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20 Things About Brad Pitt's Career That Make No Sense

Like many huge Hollywood stars, Brad Pitt has effectively lived two lives: his real life and the tenuous thread created by all of his on-screen characters. And just like Al Pacino explains in Once Upon a Time in Hollywood, most audiences see that through-line more than they see the real person. In short, people think of Brad Pitt as the sum of his performances.

But no matter how big a movie star he may be, Pitt definitely took on some roles that might not have been 100% in line with his personality and values—it's just part of building a long, steady career. Later in life, though, as he's been able to become more choosy in what movies he does or doesn't take on, perhaps the real Brad Pitt is shining through the cracks.

But the few clues that fans have picked up on about Brad Pitt's inner life only serve to spawn more questions about the man. Keep scrolling for 20 things about Brad Pitt's career that make no sense.

20 The Mail Room Clerk

via Us Weekly

Anyone who looks at a photo of a young Brad Pitt can tell the future holds bright things. The official record skips over how exactly Pitt got discovered, but Hollywood lore holds that he slipped his own headshots into stacks for casting while working in a mailroom. But the story just doesn't check out given his show-stopping good looks.

19 Thelma & Louise

via IMDb

Pitt's first big movie gig came in the 1991 Ridley Scott film Thelma & Louise. He took things past the typical cowboy vibe of a white t-shirt and jeans when he popped that t-shirt off and revealed the body that would propel him to superstardom. But as much as everyone remembers those abs, his acting in the film actually caught many eyes in Hollywood, as well.

18 True Romance

via Pinterest

After Thelma & Louise, Brad Pitt starred in the 1992 Robert Redford-directed flyfishing and family saga A River Runs Through It. His moody performance earned even more attention, though it would be in 1993 that he'd pick up a small gig in True Romance that would make him an underground star. But was his lazed-out hippy Floyd the true Brad Pitt revealed?

17 What's in the Box?

via tvovermind

Probably one of the most famous Brad Pitt lines—and one that everyone loves to quote endlessly—came at the end of the David Fincher noir thriller Seven, when his character begs, pleads, and screams, "What's in the box?" Everyone should know what was in the box by now, but it's the peculiarity of Pitt's delivery that makes the line so memorable—was it acting genius, though, or just plain luck?

16 GP

via People

After starring in Seven with Gwyneth Paltrow as his on-screen wife, the two young starlets were frequently seen out together and ended up engaged. They broke the relationship off in 1997, though Elle reports that Paltrow remembers how Brad Pitt once confronted Harvey Weinstein about making "a pass" at Paltrow. And yet, Pitt's career didn't get tossed in the trash, like so many others.

15 Interview With A Vampire

via Pinterest

Interview With A Vampire is a movie that transcends its campy appearance and becomes a historical, emotionally laden saga of vampires experiencing the ravages of time. Still, an image of Brad Pitt or Tom Cruise as the fabulously over-the-top vampires brings many questions to mind about the undertones of the films—especially given Kirsten Dunst's frozen-in-time, young character.

14 Jen & Friends

via E! News

One of the most hilarious moments in Brad Pitt's career came when he received an Emmy nomination for Outstanding Guest Actor in a Comedy Series. He had shown up in an episode of Friends, which probably came as no surprise since he was married to Jennifer Aniston at the time. But let's be honest, the tabloid juiciness earned him that nom, not a performance on Friends.

13 Self Improvement

via Vice

One of Brad Pitt's biggest and most iconic roles was when he played Tyler Durden in 1999's Fight Club. Not only was the grungy pic a mind-twisting rendition of the Chuck Palahniuk novel, but it also marked Pitt's second film being directed by David Fincher. Pitt was all abs and biceps for the movie, which made his line about self-improvement seem all the more self-referentially ironic. And yet somehow, he made it work.

12 Do Ya Like Dags?

via whatsontv

One of the more notorious roles that Brad Pitt has ever taken on was when he played a pikey in Guy Ritchie's Snatch. The bare-knuckle brawler is borderline incomprehensible, though his fists do the talking just as well as his staccato lines, like "Do ya like dags?" But the real hilarity comes with the knowledge that Brad Pitt loved Lock, Stock and Two Smoking Barrels so much he asked Ritchie for a role in his next film, only to be unable to master the proper accent—so Ritchie made him the caravan-loving gypsy.

