While the concept of full-blown movie stars is sort of fading, Brad Pitt is one of the few Hollywood figures that still fits into that category. Though he has largely avoided big franchise movies, he is an actor who can still draw an audience purely on his star power and that star power is mostly due to his ability to pick roles.

Throughout his career, Pitt has shown a talent for choosing interesting projects from great filmmakers that really embrace his own talents as an actor. He has assembled an outstanding career filled with memorable characters, some who are fascinatingly off-putting and others whom the audience cannot help but fall in love with.

Jesse James - The Assassination Of Jesse James By The Coward Robert Ford (2007)

  • Available on Hoopla

Pitt doesn’t often play villains, but The Assassination of Jesse James proved he can pull off more menacing characters. Pitt plays the titular legendary outlaw in a modern Western that explores James’ celebrity which turned him into a beloved figure even though he was a cold-blooded murderer.

Pitt does a wonderful job luring the audience into this character. They are compelled by his presence at first, then repulsed by how violent and merciless he was, while also managing to find a bit of pity for the man in the end.

Tyler Durden - Fight Club (1999)

  • Available to rent on Apple TV

Tyler Durden is quite likely Pitt’s most iconic movie character, but he has also become one of the most iconic movie characters of all time. This is another example of how Pitt is able to make any character interesting to the audience even as they start to realize they are being seduced by an evil person.

Durden feels like a messiah-like figure who has all the answers and is this beacon of enlightenment in a troubled world. But soon his true colors begin to show and those answers that he has turn out to be far scarier than what the audience had in mind.

Chad Feldheimer - Burn After Reading (2008)

Pitt does not have many comedic roles on his resume, but his role as Chad in the Coen brothers’ Burn After Reading proves he can be absolutely hilarious when called upon. Chad is a fitness-obsessed trainer at a local gym who finds himself in the midst of a spy conspiracy.

Even though he’s most the most intelligent of Pitt’s characters, it is hard not to like Chad. He is like a puppy dog who just bounces around with a smile on his face and does what he’s told. But while his intentions are mostly selfless, he is quick to suggest doing a bunch of illegal stuff that puts a lot of people in danger. This is also one of the few times Pitt doesn’t look cool in a movie.

Jeffrey Goines - Twelve Monkeys (1995)

  • Available on Max Go

Pitt earned his first Oscar nomination for his role as Jeffrey Goines in the trippy sci-fi movie Twelve Monkeys. Goines is a disturbed man living in a psychiatric hospital spouting off his strange view of the world. However, he is also suspected of being responsible for a virus outbreak that destroyed society.

As the mystery unfolds, Goines is shown to be something of a disruptor, taking his activism to strange and illegal lengths, but he is also shown to be largely harmless, perhaps more misunderstood than anything.

J.D. - Thelma & Louise (1991)

  • Available on HBO, HBO Max and Max Go

Pitt’s breakout role in Hollywood came with his supporting role in Thelma & Louise. Pitt plays J.D, a handsome young bank robber who meets the two titular women on their road trip as they run from the law.

J.D. is a suave young man who seduces the unhappily married Louise and shows genuine kindness to her. However, he is also a thief who robs her of all her money. In the end, his charm gives what to the fact that he is just a self-involved punk.

Achilles - Troy (2004)

  • Available on Netflix

Troy is a rare example of Pitt going for the full-blown blockbuster movie. The swords-and-sandals epic tells the story of the Trojan War. Pitt stars as the legendary hero Achilles who helped captured the city.

Achilles is certainly an impressive warrior and proves himself to be the biggest badass on the battlefield again and again. However, he is also an arrogant and selfish man whose lack of morals is hard to cheer for. As skilled as he is in combat, there are more likable warriors in this movie.

David Mills - Se7en (1995)

David Fincher began his professional partnership with Pitt when they joined forces for the chilling thriller Se7en. Pitt plays Detective Mills, a young and arrogant cop who is investigating a series of murders that are inspired by the Seven Deadly Sins.

Mills is something of a complex hero. He is determined to stop this killer and save lives, but that doesn’t necessarily make him a good man. He seems to be a loving husband, but he can also be distant. He is a skilled investigator, but his temper makes him a problematic cop. In the end, he pays for his flaws in the thriller’s unforgettable final scene.

