Brad Pitt has had an illustrious acting career. He has been working in film for four decades, and despite his recent comments about how he plans to retire soon, there seems to be no end in sight for him. With upcoming projects like Babylon and an unnamed George Clooney film, he is still in his prime.
Pitt is not only an Academy Award-winning actor, though. He is also a prestigious producer, the owner of a wildly successful production company, and one of the most chaotic character actors to have ever been trapped inside a movie star's body. While he made waves in the film industry because of his good looks, he is no stranger to playing some of the most outrageous characters in cinema. With the release of Bullet Train on the horizon, Pitt will add another rambunctiously chaotic character to his bedlam of films.
Ladybug, 'Bullet Train' (2022)
Everything about David Leitch's films screams action-packed and escapist. With movies like John Wick and Deadpool 2 under his belt, his newest foray into the action thriller genre is Bullet Train, a high-octane ride on an assassin-filled bullet train. The trailer shows an ensemble cast filled with Pitt, Sandra Bullock, and Aaron Taylor-Johnson having to fight for survival on a train with limited stops.
Pitt's role as Ladybug might just be one of his most deranged – filled with bloody fight scenes at high speeds, snappy humor, and a total existential crisis. All happening while not being able to take a breather. Seeing Pitt's unhinged character race his way through a train to stay alive is enough to cause whiplash.
Tyler Durden, 'Fight Club' (1999)
Fight Club's Tyler Durden is the best character in Pitt's career. Tyler Durden birthed a movement of rebellion and a revolt against the normal, the mundane, and the capitalistic society that disenfranchises us all. He is the sick and twisted part of the Narrator's subconscious who comes out to play as he slips into heavy insomnia.
Pitt's most well-known role is filled with fighting, terrorizing communities, and becoming a menace larger than himself with the out-of-control Project Mayhem. One of the most chaotic scenes in the entire movie is when the owner of the bar where Fight Club takes place comes for a chat. Tyler scares the man away with his maniacal pleadings to be beat, bloody and broken, into the ground.
Early Grayce, 'Kalifornia' (1993)
In one of Pitt's earliest roles, Kalifornia puts the actor in the role of a serial killer. The film follows a writer and his girlfriend while they're working on a book about serial killers. The two plan a trip across the U.S. to document famous murderers and end up ride-sharing with Pitt's character.
However, they don't know that Pitt's character, Early, is in the middle of his own serial-killing spree. They must later fight to survive once he turns on them. The role is very different from most of Pitt's later ones. As Early, he has black hair and facial hair that rivals Grizzly Adams, only adding to his convicted killer mentality.
Aldo Raine, 'Inglourious Basterds' (2009)
Brad Pitt stole the screen in every scene that he was in as Aldo Raine in Inglourious Basterds. Aldo is the brutal and apathetically cruel Nazi-killing Lieutenant in Quentin Tarantino's ode to revenge. Tarantino is no stranger to bloody violence, but Pitt's character took things even further.
Lt. Aldo Raine assembles a team of Jewish soldiers to commit heinous acts of violence against Nazis, including scalping them. The movie showed a new side to Pitt, as he is seldom in such violent films. Inglourious Basterds even had the movie star yelling things like “And all y'all will git me one hundred Nazi scalps, taken from the heads of one hundred dead Nazis. Or you will die tryin'."
Floyd, 'True Romance' (1993)
True Romance is the Tony Scott cult classic that follows comic book nerd Clarence and the sex worker Alabama as they fall in love. Clarence ends up killing Alabama's pimp when he tells him they have fallen in love, and the two hit the road for California.
Many people hardly remember Pitt being in the movie. He played a small but memorable, role as Clarence's stoner roommate, Floyd. He looks all the part of a sluggish, deadbeat roommate with long, greasy hair and sweatpants. He can be seen with a bag of Fritos sitting on a couch – quite the opposite of any other Brad Pitt role.
Jerry, 'The Mexican' (2001)
The Mexican involves a cursed pistol, a mob kidnapping, and a lot of chaos on the way to Mexico. The movie stars Brad Pitt, Julia Roberts, and James Gandolfini and follows a down-and-out couple after Jerry is sent on one last mob job. Jerry is given an ultimatum by his mob boss: either go to Mexico to retrieve a priceless antique pistol or suffer some heavy consequences.
Jerry is very selfish, so he makes his way down to Mexico against his partner's wishes. He finds himself in horrible predicaments involving shootouts, stealing cars, and arrests. Pitt plays the role beautifully, though, and this was one of the first times that his comedic talents were put on display.
Jackie Cogan, 'Killing Them Softly' (2012)
The monologue at the end of Killing Them Softly by Brad Pitt's character is the most memorable part of the entire movie. With his disdain for Thomas Jefferson's words dripping from his every word, he speaks volumes with, “America’s not a country. It’s a business. Now fucking pay me,” before the screen cuts to black.
The movie follows a bunch of rival crooks who plan to rob a mob's card game and the incompetence that comes with it. Pitt comes into the movie as Jackie Cogan, a mob enforcer whose one job is to eradicate those responsible for the plan. Pitt kills in the role with smooth-talking and an even smoother style, with slicked-back hair and an ever-present weapon.
Jeffrey Goines, 'Twelve Monkeys' (1995)
In Pitt's turn as a disturbed rich kid in Terry Gilliam's Twelve Monkeys, he earned his first Academy Award nomination. And unhinged he was. Pitt played Jeffrey Goines, a cockeyed weirdo who is part of the asylum in which Bruce Willis' character ends up.
Pitt completely engulfed himself in the part, looking crazed in the eyes in every scene and completely transforming himself into a man filled with manic energy. Nearly every one of his scenes shows off a deranged look in his eyes, even when he eventually plays the role of the dutiful son in the latter half of the movie.
Cliff Booth, 'Once Upon a Time... In Hollywood' (2019)
Tarantino's 2019 classic follows a moment in Hollywood history with an alternative narrative that, of course, takes revenge on the bad guys. The movie is filled with 60s sunshine, and Brad Pitt, Leonardo DiCaprio, and Margot Robbie bring their characters to life so well that it's hard not to fall in love with them.
In particular, Pitt's Cliff Booth is a character's roller coaster ride. He is the easy-going and mysterious stunt double to DiCaprio's Rick Dalton, with a sick sense of late-60s style. In the movie, there is a lot of talk about how mad Cliff Booth is, with rumors of him killing his wife. And his madness finally makes a full appearance at the end when he smokes a cigarette laced with acid and fights off all of Charles Manson's murderous cult members.
Mickey O'Neil, 'Snatch' (2000)
Brad Pitt was notoriously nervous about his Irish accent while playing the role of Mickey in Guy Ritchie's Snatch. It's one of the few movies that he's in where he explores one. Despite this, Pitt played the goofy and methodical Mickey perfectly.
In the movie, an illegal boxing promoter convinces a gangster to offer bets on the bare-knuckle boxer, Mickey O'Neil. When Mickey doesn't throw his first fight as agreed, another match is demanded of him. Pitt perfectly encapsulated the interesting young man who never seems to care about all the trouble he causes other people.