32 of Brad Pitt's greatest movie movements

Brad Pitt, dressed in a white tuxedo next to Diane Kruger, in Inglourious Basterds
(Image credit: The Weinstein Company)

For so long, the name “Brad Pitt” has been synonymous with leading man success in Hollywood. With so many unforgettable movies under his belt, there’s little reason to argue why. But which movies actually feature his best silver screen moments of all time?

Born in Oklahoma and raised in Missouri, Brad Pitt was just two weeks shy of graduating from the University of Missouri when he did what any number of Hollywood hopefuls have done and will continue to do: He packed his bags and moved to Los Angeles. 

Beginning with minor guest roles in TV shows like Growing Pains, Dallas, 21 Jump Street, and the horror anthology series Freddy’s Nightmares, his fame grew in the role of a hunky hitchhiker in Ridley Scott’s 1991 drama Thelma & Louise. After starring in the 1992 picture A River Runs Through it directed by Robert Redford, Brad Pitt’s career took off like a runaway train – and it hasn’t stopped running since.

Renowned as a Hollywood hunk with a vibe made for magazines, Brad Pitt is also a formidable actor who can stir real feelings from the audience: Sympathy, envy, anguish, and so much more, Brad Pitt is the textbook definition of a movie star, and these 32 all-time best movie moments from his are, without question, why he’s been a major presence for decades.

32. A Simple Drink Order (Babylon)

Brad Pitt orders a drink in Babylon

(Image credit: Paramount)

In Damien Chazelle’s Babylon, which is less of a monument than it is a tombstone to Hollywood as it once was, Brad Pitt plays fictional silent film star Jack Conrad, who represents the peak of movie stardom in a bygone era. (In a lot of ways, Brad Pitt is basically playing himself.) In the movie’s opening scene set at a lavish mansion party whose degeneracy would make the people of Sodom blush, Jack Conrad coolly orders a very, very complicated drink order to a waitress who comes on a little too strong. But Jack doesn’t mind. “Jen, I’d always look your way,” he tells her. And that, ladies and gentlemen, is why he’s a movie star. 

31. Literally Any Time He Dances (Burn After Reading)

Brad Pitt dances in a skin tight athletic wear in Burn After Reading

(Image credit: Focus Features)

In the black comedy classic Burn After Reading from the Coen Brothers, Brad Pitt plays a numbskull fitness instructor named Chad who gets wrapped up in a blackmail scheme when he and his accomplice, his gym co-worker Linda (Frances McDormand) think they’ve stumbled upon top secret government secrets. (They’re just notes for a memoir.) At least twice, Chad dances both to signify mistaken triumph and to combat total boredom during a stakeout. Also who can forget when he gets on the phone to carry out blackmail with an angry John Malkovich on the other end?

30. “I Hope You See Things That Startle You” (The Curious Case of Benjamin Button)

Brad Pitt rides a motorcycle in The Curious Case of Benjamin Button

(Image credit: Paramount)

In David Fincher’s epic fantasy drama The Curious Case of Benjamin Button, Brad Pitt plays a man who ages in reverse. The middle of the film includes a beautiful montage of Benjamin Button, after having left his fortune to his true love and their daughter, traveling around the world and living a humble life in exotic places throughout the 1970s. Accompanying the scene is poignant narration by Pitt, where Button imparts wisdom to his daughter to “make the best of it.”

“I hope you live a life you’re proud of,” he says, “And if you find that you’re not, I hope you have the strength to start all over again.”

29. That’s Why They Call It Achilles' Heel (Troy)

Brad Pitt as Achilles in Troy

(Image credit: Warner Bros. Pictures)

Wolfgang Petersen’s Troy may not be the most faithful adaptation of the Iliad. But with Brad Pitt playing the famed hero of the Trojan War, the movie’s climax – kicked off by, what else, a wooden horse containing soldiers whose emergence begins the Sack of Troy – has Achilles square off with Paris (played by Orlando Bloom), the brother of the fallen Prince of Troy, Hector (Eric Bana). In an act of vengeance, Paris shoots an arrow through Achilles’ heel, weakening the otherwise formidable and far superior soldier. So, if you ever want to remember what that idiom is all about, remember Brad Pitt with an arrow through his ankle.

