Only A Real Fan Can Name These Brad Pitt Movies

From the early 1990s onward, actor and producer Brad Pitt gradually rose through the ranks of Hollywood to become one of the most powerful figures in the film industry. Now a leading man in every sense of the expression, like many actors, Pitt initially struggled to find fame and fortune with a handful of minor, uncredited roles, followed by the floodgates bursting open with such force it’s almost unthinkable he would be anything but a top billed actor for every feature in which he appears—unless, of course, it’s just a quick cameo poking at the very nature of his overwhelming fame.

Critics may suggest Pitt’s early success had a lot to do with his looks, yet this is a disservice to his talents as an extremely versatile actor. He’s been at the forefront of blockbusters in the dramatic, comedic, horror, thriller, sports, and war genres, always delivering expert performances no matter the style. Sure, some have made a bit more money than others, but a genuine diehard could probably name the misfires just as easily as they could the classics. In the very least, even if an overall film has a few flaws, Pitt himself almost always gave it his all. Anyone up for that challenge should keep reading for a quiz on Brad Pitt’s filmography that only a true fan could pass.

Question 1

What World War II film featured Brad Pitt as leader of an elite squadron?

Of the many war heroes Brad Pitt has portrayed, none can match the intensity of First Lieutenant Aldo “The Apache” Raine. Leading the most gleefully violent squad the Allied Powers have on their side, Raine’s mission is hunting down the most evil men in history and ensuring the world never forgets their crimes—if he let’s them survive, that is. That’s not to say he was entirely without a sense of humor, as the film features an unforgettable scene where Raine poses as an Italian soldier without dropping his heavy Appalachian accent. Arrivederci.

Question 2

In which historical drama did Brad Pitt play a man opposed to slavery?

Even when the deplorable practice of slavery still existed, there were plenty of people who knew just how terrible it was. Unfortunately, few of them had the power to do anything about it, unlike Brad Pitt’s character Samuel Bass. Hailing from Canada, Bass was a true outsider to the situation, giving him a unique perspective on the treatment Solomon Northup faced throughout this highly acclaimed film. Because of this, he became one of the few people to help Solomon regain his freedom. Pitt also co-produced the film, leading to an Academy Award for Best Picture.

Question 3

What crime drama saw Brad Pitt as a cop partnered with Morgan Freeman?

It should go without saying that taking a human life in cold blood is pretty much the worst sin a person could commit, which is why police officers track down vicious criminals accused of this action with the highest priority. The villain Brad Pitt’s Detective Dave Mills chases in this film is especially vile, using other horrible concepts like gluttony, greed, pride, and envy to make his violent mark on the world. Ironically, it’s Mills himself who fulfills the wrath part in one of cinema’s most shocking twists.

Question 4

In which film did Brad Pitt join a team of con artists?

Brad Pitt may have the name recognition required to bring audiences to the theaters, as did most other actors in this stylish heist film, but a major con is the sort of thing that requires an entire team of criminals to pull off smoothly. Robbing hundreds of millions of dollars from three of the biggest casinos in Las Vegas is definitely that kind of job, so Pitt’s character Rusty Ryan wasn’t going to handle this one on his own. In fact, it wasn’t even his idea, as an old friend who was recently released from prison lead the charge.

Question 5

What movie saw Brad Pitt’s character age backwards?

Looking at the pictures on this quiz, some people might start to wonder if there’s a picture of Brad Pitt hidden in some attic rapidly getting older. While the man himself at times seems ageless, in this film, the exact opposite was true—literally. When his titular character was born, he had the appearance of an elderly man, and at the time of his demise aged 84, he appeared to be a mere baby. Despite this unique condition, Pitt’s youthful personality allows him to find love with an outrageously understanding woman named Daisy.

Question 6

Which female oriented buddy comedy featured Brad Pitt as a hitchhiker?

In many respects, this is where it all began for Brad Pitt’s career. No, it wasn’t his first movie, nor even his first major role, but something significant did happen—he took his shirt off during a key scene, forever endearing himself to the primarily female audience. Even before Pitt’s character, J.D., goes topless, one of the lead characters instantly finds herself smitten with his appearance, allowing the mysterious stranger to rob the other woman of her life savings before disappearing into the night. Amazingly, this theft is still the least of their worries.

Question 7

What film did Brad Pitt appear in as Tyler Durden?

