Top 15 Brad Pitt Funniest Portrayals

Brad Pitt is a Hollywood superstar and an epitome of a successful actor. He is handsome and very talented. He brings the charm to any role he plays that makes the viewers swoon. On top of that, he is such a diverse actor that can nail any type of character.
Many fans love Brad Pitt for his comedy roles. He brings a year of joy to audiences with his funny starring in several movies such as Friends, Dread Pool 2, Moneyball, and the list goes on. Whether it’s a lead character or supporting role, he leaves massive impressive and so much fun for viewers.In this post, we highlight the top 15 Brad Pitt performances that make us actually chuckle. Check them out and share with us your own opinion.

#15 Mr. & Mrs. Smith (2005)

Mr. & Mrs. Smith is such a successful hit in 2005. It attracts audiences thanks to the incredible chemistry of the 2 main actors – Brad Pitt and Angela Jolie. That also led to the marriage of these 2 talented stars thereafter.
On top of that, the performance of Brad Pitt in this action movie is so remarkable. He successfully delivered his character – a cool, yet a bit goofy superhero. That gives audiences so much fun and makes them love this character more.

#14 Moneyball (2011)

Moneyball gave Pitt an Oscar nomination. In the movie, Pitt portrayed Billy Beane, the manager of Oakland Athletics who applies new avenues to winning at baseball using mathematics. Although this is a grounded character, Pitt jazzed up his role by adding some fun vibes.
Of course, these new avenues aren’t compatible with many people. That engendered many hilarious scenes, including the moment when Billy frustratingly tried to express his vision to those he works with. Besides, the funny chemistry between Pitt and co-star Jonah Hill makes the movie worth it.

#13 Inglourious Basterds (2009)

One look at Pitt pretending to be Italian at a fatal movie premiere, and Aldo Raine in Inglourious Basterds cements himself as one of Quentin Tarantino's funniest characters in any of his films. Aldo leads the titular unit of Jewish soldiers and demonstrates that he is both an effective fighter and a poor spy.
Though the film's ensemble-first philosophy would eventually restrict Pitt's screen time just enough to keep him from being considered for any Oscars, his top billing is not without significance, as all roads in the picture lead back to Pitt's Lt. Aldo Raine, and the German will fear him.

#12 Killing Them Softly (2012)

There is some dark comedy. There's also Killing Them Softly. Brad Pitt takes on a character he rarely plays. Andrew Dominik's initially misunderstood, but now highly appreciated heist ensemble. While he is not necessarily the villain, as Jackie Cogan points out, he is in the business of killing for pay.
Despite his employers' efforts to keep him on the run, Pitt is relentless in his pursuit of payment, and the film concludes with a few brutally honest, sardonic comments delivered by Pitt that recall the wider problems of capitalism in America. As a result, most audiences will remember the film long after the credits have rolled.

#11Ocean's Eleven (2001)

"Rusty" Ryan is a prominent part of Steven Soderbergh's Ocean's Eleven, Ocean's Twelve, and Ocean's Thirteen heist crew. Brad Pitt is not without charisma, nor does he lack the ability to come up with countless punchlines.
However, underrated moments of levity stem from his ongoing capacity to astound his fellow heist-men with the scientific and technological expertise he casually drops. To be honest, Rusty would not be the two-man in Danny's 11-turned-12-turned-13-member team if his intelligence was not up to par.

#10 War Machine (2017)

Unlike the war film, he played before, Pitt took his role in War Machine less a little less seriously. Even though the title has nothing to do with Don Cheadle's Marvel character, Pitt slips into comedy with wonderful ease.
Pitt fully commits to his tough and gruff act, which becomes increasingly humorous as the general becomes increasingly lost and disillusioned. While the film itself is virtually forgotten, Pitt provides some good laughs.

#9 True Romance (1993)

Pitt took on the role that he was born to play: the stoner, couch potato roommate in a Quentin Tarantino-penned film, literally moments before he became a household celebrity for good.
Of course, it would be over two decades before Tarantino directed Pitt himself. But, 26 years later, he did wonders as Floyd, the giggle-prone, perma-stoned squatter whose zen way of making him the appropriate man for any high-tension situations.

