Pitt’s natural charisma, handsome looks, and talent are all on display in his breakout role as J.D. in Ridley Scott's adventure crime drama, Thelma & Louise. He appears as a charming grifter who seduces Thelma (Geena Davis) with his charm and a smile. Pitt made the most of a supporting role, something he has become even more adept at throughout his career. It’s a performance that lets everyone know that here is an actor who was born to be a superstar. The audience saw him holding a hair dryer and wearing a cowboy hat and knew right away, "Yeah, this guy’s going places."

Neil Jordan's Interview With the Vampire: The Vampire Chronicles is one of two movies that helped make Pitt an A-list leading man. Paired with a wonderfully antagonistic Tom Cruise as Lestat, Pitt is the softer, more sensitive vampire Louis who gives the titular interview. He details his life before and after becoming a creature of the night, all while remaining alluring to the viewer (and interviewer). That gentleness, in spite of being an actual monster, boosted Pitt’s profile, making fans swoon.

The other movie that cemented Pitt's status as leading man is the sweeping Edward Zwick drama Legends of the Fall. Pitt stars as one of three brothers torn apart by multiple tragic circumstances after serving in World War I and working through Prohibition. Anthony Hopkins plays the family patriarch, and Pitt holds his own against the acting legend in an excellent dramatic performance as Tristan, the middle son with a wild streak.  

After a run of more romantic leading roles, Pitt showcased his versatility with a hard turn into darkness with Se7en. Working with director David Fincher for the first time, Pitt plays Detective David Mills, a somewhat hot-tempered idealist opposite Morgan Freeman’s near retirement Detective William Somerset, as they investigate a series of brutal murders inspired by the Bible’s seven deadly sins. Pitt gives a grounded, powerful performance, culminating in the film’s infamously grim ending.

Once again, Pitt makes the most out of a supporting role, this time going against type as an institutionalized radical who might be responsible for a deadly outbreak in 12 Monkeys. He plays the role of Jeffrey Goines with an intense, erratic energy, unlike anything he’d done in his career to that point, and his efforts earned him his first Oscar nomination for Best Supporting Actor. Director Terry Gilliam has his twisted sense of humor woven throughout the otherwise dark material, and Pitt picks up on that energy and runs with it, to a memorable performance which lets the audience understand that he has plenty of range.

We're going to have to break the first two rules of Fight Club, and talk about Fight Club. Reuniting with David Fincher, Pitt delivers arguably his most essential role as Tyler Durden, the leader of the titular Fight Club. Tyler is masculine, cool, smooth with women, unburdened and unbothered — in other words, someone like the movie star persona of Brad Pitt. But the film is critical of those ideals, satirizing violence and toxic masculinity, and delivering an iconic twist. Pitt nails every single element of the performance, utilizing his own image to play up themes that remain relevant to this day.

Pitt fits in well with the frenetic energy of Guy Ritchie’s gangster flick Snatch, even if no one can fully understand his Irish gypsy accent. He plays Mickey O’Neil, a seemingly dimwitted underground boxer, who handles any takers with his fists, and becomes entangled in the complicated crime plot led by Jason Statham’s career criminal Turkish. It was an unexpected choice for both Pitt and Ritchie, but the gamble paid off with a highly entertaining performance.

The essence of cool just might be contained in this 2001 remake from director Steven Soderbergh. Co-leading what amounts to a modern-day Rat Pack alongside George Clooney, Pitt's unflappable Rusty Ryan has to be the world’s chillest thief, notably eating in almost every scene that he’s in to subtle, but unquestionably great, comedic effect. Pitt takes a slight backseat to Clooney's Danny Ocean, who’s focused not only on robbing the casinos but also on getting the girl (Julia Roberts), but Rusty is no less a leader of this memorable crew. Pitt reprised his role in 2004's Ocean's Twelve and 2007's Ocean's Thirteen.