Technically speaking, the first rule of this movie is to never speak about this movie. Not that it really matters, since Brad Pitt’s iconic character Tyler Durden is the one who lays down this law, and in a shocking twist, it could be said the guy doesn’t even really exist. This comes as a huge surprise after two hours worth of what is perhaps Pitt’s most charismatic performance, taking a small group of disenfranchised, violent young men and slowly turning them into a would be terrorist cell called Project Mayhem.

Question 8

In what film does Brad Pitt play a securities trader coaxed out of retirement?

The world of finance is often extremely confusing, even to rising investors who spent their whole lives studying the system. To get their foot in the door, two young men looking for a large payoff call upon Brad Pitt’s Ben Rickert, a retired trader, to help them better understand how to benefit from the market. The downside is that Rickert understands the business well enough to know that it’s going to collapse, quickly becoming worried their actions could contribute to a failing system. Maybe he should’ve just stayed retired.

Question 9

Which movie saw Brad Pitt implement a new system for scouting baseball players?

Who said sports didn’t have anything to do with math? Certainly not the characters in this film, and especially not Brad Pitt’s Billy Beane, General Manager of baseball’s Oakland Athletics during a time when the team, quite frankly, wasn’t doing so well. Knowing some major changes needed to be made for his brand to reclaim their previous glory. Enter an economics whiz named Peter Brand, who has a brand new system called sabermetrics, which the two of them use to hire overlooked and undervalued players with the necessary skills to make the A’s more Athletic.

Question 10

In what war movie does Brad Pitt lead a tank crew?

With a nickname like “Wardaddy,” it’s clear Brad Pitt’s Staff Sergeant Don Collier meant serious business in this World War II blockbuster. Surprisingly, though, the mere fact he commands a unit in control of a state of the art tank doesn’t necessarily mean every mission is a success, and in fact, the first half of this movie sees his crew making a number of serious mistakes, with a rookie newcomer especially causing problems. While they get the act together in the end, the old adage that war is hell proves correct, as there are very few survivors on either side.

Question 11

Which film sees Brad Pitt dealing with the Mexican cartel?

Anyone who has seen their fair share of movies dealing with the cartel knows these crime syndicates are not to be messed with. Brad Pitt’s Westray is certainly aware of this fact, repeatedly telling the lead character of this film he should take great care when attempting to rip them off. After he inevitably ignores this advice, the interloping of a woman named Malkina quickly makes it clear Westray knew what he was talking about, sending both men into a state of panic as they try to escape the consequences of her actions.

Question 12

Which film featured Brad Pitt surviving a zombie apocalypse?

By and large, the average zombie movie starts with the beginning of an outbreak, meaning only a small handful of the undead have risen to terrorize the living. Flipping the script, this apocalyptic film sees Brad Pitt’s former UN advisor Gerry Lane struggling to stop the ongoing onslaught after it’s already well underway. For once ignoring hostile global tensions, pretty much every nation in the world needs to work together to stop the zombies from destroying them all. At this point, it’s not even a matter of victory, as everyone is merely trying to stay alive.

Question 13

What movie saw Brad Pitt and his future wife play married spies?

In the modern era, there are probably a large number of men and women out there who don’t know exactly what it is their husbands and wives are doing for a living. This is especially true of any relationship that isn’t doing so hot, which is definitely the case for Brad Pitt’s John and Angelina Jolie’s Jane as this film begins. Turns out they’re both hitmen, and if that wasn’t shocking enough, they’re next big jobs are, well, each other. In another twist, realizing this fact is ultimately what rekindles their love, although it also infuriates their bosses.

Question 14

In which film does Brad Pitt play a general hired to end the war in Afghanistan?

After playing major roles in a number of films set during World War II, Brad Pitt’s continued interest in the Army shot forward to the present day with this Netflix original. His character, Glen McMahon, has been tasked with ending the highly controversial war in Afghanistan as quickly as possible, a task that was easier said than done, to say the least. It doesn’t help that few world leaders are willing to hear his plans, but the real problem is a young Rolling Stone reporter following him around and painting a very negative portrait of his efforts.

Question 15

What film sees Brad Pitt play a World War II commander in love with a German spy?

Theoretically speaking, the last place one should look when seeking love is a battlefield, especially during one of history’s worst conflicts. Despite their better efforts, Brad Pitt’s Max Vatan and the woman he assumes to be a French Resistance fighter defy convention and fall in love, only for Vatan to quickly learn the other is not as she advertises. According to reports, his new wife is actually a German spy, a story he refuses to believe until they already have a daughter and happy life together.

