The 20 most memorable Brad Pitt roles

Pitt had been in movies before “Thelma & Louise,” but they were small roles in forgotten films. Then Ridley Scott’s movie came out and Pitt grabbed people’s attention. The cultural legacy of “Thelma & Louise” is two things. One, the famous ending. Two, people remembering the handsome, charismatic young man playing the drifter J.D.

“Cool World” is now an infamous movie, but it’s a cult one at best. With “Thelma & Louise,” Pitt popped, but was it just because the good-looking guy with a winning personality was playing, you know, a good-looking guy with a winning personality? “True Romance,” directed by Ridley's late brother Tony, has some notable small roles. Gary Oldman is certainly making some choices. Pitt once again grabbed attention, but this time he was playing Floyd, a scruffy, stupid stoner. He showed he can act, and be funny at that.

Before “Twilight” was a thing, Anne Rice was the queen of “romantic vampires.” There has always been a strain of vampire stories about their sexy allure, and Rice just made that overt. “Interview with the Vampire” is her most famous story, and this is the most famous adaptation of her work. Tom Cruise plays the vampire Lestat, Rice’s most iconic character, but Pitt is right there as Louis as well.

We will say this, knowing we’re in the minority: “Se7en” is bad. Like, really bad. It’s gross and empty-headed but thinks it’s smart. That being said, it was a hit, and it’s a movie many people consider a favorite. It’s definitely one of the Pitt movies people think of the most. Plus, there’s the “What’s in the box!?!?” of it all.

Of Pitt’s 1995 movies, “Se7en” was the bigger hit, and probably had a bigger impact on Pitt’s career, since he became a movie star. That being said, “Twelve Monkeys” is a better movie, and was significant in Pitt’s career as well. Bruce Willis is the star of this dystopian sci-fi film, but Pitt has the showiest part. For this movie, Pitt received his first Oscar nomination, for Best Supporting Actor.

“Meet Joe Black” is one of those movies most people have heard of, and most people remember, but most of those people have also never seen it. That being said, Pitt being in “Meet Joe Black” is well-remembered, and the internet has helped. A scene from that film became viral. Rightfully so, by the way. It is bananas.

Perhaps the most polarizing of Pitt’s movies. As often is the case in such circumstances, we may disappoint by falling somewhere in the middle. “Fight Club” is fine. Pretty good, even. It’s flawed, sure, but it has some good moments to it. Pitt certainly pops as Tyler Durden, with David Fincher weaponizing Pitt’s charm and good looks with skill. It’s a major cult favorite, so it definitely is a memorable Pitt movie. Maybe even the most memorable?

Pitt has long been a movie star, and is not afraid to make a down-the-middle big-budget movie. However, he has esoteric tastes and isn’t just out there looking to make money being handsome on the big screen. Guy Ritchie’s first feature film, “Lock, Stock, and Two Smoking Barrels” got him some attention, including Pitt’s. He lent his acting skills, but also his name and face for the marketing, to Ritchie’s follow-up “Snatch.” While Pitt is just a piece of an ensemble, “Snatch” solidified Ritchie’s career, and Pitt played a role in that.

We’ll let this one stand in for the full “Ocean’s” trilogy. It was a major success in the 2000s. The “Ocean’s” films were built on celebrity and fame. Pitt was right up there with George Clooney and Julia Roberts on that front. This franchise is also a classic example of the “Brad Pitt eating in movies” meme. All told, “Ocean’s 11” is the best of the bunch.

Though “Troy” is a mixed bag of a movie, the sword-and-sandals epic made almost $500 million back in 2004, so it made a splash. Mostly, people wanted to see Pitt in a historical drama. He played Achilles alongside Eric Bana as Hector and Orlando Bloom as Paris. In the story of “The Iliad,” there are two roles that are best remembered: Helen of Troy and Achilles. Pitt played one of them. Probably could have pulled double duty if called upon, to be honest.

In terms of “most memorable,” “Mr. and Mrs. Smith” probably wins. Most of that has nothing to do with the film itself, though. The movie is a solid enough action-comedy that made a lot of money. It would be on this list regardless. However, “Mr. and Mrs. Smith” is the movie where Brad Pitt and Angelina Jolie became “Brad Pitt and Angelina Jolie.” A thousand tabloid stories were born, and one of the most famous pairings in celebrity media came to the forefront.

