of quirky roles which display his ability to disappear into his characters.

Pitt has worked with some of the greatest directors of the modern era, including David Fincher, Quentin Tarantino and Ridley Scott. This has helped him compile an impressive filmography consisting of movies in many different genres. Among these movies, a few have marked important milestones in his career. Without massive hits like Fight Club and Ocean’s Eleven, and impressive acting showcases like The Curious Case of Benjamin Button and 12 Monkeys, Pitt wouldn’t have made it to where he is today.

Brad Pitt’s Oscar Nominations For Acting

Movie
Role

12 Monkeys (1995)
Jeffrey Goines

The Curious Case of Bejamin Button (2008)
Benjamin Button

Moneyball (2011)

Once Upon a Time in Hollywood (2019) – WON
Cliff Booth

10Thelma And Louise (1991)

Ridley Scott gave Brad Pitt his breakthrough role

It was inevitable that he would step into the spotlight, but Pitt could easily have built himself a career as a character actor based on the evidence of Thelma and Louise.

Brad Pitt’s first big breakthrough in the film industry was in Ridley Scott’s feminist road trip movie Thelma and Louise. Susan Sarandon and Geena Davis star as two friends who embark on a vacation away from the men in their lives, but their road trip takes a dark turn when they are forced to kill a man in self-defense at a roadside bar. Brad Pitt plays a cowboy hitchhiker with a criminal background who runs into the two women at a gas station.

Thelma and Louise is one of Ridley Scott’s best movies, even though he’s perhaps more famous for high-concept sci-fi stories and epic historical dramas. Brad Pitt is key to the movie’s allure, even though he only plays a supporting role. His good looks and inimitable charm are on full display at such an early stage of his career. It was inevitable that he would step into the spotlight, but Pitt could easily have built himself a career as a character actor based on the evidence of Thelma and Louise.

9Seven (1995)

Brad Pitt’s first collaboration with David Fincher established his caliber as a leading man

Pitt had played leading roles before, in A River Runs Through It and Legends of the Fall, for example, but Seven was his first massive hit.

Pairing up with Morgan Freeman just a year after The Shawshank Redemption would be a tall order for any actor, but Brad Pitt showed that he was more than capable of matching the biggest stars in Hollywood. Seven (also frequently stylized as Se7en) is a twisty crime thriller that features Pitt and Freeman following the tracks of a serial killer who uses the biblical seven deadly sins as motivation for his elaborate murders.

Pitt had played leading roles before, in A River Runs Through It and Legends of the Fall, for example, but Seven was his first massive hit. It remains a classic for fans of murder mysteries almost 30 years later. Seven’s unforgettable twist ending put the cherry on top of Pitt’s superb performance as a volatile rookie detective. It also provided him with one of his most famous film quotes: “What’s in the box?”

812 Monkeys (1995)

Brad Pitt got his first Oscar nomination for Terry Gilliam’s sci-fi thriller

Brad Pitt earned his first Oscar nomination for his portrayal of Jeffrey Goines, and his manic energy ensures that his scenes stand out.

In the same year he starred in Seven, Brad Pitt also played a supporting role in 12 Monkeys alongside Bruce Willis. Directed by Terry Gilliam, 12 Monkeys is a cerebral time-travel thriller that uses a virus outbreak as an allegory for global climate change. Willis plays a prisoner who is sent back in time by a group of scientists to prevent a catastrophic pandemic. Pitt plays a patient at a mental hospital who has more to do with the pandemic than first meets the eye.

Brad Pitt earned his first Oscar nomination for his portrayal of Jeffrey Goines, and his manic energy ensures that his scenes stand out. Pitt infuses his environmental, anti-capitalist ramblings with a lot of humor, and Gilliam’s direction is also a big help. Gilliam fills the backgrounds of Pitt’s scenes with vibrant, nonsensical action, which creates a more disorienting feeling. Willis plays off him expertly, a stoic and immovable object against Pitt’s unstoppable force.

7Fight Club (1999)

Possibly Brad Pitt’s most iconic role

Fight Club is famous for its rules, its brilliant twist ending, and frankly, Brad Pitt taking his shirt off.

Brad Pitt was an established star before Fight Club, but he became a sensation among film fans for his electric role as Tyler Durden. Pitt’s charisma kicks into overdrive for Fight Club, in which he plays the confident and ambitious opposite to Edward Norton’s gray-faced narrator. Together, the duo start an underground fight club which develops from a cathartic outlet for lost souls into a cult with its eyes set on dismantling the corporate power structures of Western society.

Fight Club is famous for its rules, its brilliant twist ending, and frankly, Brad Pitt taking his shirt off. However, his performance is notable for much more than just the time he spent in the gym beforehand. Like in 12 Monkeys, he plays an anti-authoritarian wildcard who sees things in his own way and isn’t afraid to point them out. His performance showcases his ability to command the entire screen with his presence. It helps that David Fincher’s direction is dialed in to his every movement.

6Ocean’s Eleven (2001)

Brad Pitt and George Clooney kicked off a trilogy in style

The original Ocean’s 11 starred Frank Sinatra, Sammy Davis Jr. and Dean Martin, but the remake pulls off the near-impossible task of surpassing it in terms of style.

The original Ocean’s 11 starred Frank Sinatra, Sammy Davis Jr. and Dean Martin, but the remake pulls off the near-impossible task of surpassing it in terms of style. Ocean’s Eleven is one of the best heist movies of all time, thanks to a charming ensemble cast working together beautifully, and Brad Pitt and George Clooney are at the forefront of the gang’s every move. The two old friends team up to pull an elaborate heist on three Las Vegas casinos in one night.