Question 16

In which film does Brad Pitt’s family serve as a metaphor for the creation of Earth?

According to this metaphysical, high concept film, there are two ways for a person to live their lives: the path of grace, or the path of nature. For better or worse, Brad Pitt’s simply named Mr. O’Brien chooses the latter option, working at a job for which he has no passion and acting borderline abusive to his family, and especially his wife. Naturally, this leaves his boy more accepting of their mother, who chose the other option. On the plus side, eventually Mr. O’Brien realizes he made the wrong choice and seeks forgiveness.

Question 17

What film sees Brad Pitt as a husband with a strained marriage unwittingly involved in an international conflict?

Told out of sequence and featuring multiple interlocked storylines, it probably takes more than one viewing of this Golden Globe Best Picture winner for the average audience member to fully understand it. From the perspective of Brad Pitt’s Richard Jones, it’s basically about a family falling apart, although the fact they do so across three separate countries obviously makes things a tad confusing. He and his wife are in Morocco, while their nanny and children go from the U.S. to Mexico and back, all finding significant conflict along the way.

Question 18

Which film featured Brad Pitt as a writer experiencing icy relations with his wife?

The second of two films featuring Brad Pitt and his real-life wife Angelina Jolie as a married couple, this movie about a relationship falling apart was ironically shot during the pair’s honeymoon. For much of the film, it’s unclear why Pitt’s Richard and Jolie’s Vanessa aren’t getting along, aside from the fact they’ve been married quite a while, and the spark seems to be fading between them. Tensions grow significantly worse when a younger couple in a hotel room next to theirs seems to have everything they want, only for the tide to turn once they confront their true feelings.

Question 19

What movie featured Brad Pitt as an exercise trainer who discovers CIA secrets?

It’s been said there’s little in this world more dangerous than a simple mind with a small amount of important information, and that’s definitely the case when Brad Pitt’s Chad Feldheimer stumbles upon a CD filled with an ex-CIA agent’s memoirs. Granted, this information is virtually irrelevant to international affairs, yet he and a co-worker are convinced the disk contains top secret government files, setting forth a ridiculous farce that soon leads to his demise. On the plus side, he goes out with a massive smile on his face, still unaware what the heck is happening.

Question 20

In which movie did Brad Pitt play a legendary outlaw?

Many films are about men desperately attempting to leave their mark on the world, though only a small number of them manage to do so. In this revisionist Western, just about every character would indeed go down in history, most notably Brad Pitt’s title character. Of course, Casey Affleck’s other title character would also make a serious impact in gunning him down, and the nature of this act would leave both of them with unfavorable mentions in the average history book. Not that Pitt’s character would mind, having essentially orchestrated his own demise.

Question 21

What animated sequel sees Brad Pitt portray an adventurous shrimp?

Contrary to that old Hollywood adage that “there are no small parts, only small actors,” this CGI follow up sees two industry giants playing some of the tiniest animals in existence. Brad Pitt’s Bill is the more determined of the two, suddenly realizing just how bad he and his fellow krill have it at the bottom of the food chain. While his buddy Will is happy to go with the flow, Bill aspires for more, attempting to rise up the ranks and become a predator. This quickly proves more dangerous than expected, at least to the little crustacean’s big mind.

Question 22

Which film features Brad Pitt as a spree criminal with a younger girlfriend?

Most people studying and reporting on true crime likely have just a touch of intrigue when it comes to the criminals they write about, yet there’s a limit to how far they would go chasing a story. Even as Brad Pitt’s darkly charismatic Early Grayce begins revealing his true nature in this film, psychology grad student Brian Kessler remains highly interested. The fascination doesn’t even let up until the point where he and his girlfriend finally realize they’re in grave danger for daring associating with him.

Question 23

In which animated film does Brad Pitt play a defeated former superhero?

Flipping the script on both superhero films and the idea a huge actor like Brad Pitt should spent as much time in the spotlight as possible, this film sees his heroic character Metro Man fall victim to his arch nemesis almost immediately. Well, that’s what audiences are lead to believe, anyway, as he reappears near the end of the action, revealing he was simply tired of the lifestyle and wanted to pursue a secondary career in music. Ironically, Metro Man’s absence removes any meaning from his enemy’s life, turning the former villain into Metro City’s next big hero.

Question 24

What film saw Brad Pitt play an iconic literary bloodsucker?

