Moviegoers have flocked to the theaters recently to see the new action-adventure film The Lost City. The movie stars Sandra Bullock and Channing Tatum as unlikely adventurers, as well as Daniel Radcliffe in an antagonist role. Most notably, the trailers also promote the appearance of high-profile blockbuster actor Brad Pitt.
Brad Pitt is Hollywood royalty at this point, having made many appearances in comedy films and TV shows. Sometimes, he nets a starring role, while other times he plays a supporting actor to the film's other stars. These performances throughout Brad Pitt's career find the actor at his funniest, even when it's not his most well-known.
10 J.D. – Thelma & Louise
One of Brad Pitt's first major roles in a film was Ridley Scott's Thelma & Louise. Released in 1991, Pitt takes on a supporting role to the film's stars, Susan Sarandon and Geena Davis. The actor plays J.D, a young man who the titular characters encounter during their run from the police and shares many similarities with them.
As a drifter, J.D. comes off as very appealing to Davis's Thelma, and the two sleep together. However, the next morning, J.D. is gone, having taken Thelma's life savings. This brief appearance was enough to kickstart Brad Pitt's burgeoning movie career, all the while getting to be charming and witty enough to woo Geena Davis.
9 Will – Friends
In 2001, Brad Pitt was married to Jennifer Aniston, who at the time starred as Rachel Greene in the hit NBC sitcom Friends. In the show's eighth season, Pitt made a guest appearance on his then-wife's show as Will Colbert. Will is a friend of Ross who went to high school with most of the gang, though he still harbors grudges against Rachel.
After reuniting at Thanksgiving dinner, Will reveals that he and Ross formed the "I Hate Rachel Greene Club" in high school. Will was angry about Rachel's attitude towards him back then, while Ross feels awkward bringing up his old feelings towards her. The audience just can't get enough of this couple playing sworn enemies.
8 The Mr. – Mr. & Mrs. Smith
Brad Pitt would co-star alongside Angelina Jolie in 2005's Mr. & Mrs. Smith. The couple plays a husband and wife who discover that they are both secret assassins. To make matters even more complicated, they have both been assigned to kill each other, leading to an action-packed confrontation.
While these roles are also great opportunities for Jolie and Pitt to flex their action movie chops, they also elevate the movie with their charismatic performances. Their chemistry was also enough to spark the actors' real-life romance. Though after watching Pitt's performance in this movie, who could blame her?
7 Chad – Burn After Reading
Pitt would later make his Coen Brothers film debut in 2008's Burn After Reading. This is perhaps one of Pitt's funniest performances, as he plays a clueless gym employee named Chad. In the film, he teams up with his co-worker Linda (played by Frances McDormand) to blackmail a government official (played by John Malkovich).
Chad's characterization here by Pitt is nothing short of comedic perfection. This is most prevalent in a scene where Chad calls Malkovich's Osbourne Cox offering the return of "classified documents" in exchange for money. Any fan of Pitt's work should put this movie on their watchlist, as they will not be disappointed by his hilarity.
6 Metro Man – Megamind
Voice-acting in animation is an easy way for successful actors like Brad Pitt to reach a younger audience. Pitt does this masterfully in Megamind, a DreamWorks animated film starring Will Ferrell and Tina Fey. Here, Pitt voices Metro Man, a Superman-esque figure who constantly battles his titular arch-nemesis.
However, the film's plot is truly kick-started by Megamind's unexpected defeat of Metro Man. Pitt's superheroism is sadly cut short, but -- spoiler alert! -- that's not the last audiences see of this character. As it turns out, Metro Man faked his death in order to retire from crime-fighting, awkwardly encountering Megamind later in the film.
5 Ben Rickert – The Big Short
Adam McKay's The Big Short features an all-star cast, from Steve Carrell and Ryan Gosling to cameo appearances by Selena Gomez and Margot Robbie. The film follows several stories of financial experts who accurately predict and take advantage of the 2007 housing market crash. Brad Pitt has a brief appearance as Ben Rickert.
Recruited by partners at Brownfield Fund, an investment firm, Ben aids them in shorting their mortgage securities. The film does a deep dive into all the financial world and housing market lingo, so those curious should watch the film to see how Ben plays into all this. Pitt gives a memorable performance as a stoic stock trader.
4 A Brief Stint As Comedy Central Weatherman
One of Brad Pitt's most unexpected roles is on Comedy Central's late-night political talk show, The Jim Jefferies Show. Hosted by Australian-American comedian Jim Jefferies, the show is akin to other comedic news satires like The Daily Show and Last Week Tonight. However, Jefferies had an edge by recruiting Pitt for the first season.
Pitt, a fan of Jefferies' comedy, joined the show's first episode as a weatherman talking about climate change. Future episodes would see Pitt's character return before being fired by Jefferies, then re-hired after fan demand. While the show didn't receive a lot of attention, Pitt's guest appearances were frequently a highlight for fans.
3 Glen McMahon – War Machine
Brad Pitt has been a staple in plenty of war films, from World War Z, to Troy, to Fury. However, Pitt got to take the genre a little less seriously with 2017's war satire, War Machine. Though the film's title has no relation to Don Cheadle's Marvel character, it finds Pitt slipping into comedy with charming ease.
Playing General Glen McMahon, the film parodies the reality of war, looking at the mundaneness rather than the battles. Pitt stars alongside a stellar cast of comedic and dramatic actors, including Topher Grace, Lakeith Stanfield, and even Ben Kingsley. The film didn't get great reviews, but the cast and comedy were all praised by critics.
2 Cliff Booth – Once Upon A Time In Hollywood
Pitt made his debut in a Quentin Tarantino-directed film with Inglorious Basterds. However, his second shot in front of Quentin's camera might be one of the funniest performances of his career. In Once Upon A Time In Hollywood, Pitt plays Cliff Booth, the out-of-work stuntman to Leonardo DiCaprio's fading movie star, Rick Dalton.
This role finds Pitt perfectly cast as Dalton's laid-back, slightly unhinged best friend. He gets to spar with Bruce Lee, flirt with Manson girls, and, of course, take his shirt off. However, Pitt's highlights in the movie come from the third act, where he gets involved in a drug-fueled confrontation with Manson members at Dalton's estate.
1 A COVID-Safe Appearance – Saturday Night Live
When COVID-19 first hit the United States, forcing a national lockdown, it seemed like a dark moment for the entertainment industry. However, the show must go on, and Saturday Night Live returned in April 2020, comprised of sketches filmed by the cast at home. More episodes would follow in the ensuing months of quarantine.
Brad Pitt appeared in the second episode, which aired on April 25, 2020. Appearing in the cold open, Pitt fulfills the wishes of White House Coronavirus Task Force member Dr. Anthony Fauci by portraying him on the show. While Pitt's appearance is brief, it's a lovely tribute to Fauci and a reminder of Pitt's comedic strengths, even in lockdown.