While “Burn After Reading” isn’t a totemic Coen Brothers movie, it’s an underrated offering in their filmography. The movie features a couple of staples of their films, George Clooney and Frances McDormand, but Pitt popped in to have his Coen experience. Pitt has the showiest role in the film, one he handles with aplomb. It’s why he was the focal point of the trailer, even if (spoiler adjacent) he’s not as large of a role in the movie itself.

“Benjamin Button” is a decidedly different movie from “Fight Club,” but it’s equally polarizing. Some love it, while others find it silly or, even more damning, boring. Pitt plays a man who ages backward in this slice of American Magical Realism. However, it was an Oscar player, and Pitt earned his first Best Actor nomination.

Pitt was certainly not a Quentin Tarantino reclamation project in “Inglourious Basterds.” He’s the face of the movie that probably helped get audiences interested. Now, Christoph Waltz ended up stealing the show, and winning an Oscar. The movie was a hit, though, and may honestly be Tarantino’s best movie. Pitt’s hamming it up a bit, but not in a bad way. Also, this isn’t exactly a subtle movie (to its credit).

We certainly did not envision a movie about a baseball executive using statistical analysis to help his underfunded team win becoming a totemic film of the 2010s. And yet, here we are. “Moneyball” was a solid hit, but it has become a cable staple and a beloved Pitt role. Some have even said his turn as Billy Beane, GM of the Oakland Athletics, is his best work. Well, he did get another Best Actor nomination.

After “Moneyball,” there’s a sizable stretch of time where Pitt either starred in smaller, grittier movies, or had secondary roles in medium-sized films. Also, he was doing a lot more producing. “World War Z” stands out as anomalous, a big-budget blockbuster of a zombie movie. It’s a good film, headier than you may think, though with plenty of violence and zombie gore as well. Also, it was a bigger hit than you may remember. “World War Z” brought in $540 million worldwide.

“By the Sea” is a small film, and it’s forgotten by many. However, it certainly has its memorable place in terms of celebrity lore. This was the last big “Brad Pitt and Angelina Jolie” moment in terms of popular culture. They shot the movie together on their honeymoon. They produced it together, and Jolie wrote the screenplay and directed it. She had herself credited as “Angelina Jolie Pitt” on the film! Maybe “By the Sea” was when the tide turned on them as a celebrity couple, and the clock did end up ticking not long after. Pitt and Jolie divorced in 2019.

“The Big Short” is a good movie that captured the financial malfeasance at the heart of the 2008 economic crisis in America well. Pitt is but one piece in the film, but “The Big Short” was an Oscar play and is a time capsule of some value. It’s also a little of a “What have we done?” moment. Adam McKay had been directing big, dumb comedy movies, but he took a swing here at a political dramedy and we welcomed it with open arms. He pivoted his entire career and gave us the unremarkable “Vice” and disastrous “Don’t Look Up.” While “The Big Short” earned its merits, maybe we would have been better off not validating him.

Finally, Pitt won his Oscar. Deservingly, too. Reuniting with Tarantino, Pitt played Cliff Booth, the stunt double and majordomo of Leonardo DiCaprio’s former acting star Rick Dalton. Unsurprisingly for Tarantino, it’s a lovingly crafted look at a bygone era of Hollywood, but also there’s a lot of violence and some shots of women’s feet that seem almost confrontational. After this one, though, Pitt was officially an Oscar winner.

We’ll be honest, it felt like ending with a 2019 film was going to leave us a little too far in the past for Brad Pitt, but since then he hasn’t served us up many options. Mostly he’s been producing. We like “Ad Astra” and “Babylon,” but neither was a hit, and “Babylon” in particular died a thousand deaths in theaters. The less said about “Wolfs” the better. It’s too early to say anything about “F1.” “Bullet Train” is the only one left standing. It’s a reasonably fun action-comedy that Pitt seems to be enjoying himself in. By dint of making almost $300 million, it’s his biggest hit of this time frame. Maybe even Pitt isn’t immune to ebbs and flows in movie stardom.