Long before vampires were more or less the coolest characters in pop culture, Brad Pitt’s Louis du Pointe du Lac was absolutely despondent over his bloodsucking condition. Representing the opposite side, his sire Lestat de Lioncourt gleefully accepts their fate, even adding a third member to their team in a young girl named Claudia to continue terrorizing the public. Naturally, this only saddens Louis further, especially after Claudia is turned to dust as retribution for trying to fight back against Lestat’s overbearing influence on them both.

Question 25

In what science fiction film does Brad Pitt portray a mental patient?

Special for several reasons, this next film lead to Brad Pitt’s first Academy Award nomination and first Golden Globe victory, and thus far remains the only one of his movies to get adapted into a television series. While his character Jeffrey Goines was definitely wild enough to catch attention from critics, the TV show was a bit of a surprise, considering how confusing the film gets. It’s hard to sum it up in just a few words, but basically, Goines is a mental patient who may or may not be responsible for a virus that wipes out most of humanity.

Question 26

Which movie features Brad Pitt in a minor role as a criminal’s roommate?

Unlike most Brad Pitt films, where even his more minor characters play a major role, his character Floyd is decidedly minor to the overall action of this Tony Scott directed, Quentin Tarantino written cult classic. His only real role is serving as the slacker roommate of a much larger character, providing much of the intense action’s comic relief as quickly as possible. He only appears for a few short minutes, spending most of it laying down, even as his friend’s mob acquaintances make their way into his modest apartment.

Question 27

In what film does Brad Pitt play a child criminal turned district attorney?

The average film takes place during a short amount of time, only giving audiences a brief glimpse at the everyday lives of its characters. This next film takes a very long journey, forcing Brad Pitt to share the role of Michael Sullivan with then child actor Brad Renfro. As a preteen, the character is a would be gangster, only to (slightly) reform as an adult and rise through the legal ranks as an attorney. Once his old friends get on the wrong side of the law, though, he returns to his old tricks and ensures they maintain their freedom.

Question 28

Which movie sees Brad Pitt portray the Grim Reaper?

Arguably the highest concept film Brad Pitt has yet to appear in, this film sees him portray none other than the Grim Reaper, the living embodiment of the idea that all people one day will see their lives come to an end. Of course, he’s not exactly evil. Quite the contrary, the Bringer of Souls is apparently a bit of a romantic, choosing to live as a human for a short while and learn what it is he’s been tasked with destroying. Learning about love makes him regret his calling, but not enough that he’s able to reject it.

Question 29

What film features Brad Pitt as a bare-knuckle boxing champion?

The first mistake a two-bit boxing promoter made when hiring Brad Pitt’s Mickey O’Neil to throw a match was ignoring his nickname. With a moniker like “One Punch,” it should have been pretty obvious the guy was a born winner, and indeed, during the fated bout, he knocks out his opponent as quickly as his name would imply. All that said, maybe it wasn’t that much of a mistake, since Mickey has a few tricks left up his sleeve that allow him to win a second bout and help his promoters steal a valuable diamond at the same time.

Question 30

In which film does Brad Pitt play a man who uses fishing to bond with his family?

Every family has their own method of bonding, and chances are the Maclean brothers aren’t the only folks in Montana who come together through the sport of fishing. Brad Pitt’s Paul and his brother Norman don’t have much else in common, with the former representing the traditional wild child while the latter adheres to their father’s strict moral code. As often happens in these scenarios, Paul is also the better athlete of the two, able to snare massive sea creatures that his more demure brother could never wrangle.

Question 31

What film sees Brad Pitt portray a detective stuck in a literal cartoon universe?

Several years before he would ever lend his voice to a cartoon character, Brad Pitt took a different approach to the idea by appearing in this unique blend of live action and animation. His character Frank Harris starts out in the human world, only to quickly get transported to one filled with living cartoons. Shocking as this must be, he quickly resumes his previous role as a detective, and even begins to fall for one of the doodles who lives there, despite the fact relations between them is strictly prohibited.

Question 32

Which film features Brad Pitt as the middle child of three brothers in the Canadian Expeditionary Force?

Life rarely turns out the way people expect it will. Brad Pitt’s Tristan Ludlow is without a doubt the wildest of Colonel William Ludlow’s children, once fighting a bear when he was only 12 years old. Despite this reckless spirit, his main goal in life is protecting his brothers and sister, all of whom are much more reserved than he. Nonetheless, he’s also the one brother who hesitates when joining the Canadian Expeditionary Force, and he unsurprisingly doesn’t take it very well when one of his siblings doesn’t survive.