Loosely based on legendary Greek author Homer's The Iliad, Wolfgang Petersen's historical epic Troy showcases Pitt's most action hero physique. He commandingly plays the mighty Achilles, leading the battle and sacking of Troy, minus the fantastical mythological elements. Troy is a classic Hollywood sword-and-sandal epic, with an incredible production and packed with an all-star cast which includes Orlando Bloom, Eric Bana, Diane Kruger, Brian Cox, Julie Christie, and the late, great Peter O’Toole.

This Doug Liman action-comedy gets both the action and the comedy just right. Pitt and Angelina Jolie play John and Jane Smith, a bored married couple who are, in fact, secret assassins for competing agencies. Their chemistry is undeniable, even when the two highly skilled assassins are in the middle of trying to kill one another in the film's thrilling action sequences.

Jesse James was an iconic figure, a celebrity long before the world at large would really understand what that means, so it’s only fitting that a massive star like Pitt portrayed this American outlaw. Casey Affleck plays the titular coward Robert Ford, who is obsessed with Pitt’s enigmatic bank and train robber, pursuing him until he is ultimately disappointed when the man doesn’t meet the myth. Pitt is perfectly understated in the role, an icon playing an icon with nuance and depth.

Andrew Dominik's biographical crime drama earned two Oscar nominations, one for Best Cinematography for Roger Deakins' stunning work, and one for Best Supporting Actor for Affleck. Of all the films he has been a part of, this is one of Pitt's personal favorites.

Pitt’s third outing with Fincher earned him his second Oscar nomination, this time in the leading actor category. The Curious Case of Benjamin Button is at once tragic and romantic, with Benjamin beginning his life as a miniature old man physically, and growing into a handsome man in his prime, and then, continuing to age backwards as he ages. It’s a testament to Pitt’s unique skills that he seamlessly blends the physical and mental ages of his extraordinarily unusual character.

This magnum opus, co-starring Cate Blanchett, Taraji P. Henson, Tilda Swinton, Julia Ormond, Jason Flemyng, Mahershala Ali and Elias Koteas, earned a whopping 13 Oscar nominations, winning Oscars for its breathtaking Visual Effects, Makeup, and Production Design.

Inglourious Basterds is Quentin Tarantino’s far from historically accurate but absolutely enthralling look at World War II, and the eventual downfall of Hitler, thanks in part to the power of cinema. Despite the serious subject matter, Tarantino’s humor is on display, and expertly delivered by Pitt. He plays Lt. Aldo Raine, a Tennessee-born Nazi fighter with a distinct Smoky Mountain twang. He is the leader of the Basterds, a group of soldiers who are in Nazi occupied France to inflict terror on Nazis. Lt. Aldo Raine helps to orchestrate the film’s satisfying final vengeance against Col. Hans Landa (an equally incredible and ultimately Oscar-winning (for Best Supporting Actor) Christoph Waltz).

Bennett Miller's Moneyball tells the story of legendary sports manager Billy Beane, who revolutionized baseball strategy after being considered a failure as a player. It’s an underdog tale, and Pitt is compassionate, empathetic, and charming as he leads his team to success. With this baseball movie, Pitt scored a double himself: Receiving two Oscar nominations for his work on the film, one for Best Picture and another for Best Actor.

Pitt reunited with Tarantino for his Oscar-winning performance as stuntman Cliff Booth in this alt history drama about the twilight of the golden age of Hollywood. Fading star Rick Dalton (Leonardo DiCaprio) struggles to make peace with the fact that he isn't burning as bright as he once was, while Cliff tries to help him see that he's still got it. All the while, the threat of radicalized hippies and the fate of actress Sharon Tate (as played by Margot Robbie) looms in the background.

Once Upon A Time… In Hollywood, which also stars Al Pacino, Kurt Russell, Timothy Olyphant, Margaret Qualley, Bruce Dern, and the late, great Luke Perry, was nominated for 10 Oscars, including Best Picture and Best Director. In addition to Pitt winning for his performance, the film won another Oscar for its Production Design.