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Brad Pitt as Cliff Booth in Once Upon a Time... In Hollywood

He is Brad freakin’ Pitt, and he never forgets it. It is that confidence that helped Brad Pitt earn his first acting Oscar (Best Supporting Actor) for playing stuntman Cliff Booth in Once Upon a Time In Hollywood, which is easily one of the most badass roles of his career.

In fact, the 56-year-old, who had previously received an Academy Award for producing the Best Picture winner 12 Years a Slave in 2013, has played quite a few badasses (in various senses of the word) throughout the years. It is why, even at a time when he is technically a veteran of the industry, Brad Pitt is still sought out to play roles like a bold space explorer in Ad Astra, a World War II tank commander in Fury, and an invisible vigilante in Deadpool 2.

Yet those are only a couple of the notable characters that have made Brad Pitt one of the most badass actors alive. If you want to hear about more, I have 11 right below here, ranked by badassness.

Brad Pitt in Mr. & Mrs. Smith

11. John Smith (Mr. & Mrs. Smith)

World class secret agent. Deadly assassin. Devoted suburban husband. These are the lives that John Smith, while not privy to the fact that his wife, Jane (Angelina Jolie, who would eventually become his real-life spouse) has the same job and he is her next target. Coincidentally, she is his.

Directed by Edge of Tomorrow helmer Doug Liman from a screenplay by Simon Kinberg, Mr. & Mrs. Smith, is a fun, heartwarming romantic comedy about a strained marriage given a second chance when they realize their failure to kill each other must mean that they are made for each other. Shout out to Brad Pitt, and Angelina Jolie, too, of course, for doing what they do best: making such a despicable occupation look so effortlessly cool.

Brad Pitt in World War Z

10. Gerry Lane (World War Z)

What sets author Max Brooks’ acclaimed oral history of a global zombie outbreak apart from other stories of reanimated, flesh-eating corpses is that World War Z plays out more like a geo-political thriller than an action/horror hybrid. Star and producer Brad Pitt made the film adaptation into an action/horror hybrid, but at least made it fun by giving us a hero worth rooting for.

Retired United Nations investigator Gerry Lane (Brad Pitt) is forced to leave his wife and children behind (in safety, nonetheless) to travel the world in search of a cure to the pandemic turning people into mindless, angry, cannibalistic monsters. What makes Pitt’s World War Z protagonist a badass is the lengths he will go to save the world, even if that means giving his own life.

Brad Pitt in Ocean's Eleven

9. Rusty Ryan (Ocean’s Eleven)

It may have been Danny Ocean’s show, but Rusty Ryan was the showrunner. The secret to how Steven Soderbergh’s 2001 remake of Ocean’s Eleven-- about a parolee (George Clooney) who recruits 10 other professional criminals to nab the ultimate Las Vegas jackpot by robbing three casinos in one night -- became one of the coolest movies of its, or really any, generation is, arguably, Brad Pitt.

From his impeccably calm line delivery, aspirational sense of style, and the unusual aura of sophistication he brings to snacking on a carton of nachos, Brad Pitt made his character the ultimate badass of Ocean’s Eleven. The criminal lifestyle is the one that comes with a price, but Rusty Ryan makes it look priceless.

Brad Pitt in Legends of the Fall

8. Tristan Ludlow (Legends of the Fall)

There are several key moments throughout the 1990s which could be credited as the beginning of Brad Pitt's reputation as a Hollywood hunk and several that could mark the beginning of his reputation as a badass. I feel that a good candidate for both might be the 1994 World War I-era drama Legends of the Fall.

Brad Pitt gives a Golden Globe nominated performance as Tristan Ludlow, one of three brothers living in the Montana wilderness with their father (Anthony Hopkins), whose relationship is tested when he and his brother Alfred (Aidan Quinn) fall in love with Susannah (Julia Ormond), the fiancée of their younger brother, Samuel (Henry Thomas), after he is killed in the war. Of course, Susannah cannot help but choose Tristan, the charming war hero and globe-trotting man of the wild. You could also say he is the kind of man who would willfully go toe-to-toe with a bear.

Brad Pitt in Troy

7. Achilles (Troy)

In 1250 B.C., Trojan prince Paris (Orlando Bloom) convinces Spartan Queen, Helen (Diane Kruger), to leave her husband (Brendan Gleeson) for him, igniting a war. Keeping Troy’s undefeated reputation in mind, the Greeks enlist the help of the greatest warrior known to man: Achilles (Brad Pitt)

If there is just one reason to watch director Wolfgang Peterson’s 163-minute 2004 adaptation of Homer’s poem “The Iliad,” it is Brad Pitt’s performance as the resilient, unmatched, legendary Achilles, tearing through his enemies like a knife through hot butter with no sense of mercy. Even if Troy turned out to be a critical misfire with underwhelming box office returns and Pitt himself credits it as a huge turning point in how he chooses projects, at least he can credit his role as an undisputed badass.