Question 33

In what movie does Brad Pitt play a captured espionage agent?

Every single movie about spies makes it abundantly clear just how dangerous the profession can get when things go wrong. Brad Pitt’s Tom Bishop especially learns this lesson when captured by the People’s Liberation Army prison in China, facing the threat of execution. Because tensions were already icy between his nation and the one that holds him as a political prisoner, there’s a good chance they wouldn’t bother saving him if not for an old friend in the CIA, portrayed by Robert Redford, in some respects the Brad Pitt of his generation.

Question 34

What movie sees Brad Pitt cross the border looking for an antique gun?

For the many, many movies centered on guns and the people who wield them, few give as much attention to the weapon in question as this deceptive romantic comedy. It begins with Brad Pitt’s Jerry Welbach venturing through foreign land looking for an extremely valuable antique piece of artillery, which he plans to smuggle back to his homeland. He’s doing so as a favor for a mobster he inadvertently crossed, looking to escape his wrath. The mission is significantly compromised when Welbach’s girlfriend gets involved, although not until after she attempts to call things off between them.

Question 35

In which film does Brad Pitt portray Austrian explorer Heinrich Harrer?

Vast as his filmography has been, Brad Pitt has only played a small handful of real people, perhaps most notably Heinrich Harrer, a man who was highly influential to the life of the 14th Dalai Lama. Ironically, it was never his intention to even enter the Buddhist leader’s land, having recently escaped from a Prisoner of War camp, where he was likewise detained through a series of unfortunate coincidences. Despite this, once in the presence of the Dalai Lama, he begins to love the culture he represents, naturally experiencing great sadness when the land is invaded.

Question 36

What movie features Brad Pitt as a rocker with giant hair?

Looking at some of the biggest rock and roll musicians throughout history, it can occasionally feel like style is far more important to chart success than actual substance. If anything, Brad Pitt’s title character in this film is very much hoping that’s the case—he’s got the giant hair, flashy guitar, and expensive jackets, so he figures the only remaining piece to the puzzle is a nice pair of shoes, like the ones Carl Perkins used to sing about. Unsurprisingly, though, even after finding the proper footwear, Pitt’s character hasn’t quite unlocked the key to happiness.

Question 37

In which film does Brad Pitt portray a member of the IRA?

From a very young age, Brad Pitt’s Frankie McGuire was more or less destined to become a member of the IRA after witnessing his sympathetic father’s demise. Regardless of what triggered his desire, there’s no surprise to the fact this choice lead to a great deal of conflict, both for him and virtually everyone he encounters. The troubles grow deeper when McGuire heads to the U.S. under the alias Rory Devaney to steal missiles, which has dire consequences for retired cop Tom O’Meara and his family when they let the boy into their home.

Question 38

What period piece saw Brad Pitt become part of Greek history?

Distilling one of the most iconic and sprawling pieces of literature in history down to three short hours is a weighty task for any film. Brad Pitt nonetheless gave it his best shot as Achilles, a major character in Homer’s epic Iliad. Of course, they didn’t have time to document the entire war which the text documented, instead focusing solely on the relationship between Achilles and Agamemnon. If nothing else, this was indeed a key part of the struggle between two nations, as men fighting over a woman was already a cause de guerre even in Ancient Greece.

Question 39

Which high school film featured Brad Pitt’s first leading role?

Everything has to start somewhere, and for the career of Brad Pitt, it began with this late ‘80s dark comedy about a group of troubled teens. Pitt had already appeared in a few minor roles at this point, but this was the first time he had the top billing, portraying Dwight Ingalls, a basketball standout who soon gets accused of committing a serious crime. He didn’t do it, but the mere accusation embroils him in the real culprit’s life, soon bringing great danger to everyone he knows.

Question 40

What superhero sequel featured Brad Pitt in a cameo role?

Theoretically speaking, when a movie casts a name like Brad Pitt, they’re going to want him appearing in as many scenes as realistically possible. Choosing to instead do the exact opposite, in this comic book sequel, Pitt physically appears for all of a single second, during the brief moment when his otherwise invisible character the Vanisher suffers an untimely demise. Of course, in this highly ironic film, the entire point was to poke fun at Pitt’s immense fame by giving him a role that barely acknowledges his presence.

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