The 15 Funniest Brad Pitt Performances


By Old Hollywood standards, leading men were generally expected to play the same personality type in all of their films for trust-establishing, audience-appeasing reasons. Today, performers are welcomed to transform for roles on a much more frequent basis.

While he has technically not gone full method, like some of his contemporaries, Brad Pitt still draws massive turnouts, regardless of whether or not he is relying on his dramatic chops or comedic sensibilities. The following 10 are cinematic examples of him in peak form, whilst living in the latter.

Updated on August 1st, 2022 by Colin McCormick: Brad Pitt’s new movie Bullet Train looks to be a wild action movie but it is also clear that it is yet another movie that will show Pitt’s comedic side. As much as the Oscar-winning actor can deliver an intense dramatic performance, he has shown many times that he can also be hilarious. In fact, there are even more funny Pitt roles that fans can take a look at to get some laughs from the Hollywood superstar.


The Lost City (2022)

Brad Pitt in The Lost City
  • Available on Paramount+, Epix and DIRECTV

It seems to be that some of Pitt’s funniest roles are all-too-brief. The recent adventure movie The Lost City was a perfect example of this. Sandra Bullock stars as an adventure novelist who is kidnapped while her book cover model (Channing Tatum) comes to rescue her.

RELATED: Brad Pitt’s 10 Most Iconic Movie Quotes

However, the real rescuer is Pitt, a highly trained operative who is immensely impressive to everyone. There are a lot of funny jokes about Pitt’s good looks and him chastising Tatum for punching bad guys who he already knocked out. It is a shame that he exits the movie so abruptly.

Deadpool 2 (2018)

Deadpool 2 Brad Pitt cameo Vanisher
  • Available on Disney+, FX Now and DIRECTV

While Deadpool 2 could technically mark Pitt’s first live-action superhero movie, it is almost too small of a part to really count. Deadpool assembles a team of powerful mutants known as X-Force, including the invisible mutant Vanisher.

It makes for a funny running joke as it is never clear if Vanisher is really there since he is invisible. Unfortunately, Vanisher is there when he gets electrocuted by a power line, and it is briefly revealed that it was Pitt the whole time. It is a quick surprise that provides one of the biggest laughs in the movie.

War Machine (2017)

It seems every time Pitt plays a military leader, it is inevitably a character who is not the brightest person around. Such is the case in the overlooked Netflix comedy War Machine. Pitt stars as General Glen McMahon, an experienced military man who finds himself in charge of a war no one thinks can possibly be won.

Pitt really commits to his hardened and gruff performance which is hilarious the more lost and disillusioned the general gets. While the movie itself is largely forgotten, Pitt does deliver some solid laughs.

Friends (1994-2004)

Pitt stepped into the sitcom world as one of the funniest guest stars on Friends. Pitt appeared in the episode “The One with the Rumor” as Will, a former classmate of Ross’ who joins the group for Thanksgiving dinner. In a bit of meta-casting, Will also has a deep hatred for Rachel, played by Pitt’s then-wife Jennifer Anniston.

As fun as that gimmick is, Pitt is genuinely funny, playing off the show’s beloved characters and portraying someone who was not popular or good-looking in high school.

Mr. & Mrs. Smith (2005)

Brad Pitt Mr and Mrs Smith
  • Available to rent on Apple TV

The action movie Mr. & Mrs. Smith is probably best known for uniting Pitt with Angelina Jolie and the media storm that resulted from that. However, there is a lot to enjoy about the movie on its own, including its sharp sense of humor.

RELATED: Brad Pitt’s 15 Best Movies, According To Letterboxd

Pitt is particularly funny in his role, playing off the super-spy aspects of the character along with the domestic squabbles of the central relationship. He makes for a cool action hero but isn’t afraid to look a little goofy as well.

Killing Them Softly (2012)

  • Available on Starz and DIRECTV

There are black comedies. And then there is Killing Them Softly. Andrew Dominik’s initially misunderstood, but now more appreciated heist ensemble sees Brad Pitt take on a role he very rarely plays. While he is not necessarily the villain, he surely is in the business of killing for hire, as Jackie Cogan.

Relentless in his pursuit of getting paid, in spite of his employers keeping him ever on the runaround, the film culminates in a few brutally honest, sardonic quips delivered by Pitt that evoke the larger flaws of capitalism in America. Consequently, the film is one that will stick with most viewers long after the credits roll.

Megamind (2010)

  • Available on Prime Video

Before his brief role in Deadpool 2, Pitt had the chance to play an animated superhero in the comedy Megamind. In the largely-forgotten and vastly underrated requiem for a supervillain character study, the titular Megamind (Will Ferrell) is lost without a purpose after finally defeating his good-guy nemesis (Pitt).

Pitt does a great job of playing the arrogant and pompous hero figure that plays on the likes of Superman. There is also a twist with the character that makes him even funnier.