Braad Pitt and Morgan Freeman in Se7en

6. David Mills (Se7en)

In a world defined by unrelenting grimness, where corruption is its spirit and humanity is its prey, Lt. William Stone (Morgan Freeman) is desperate for an escape. Meanwhile, newly minted hotshot detective David Mills (Brad Pitt), his partner on a case tracking down a killer inspired by the Seven Deadly sins, is ready to grab this miserable existence by the balls and bring it to its knees, if only he knew what fate awaits him.

Until its devastating conclusion, Brad Pitt’s David Mills spends most of David Fincher’s grisly 1995 noir masterpiece Se7en exhibiting a nearly indulgent outlook to his otherwise dismal job, unfazed by his partner’s dispirited nature and assuming himself to be an incorruptible force against evil. It is an admirable and decidedly badass quality to attain, despite proving to have no avail in the film’s unnamed setting: a place that evil calls home.

Brad Pitt in Snatch

5. Mickey O’Neil (Snatch)

Brad Pitt’s undeniably badass role in Guy Ritchie’s classic sophomore directorial outing is purely a testament to the actor’s physicality. This is not only due to Irish Gypsy Mickey O’Neil intense fighting ability, but because there is not a single line of decipherable dialogue spoken by the character throughout the film.

Brad Pitt was actually so impressed by Guy Ritchie’s 1998 debut Lock, Stock and Two Smoking Barrels that he personally asked the filmmaker to be in whatever he would do next, inspiring him to rewrite Snatch with a role specially created for the actor. This explains why the often misunderstood boxer’s role feels so loose from the diamond hunt at the center of the plot, yet Mickey O’Neil still ended up becoming, arguably, the film’s most memorable (and undeniably badass) character.

Brad Pitt in Fury

4. Sergeant Don “Wardaddy” Collier (Fury)

I guess Brad Pitt just has the look of a 1940s military officer because Fury, from director David Ayer, is one of two World War II-era films mentioned on this list, but he has starred in a handful. His role as a gruff tank commander fixing to toughen up his young new gunner (Logan Lerman) is one of his darker and, of course, badass characters in that regard.

The quality of his fatherly leadership and resilience in the face of the enemy makes Sergeant Don “Wardaddy” Collier an army of his own. His decision to stay and face a fleet of German soldiers even with his titular tank is an act of valor few people would be willing to make.

Brad Pitt in Once Upon a Time... In Hollywood

3. Cliff Booth (Once Upon A Time… In Hollywood)

Leonardo DiCaprio played the role of film and TV star Rick Dalton in Once Upon a Time In Hollywood. However, I walked out of Quentin Tarnatino’s love letter to the industry’s Golden Age feeling that I would much rather be his second banana, Cliff Booth.

Brad Pitt won an Oscar for making an overly confident, down-on-his-luck stuntman who may or may not have murdered his wife, somehow, the most likable gent in a movie that fuses a fictionalized behind the scenes look at celebrity in the 1960s with revisionist history lesson in the Manson Family. Even during his hilarious quarrel with Mike Moh’s Bruce Lee to his intense visit to Spahn Ranch to his bloody, acid-laced final stand-off nearly the film’s conclusion, Cliff Booth never ceases to emit the kind of charming magnetism you would have to kill for (which, in his case, is not unlikely).

Brad Pitt in Inglourious Basterds

2. Lt. Aldo Raine (Inglourious Basterds)

Despite the fact that Brad Pitt has top billing, the real hero of Inglourious Basterds is not his character, Lt. Aldo Raine, but Melanie Laurent’s French-Jewish cinema operator Shoshanna. However, every minute of screen time featuring the leader of the special unit of Nazi scalpers is owned by Pitt.

The hick-accented, neck-scarred soldier’s commitment to bringing the greatest villains of World War II to justice, made especially evident by the eloquent savagery of his introductory speech to his Jewish-American brethren, makes him as fearsome as it does admirable. Lt. Aldo Raine may have his moments of bumbling (essentially giving up any effort for a convincing Italian accent at a movie premiere crawling with Nazis), Brad Pitt’s first collaboration with writer and director Quentin Tarantino was a match made in history rewriting heaven.

Brad Pitt in Fight Club

1. Tyler Durden (Fight Club)

Many would agree that Tyler Durden is the ultimate Brad Pitt role, if not one of the top 10 ultimate movie characters in cinematic history. As the unlikely companion to Edward Norton’s anxious nobody in the formation of the titular Fight Club, he redefines what men aspire to be, for better or worse.

It is difficult not to get lost in, and almost be inspired by, the clearly heinous and despicable philosophies preached by Tyler Durden in this 1999 adaptation of Chuck Palhniuk’s novel that satirizes modern consumerism’s influence on toxic masculinity, but how can you resist the words coming from a guy who looks like you want look and is free in all the ways that you are not? Fight Club is yet another collaboration between Brad Pitt and David Fincher that sees the world through a deeply cynical and antagonistic lens, which the unforgettable portrayal of Tyler Durden makes an irresistible classic.

Needless to say, Brad Pitt is, and has always been, a badass. But, he is even more than that: he is an Oscar-winning badass.