11 Achilles And His Cousin

via Pinterest

When Warner Bros starting casting for the epic swords-and-sandals film Troy (written, coincidentally, by future Game of Thrones co-creator David Benioff), was there anyone who could have played Achilles other than Brad Pitt? The answer is a no, even if the movie itself barely manages to suspend disbelief. Still, Pitt's turn in the movie, alongside his cousin (as played by a young Garrett Hedlund) was really, truly not too good. Or was it?

10 Mr. Smith, Please

via IMDb

Most movie stars, male and female and otherwise, want to keep playing younger roles for as long as they possibly can. After all, once the looks go, the career typically goes, too. But one of the more confusing career moves for Brad Pitt came when he joined up with Angelina Jolie to play dueling spies in Mr. & Mrs. Smith. But they played the roles perfectly!

9 Angelina, Is That You?

via playpilot

In fact, Brad Pitt and Angelina Jolie played their roles to such perfection in Mr. & Mrs. Smith that it seems they wanted to keep on doing so forever. Not long after the movie's 2005 release, Pitt and Jolie were a couple, then married, then with children, then squabbling, presumably some therapy in the mix (just like in the movie) and now separated.

8 Those Ocean's Movies

via Looper

Ensemble films can be a bit of a tricky act to pull off on the screen—so just imagine how the producers feel trying to massage every tender ego on the set of one of these blockbusters. But as gnarly as all the emotions must get, some ensembles get back together again and again, like Brad Pitt et al in the modern Ocean's films. But why didn't Brad Pitt ever take over the films more?

7 The Tree of Life

via Collider

Very little about Terrence Malick's 2011 voice-over narrative The Tree of Life makes sense—and it's not supposed to, probably. But Brad Pitt's role in the movie left a lot of people wondering about the actor's childhood. Based on his longstanding career, in which he plays many surprisingly vulnerable men, the emotional viciousness of this role seemed to be inspired by something dark.

6 12 Years A Slave

via Hollywood

After Mr. & Mrs. Smith, Pitt started taking on producer duties on most of the films he's appeared in. But the question always remains whether he got the gig for his acting first, then decided to produce, or vice versa. In the case of 12 Years a Slave, it definitely seems like the latter is the likely explanation given his semi-forced performance in a pretty middling role.

5 A Passion for Architecture

via The Telegraph

When you're Brad Pitt, you can do pretty much anything you want. In Pitt's case, he discovered a love for architecture and decided to follow his passion, in the case of this image visiting Frank Lloyd Wright's masterpiece, Fallingwater. He also interned for Frank Gehry and designed houses for post-Katrina New Orleans.

4 New Orleans Buildings

via Architectural Digest

While Brad Pitt has definitely excelled in cinema, he's run into a bit of a snag in his architecture career. To be fair, his heart was in the right place when his Make It Right Foundation rebuilt houses that were damaged due to flooding caused by Hurricane Katrina. But now, defects in those houses have led to lawsuits flying ever which way, as reported by Insurance Journal.

3 Lieutenant Aldo Raine

via pophorror

Brad Pitt dove headlong into his role as Lieutenant Aldo Raine in Quentin Tarantino's WWII masterpiece, Inglourious Basterds. The movie follows Pitt's unit as they try to infiltrate German-occupied Paris, with historically hilarious results. But in all reality, was Aldo the Apache's ridiculous accent just an attempt by Pitt to prove he could do accents well?

2 Once Upon A Time In Hollywood

via Vanity Fair

Pitt teamed up with Quentin Tarantino once more for 2019's Once Upon a Time in Hollywood. While everyone went into the film expecting he and costar Leonardo DiCaprio to get some serious macho-man action in, Pitt actually turned out one of the more tender roles of his career. Strange as it seems, his puppy-dog eyes just fit the film perfectly. Whether or not Tarantino expected such a performance is another story.

1 A Leading Man, Sort Of

via YouTube

Pitt's most recent movie, Ad Astra, follows an astronaut as he copes with his daddy issues all the way out in the vicinity of Neptune. Pitt's leading role is, in hindsight, one of the only times he's actually taken on a fully-fledged leading role. Despite his obvious star power and massive Hollywood cache, Pitt hasn't truly been the lead in many of his films, which is surprising, to say the least.

Sources: IMDb, Insurance Journal, and Wikipedia.

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