Pitt plays Rusty Ryan, Danny Ocean’s second-in-command, who helps corral their eclectic team and train them for the big occasion. When Danny is emotional, Rusty is logical. When Danny is hasty, Rusty has the wisdom to take a step back and see the bigger picture. Pitt embodies cool as Rusty, strolling around his lavish surroundings with a cheeseburger or a soda in hand, acting like he’s already the richest man in Vegas.

5Mr. & Mrs. Smith (2005)

Brad Pitt’s personal and professional lives became entwined in his action thriller with Angelina Jolie

Pitt began a relationship with Angelina Jolie on the set of Mr. & Mrs. Smith, and the two became an iconic Hollywood power couple.

By the mid 2000s, Brad Pitt was a Hollywood A-lister with paparazzi following his every move. He began a relationship with Angelina Jolie on the set of Mr. & Mrs. Smith, and the two became an iconic Hollywood power couple. Actors can find it hard to connect with audiences once they reach a certain level of stardom, but Pitt plays such a variety of roles that he rarely has that problem.

Mr. & Mrs. Smith is a fun action thriller about two globe-trotting assassins who keep their identities secret from each other during their marriage. It mixes huge action sequences with some great comedy and plenty of sex appeal. The movie wouldn’t work without Pitt and Jolie sharing such compelling chemistry. Mr. & Mrs. Smith was recently rebooted as an Amazon Prime Video series starring Donald Glover and Maya Erskine, although it’s a much different prospect.

4The Curious Case Of Benjamin Button (2008)

One of Brad Pitt’s most challenging roles earned him glowing reviews

Pitt is known for extravagant performances, but The Curious Case of Benjamin Button shows that he doesn’t just coast on charm.

The Curious Case of Benjamin Button is based on a short story by F. Scott Fitzgerald. It follows a man who is born with the appearance and the physical ailments of an old man. Over the course of the 20th century he ages in reverse, and Brad Pitt plays him at all stages of his life, thanks to some remarkable makeup and visual effects. It’s the kind of role that seems designed to showcase an actor’s range, and Pitt rose to the challenge.

Working with David Fincher once more, Brad Pitt delivered one of the finest performances of his career, and the movie required him to. The Curious Case of Benjamin Button could easily fall flat with a less compelling actor in the lead role. Cate Blanchett and Taraji P. Henson also put in some fantastic work. Pitt is known for extravagant performances, but The Curious Case of Benjamin Button shows that he doesn’t just coast on charm.

3Moneyball (2011)

Brad Pitt has developed a career as a producer as well as an actor

Moneyball is a sports movie that can be enjoyed by people with no interest in baseball. It’s a drama about conflicting ideologies in a highly competitive industry.

Although most people know Brad Pitt as an actor, the second half of his career has seen him working more and more frequently as a producer. He stars in some of this movies, but not all of them. His production company, Plan B Entertainment, has worked on The Departed, 12 Years a Slave and Moonlight, all of which won Best Picture. In fact, Pitt’s first Oscar win was for 12 Years a Slave, not as an actor but as a producer.

Moneyball earned Pitt Oscar nominations for both Best Actor and Best Director.Moneyball tells the true story of the Oakland Athletics during the 2002 season. Pitt plays general manager Billy Beane, who worked to implement a more analytical approach to player recruitment and other big franchise decisions. Moneyball is a sports movie that can be enjoyed by people with no interest in baseball. It’s a drama about conflicting ideologies in a highly competitive industry, and it benefits from a superb script by Aaron Sorkin and Steven Zaillian.

2The Big Short (2015)

As part of an ensemble cast, Pitt made a huge hit out of a complicated story

An actor of his stature can take his pick of roles, but Pitt repeatedly shows a desire to work on inventive, important dramas rather than safer bets.

The Big Short is based on a non-fiction book by Michael Lewis which offers an inside look at the 2007-2008 financial crisis from a few different angles. The Big Short makes some slight alterations to the true story, but it’s an interesting blend of entertainment and education. The characters often break the fourth wall to explain some of the more technical terms or the relevant context, but the movie never loses sight of its compelling plot.

Brad Pitt is just one part of an impressive ensemble cast that also includes Ryan Gosling, Steve Carell and Christian Bale. Still, Pitt plays a vital role. An actor of his stature can take his pick of roles, especially since he has his own influential production company, but Pitt repeatedly shows a desire to work on inventive, important dramas rather than safer bets like taking a role within a pre-existing franchise.

1Once Upon A Time In Hollywood (2019)

Brad Pitt earned his first acting Oscar alongside Leonardo DiCaprio

With Once Upon a Time in Hollywood, Tarantino puts DiCaprio and Pitt in the same rarefied air as legends of Hollywood’s past such as Bruce Lee and Steve McQueen.

Brad Pitt had already starred in Inglourious Basterds when Quentin Tarantino called on him again for his love letter to New Hollywood, and Once Upon a Time in Hollywood gave him an even more central role. Pitt plays Cliff Booth, the rugged stunt double to Leonardo DiCaprio’s character, the washed-up actor Rick Dalton. As the two struggle to make their way back to the top, the threat of the Manson family looms in the background.

With Once Upon a Time in Hollywood, Tarantino puts DiCaprio and Pitt in the same rarefied air as legends of Hollywood’s past such as Bruce Lee and Steve McQueen. In an era of cinema with fewer bankable stars, Pitt is one of very few with old-school power. His stylish performance earned him his first Oscar for acting on his fourth nomination. Brad Pitt has been cast in Tarantino’s next movie, The Movie Critic, which the director claims will be his last.