Moneyball (2011)

  • Available on Fubo TV, Hulu, AMC+, Roku and DIRECTV

Pitt garnered an Oscar nomination for his turn in Moneyball, the sports movie based on a true story. Pitt plays Billy Beane, the manager of the Oakland Athletics who takes a new approach to winning at baseball using mathematics. While Billy is a grounded character, Pitt brings a lot of charm and humor to the role.

Not surprisingly, his new method doesn’t sit well with everyone and many of the funniest scenes in the movie involve Billy frustratingly trying to express his vision to those he works with. There is also some funny chemistry between Pitt and co-star Jonah Hill.

Ocean’s Eleven (2001)

  • Available on HBO Max and Peacock Premium

“Rusty” Ryan is one of the key members of the movie heist squad in Steven Soderbergh’s Ocean’s Eleven, Ocean’s Twelve, and Ocean’s Thirteen Brad Pitt is not without charm, nor his knack for endless punchlines.

However, underrated moments of humor also derive from his continuous ability to surprise his fellow heist-men with the scientific and technological knowledge he casually drops. Though to be fair, Rusty would not be the two-man in Danny’s 11-turned-12-turned-13-member team if his intelligence quotient was not up to snuff.

Inglourious Basterds (2009)

  • Available on TNT, TBS and DIRECTV

One viewing of Pitt trying to pass off as Italian at a doomed movie premiere and Aldo Raine in Inglourious Basterds cements himself as one of Quentin Tarantino’s funniest characters from any of his movies. Aldo is the leader of the titular team of Jewish soldiers who proves he is an effective warrior and terrible spy.

Though the film’s ensemble-first credo would ultimately reduce Pitt’s screen time just out of serious contention to earn any awards consideration, his top billing is not without merit, as all roads in the film lead back to Pitt’s Lt. Aldo Raine, and the German will fear him.

True Romance (1993)

  • Available to rent on Apple TV

A literal moment before he would become a household name for good, Pitt took on the role he was born to play: the stoner, couch potato roommate in a Quentin Tarantino-penned movie.

RELATED: 11 Best Directors Brad Pitt Worked With

Of course, it would be nearly two decades before Pitt would be directed by Tarantino himself. But in 1993, he worked wonders as Floyd – the giggle-prone, perma-stoned squatter whose zen way of being makes him the right man for any and all high-tension situations – just as another Pitt/Tarantino character would come to be, some 26 years later.

Twelve Monkeys (1995)

In fictional media that commendably places a mirror to real-life events in too-fully-baked-to-be-faked ways, there is often a standout, misunderstood, silenced, or even institutionalized character spewing all the answers and then some.

Twelve Monkeys was not Pitt’s last outing playing a gifted mind with a strong feel for life in post-viral pandemic circumstances, as World War Z and his turn on Saturday Night Live as Dr. Anthony Fauci were just two decades away. Terry Gilliam’s time travel-heavy narrative did represent a pivotal moment in his then-jettisoning career, though. He earned his first Oscar nomination as the high energy show-stealer, Jeffrey Goines.

Fight Club (1999)

  • Available to rent on Apple TV

The dark satire Fight Club has Pitt is perhaps his most iconic role as Tyler Durden. As an anarchist and dangerous influence, Tyler is the kind of character who should be unlikeable but audiences can’t help loving. A big part of that is from his bizarre and twisted sense of humor.

Tyler messes with society in small and disturbing ways in his jobs as a waiter and projectionist. And his general worldview is a balance between thought-provoking, unsettling, and downright hilarious ideas.

Once Upon A Time … In Hollywood (2019)

  • Available on Fubo TV and DIRECTV

Fresh in everyone’s minds as the acid cigarette-tripping savior of Tarantino’s latest effort, Brad Pitt’s Cliff Booth – a role for which he won his first acting Oscar – operates to the beat of a different drum.

Needless to say, if every anxious and insecure actor had a stunt driver/right-hand man always at their beck and call with unconditional jokes and smokes, there would be less tension throughout the town made of dreams, as evidenced by the revisionist finales to end all revisionist finales, where a real-life nightmare became anything but.

Burn After Reading (2008)

A triumph for the Coen Brothers in this eclectically on-brand Best Picture followup was somehow managing to dial back on Pitt’s sex appeal.

In a film that co-starred his frequent collaborator and fellow tabloid cover-hogger, George Clooney, the crew’s challenge of characterizing Pitt as an in-over-his-head, hyperactive moron with more screws loose than one proved daunting enough to plunge into with all of their cards. A few iconic GIFs later, and even Burn After Reading staunchest detractors can agree that Pitt made off with everyone’s hand (while he never stopped fist-pumping, even after the closet scene).

NEXT: Brad Pitt’s 10 Lesser Known Movies You Might Not Have Seen

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