#8 Burn After Reading (2008)

Pitt made his Coen Brothers cinematic debut in 2008 with Burn After Reading. He plays a naïve gym staffer named Chad in the movie and makes audiences laugh out loud with his funny moments.
Pitt's portrayal of Chad here is nothing short of hilarious. This is particularly evident in a scene in which Chad phones Malkovich's Osbourne Cox and offers him money in exchange for the return of "secret documents." Any Pitt fan should put this film on their watch list because they will not be disappointed by his humor.

#7 Twelve Monkeys (1995)

Twelve Monkeys was not Pitt's final performance as a brilliant mind with a keen sense of life in post-viral pandemic circumstances because World War Z and his appearance as Dr. Anthony Fauci on Saturday Night Live were just two decades away. The time travel-heavy story by Terry Gilliam did, however, mark a turning point in his then-dying career. He received his first Oscar nomination for his performance as Jeffrey Goines, a high-energy show-stealer.

#6 Megamind (2010)

In the comedy Megamind, Pitt had the opportunity to portray an animated superhero. After eventually beating his good-guy rival, the titular Megamind (Will Ferrell) is lost without a goal in the mostly forgotten and remarkably underestimated requiem for a supervillain character study (Pitt).
Pitt does a fantastic job portraying the haughty and conceited hero persona that mimics Superman. The character has a twist as well, which makes him much more amusing.

#5 Once Upon A Time ... In Hollywood (2019)

Brad Pitt actor

With Inglorious Basterds, Pitt made his feature film debut under Quentin Tarantino's direction. But he may have had one of the funniest performances of his career during his second appearance in front of Quentin's camera. In the film Once Upon A Time In Hollywood, Pitt plays Cliff Booth, the unemployed stuntman to Leonardo DiCaprio's waning movie star.
Pitt is a fantastic fit for the role of Dalton's laid-back, slightly insane best friend in this movie. He has the opportunity to spar with Bruce Lee, flirt with Manson girls, and of course, strip off. Pitt, though, really shines in the third act when he gets into a drug-fueled altercation with Manson members at Dalton's mansion.

#4 Fight Club (1999)

Brad Pitt performance

Tyler Durden in Fight Club is one of the most iconic roles of Brad Pitt. Tyler is the kind of dangerous anarchist character that viewers ought to find repugnant but end up loving. That comes in large part from his peculiar and perverted sense of humor.

#3 Friends (1994-2004)

Brad Pitt movies

Friends is a sitcom series that requires no introduction. Pitt played Will, Ross' former classmate who joins the group for Thanksgiving dinner, in the episode "The One with the Rumor." Will also harbors a strong dislike for Rachel, who is portrayed by Pitt's ex-wife Jennifer Anniston, in a clever use of meta-casting.
Pitt is truly humorous, riffing off the show's favorite characters and assuming the role of someone who wasn't popular or attractive in high school. Just as fun as that gimmick is.

#2 The Lost City (2022)

Brad Pitt

Pit t tends to play comic characters that are all too fleeting. The Lost City, a recent adventure film, served as the ideal illustration of this. Channing Tatum plays the book cover model who arrives to save Sandra Bullock's character, an author of adventure novels who gets abducted.
Be that as it may, the real rescuer is Pitt, who is incredibly impressive to everyone. Many humorous jokes make light of Pitt's excellent looks and his reprimanding of Tatum for striking out at bad guys he had already knocked out. Unfortunately, he leaves the movie so quickly.

#1 Deadpool 2 (2018)

Brad Pitt

Pitt's role in Deadpool 2 may theoretically be considered his debut in a live-action superhero film, but it is nearly too minor to matter. Deadpool assembles the X-Force, a group of strong mutants that includes the invisibility mutant Vanisher.
Since Vanisher is invisible, it's never certain if he's present, which provides for an amusing running joke. Pitt is momentarily revealed to have been the victim the entire time, but sadly Vanisher is present as he is struck by a power line and dies. One of the movie's biggest chuckles comes from a sudden surprise.
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