Cliff Booth - Once Upon A Time… In Hollywood (2019)

  • Available on Fubo TV and DIRECTV

Pitt won his first acting Oscar for his role as Cliff Booth in Quentin Tarantino’s Once Upon a Time in Hollywood. Set in the 1960s, Cliff is a Hollywood stuntman trying to make his way in the business alongside his best friend, actor Rick Dalton.

This role really shows Pitt’s movie star charisma in its finest form. Cliff is the coolest, smoothest best buddy anyone could ever ask for. But while the audience is falling in love with this guy, there are some strange things, such as his flirtation with a much younger girl and the lingering question of his wife’s death, that make one question his likability.

Louis - Interview With A Vampire (1994)

  • Available on Roku

Pitt starred in the popular vampire movie Interview with a Vampire as Louis, a plantation owner who was turned into a vampire in the 1700s. Though he is brought into the world of vampires, Louis shows that he is not willing to be as evil as some of the others.

He is shown to struggle with harming others, he seeks to help those who are in need, and he pushes back against Lestrat, the ruthless vampire who turned him. In the end, it is easy to feel sorry for such a cursed being as Louis.

Aldo Raine - Inglourious Basterds (2009)

  • Available on DIRECTV, TNT and TBS

Pitt and Tarantino clearly make a great team as they worked together to create another wonderful character with Aldo Raine in Inglorious Basterds. Set during World War II, the movie follows a group of Jewish American soldiers, led by Raine, who use brutal guerilla tactics to take down the Nazis.

It’s strange to like someone who is so gleeful about killing and torturing people, but when those people are murderous Nazis, it makes it a lot easier. Raine is also a lot of fun because he is not the typical war hero. He is a bit dim-witted and makes a blunder of his plans, yet maintains a calm and cool persona.

Ladybug - Bullet Train (2022)

  • Now in theaters

In a movie filled with deadly assassins, audiences would not expect to find someone as likable as Ladybug. Pitt gets to show off both his comedic skills and his action chops in Bullet Train as this deadly assassin who is looking to live a more peaceful life while countless people try to kill him.

It’s always fun to cheer for a hero who is cool and effective, but it is also compelling to see one who struggles. Ladybug gets hurt, is afraid, and would rather talk things out than fight. It makes for the ideal action hero for fans to root for.

Gerry Lane - World War Z (2013)

  • Available on Prime Video, Paramount+, Epix and DIRECTV

Fans might not expect to find Pitt in a zombie movie, but Gerry Lane is one of his most intelligent and heroic characters. He is a family man who is only concerned with keeping his loved ones safe when a zombie outbreak threatens the world.

He is forced to go out into the dangerous world and try to find a way to stop this outbreak. Though it is not a job Lane wants, he dedicates himself to helping as many people as he can, making quick decisions that save lives, and becoming humanity’s greatest hope.

Rusty Ryan - Ocean’s Eleven (2001)

  • Available on HBO Max

It is hard to stand out in the star-studded cast of Ocean’s Eleven but Pitt steals the show as Rusty Ryan. Rusty is one member of the iconic movie heist squad who join Danny Ocean in robbing three Las Vegas casinos simultaneously. Though Danny is the man with the plan, Rusty is the one who seems to keep the plan moving forward.

Once again, Pitt’s coolness seems effortless. Rusty never breaks a sweat and always feels totally in control, even as the situation gets hairier and hairier. He is the kind of lovable criminal that makes the audience cheer for the outlaw.

Billy Beane - Moneyball (2011)

  • Available on Hulu

Despite being a movie about baseball and statistics, the true sports drama Moneyball is an endlessly entertaining movie, even for people who are completely bored by those subjects. A lot of that has to do with the story’s central character, Billy Beane.

Billy is the manager of the Oakland Athletics baseball team which finds itself unable to compete with the richer teams who can buy up all the talent. As a result, Billy decides to use statistics to build an unorthodox winning team on the cheap. Billy’s love of the game and his willingness to play around with the rules makes for a fascinating underdog story and he is a lovable optimist worth cheering for.

Mickey O’Neil - Snatch (2000)

Despite being one of the biggest stars in the world, Pitt is known for taking supporting roles, such as his role as Mickey in Guy Ritchie’s Snatch. Mickey is an Irish con artist who happens to be a bare-knuckle boxer capable of taking his opponent out with a single punch.

Mickey’s heavy accent and fast-talking make it almost impossible to understand what he’s saying but he still has a lot of charm. Not only is he a badass, but he is also a loving son, a loyal member of his nomad community, and a lot smarter than he is given credit for.