28. A Shocking Cameo (Deadpool 2)

Brad Pitt gets electrocuted in Deadpool 2

(Image credit: 20th Century Studios)

The whole point of the mutant superhero Vanisher in Deadpool 2 is that, well, you don’t see him. He’s invisible. But the punchline is delivered in the middle of the movie, when Vanisher – as a member of Deadpool’s start-up squad X-Force – meets a shocking demise in the first mission of the X-Force. After ignoring wind conditions, Deadpool’s idea for a cool entrance by parachuting is derailed when nearly all of the X-Force members die in horrible ways. Vanisher flies right into electrical wires, de-stabilizing his invisibility to reveal none other than Brad Pitt. Pitt indeed took two actual hours out of his day to shoot his cameo for the movie.

27. Getting Picked Up (Thelma & Louise)

Brad Pitt appears in a car side mirror wearing a cowboy hat and denim

(Image credit: MGM-Pathé Communications)

Brad Pitt’s biggest cinematic breakout role was as J.D., a smooth-talking hunky hitchhiker in Ridley Scott’s celebrated drama about two women who hit the road to Mexico after Thelma kills her attempted rapist. On the way, they meet Brad Pitt as J.D., dressed head to toe in cowboy denim and the biggest white cowboy hat you’ve ever seen. The white hat is just a decoy, though. As J.D. later reveals to Louise, he’s a convicted robber also on the run. So early in his career, Brad Pitt proves his movie star bonafides in the way he so confidently inhabits the part of a drifting stranger who has nothing on him but has everything to hide.

26. Falling From Space (Ad Astra)

Brad Pitt falls from space next to a satellite in Ad Astra

(Image credit: 20th Century Studios)

In James Gray’s stunning 2019 sci-fi Ad Astra, Brad Pitt plays Major Roy McBride, the son of a legendary astronaut long thought deceased. The movie deals with mysterious power surges that threaten to end all life on Earth, and it’s up to Roy to figure it out based on his strangely personal connection to them. At the beginning of Ad Astra, the movie sets up the harrowing dangers of the power surges by having Roy McBride – aboard a space station hovering just above Earth’s atmosphere – witness the destructive power of no power at all, as Roy falls who knows how many feet to the ground. Through Gray’s skillful direction, audiences practically feel like they’re falling down to Earth with Roy. And that’s just the beginning of the movie.

25. Phone Call From Dad (Babel)

Brad Pitt cries on the phone in a hospital in Babel

(Image credit: Paramount)

Alejandro González Iñárritu’s 2006 drama Babel, which weaves several storylines in different locations around the world, stars Brad Pitt as Richard, an American tourist in Morocco with his wife Susad (played by Cate Blanchett). Amid uncertainty about their life together, Susan is shot by a bullet fired on their bus. After just narrowly making it to a hospital, Richard calls home and is comforted by his son’s voice. From bearing a look of death on his face to utter joy, Brad Pitt shows why he doesn’t need killer speeches or sweeping cameras to prove why he’s so good.

24. Couples Therapy (Mr. and Mrs. Smith)

Brad Pitt and Angelina Jolie sit on lounge chairs in couples therapy in Mr. and Mrs. Smith

(Image credit: 20th Century Studios)

Doug Liman’s lively and sexy action-comedy from 2005 co-starred Brad Pitt and Angelina Jolie as a married couple who don’t realize they’re both spies until they’re assigned to kill each other. (The movie famously and inadvertently set up Pitt and Jolie to start dating, and then marry, to become one of Hollywood’s most powerful couples until their 2016 divorce.) The movie kicks off with an amusing look at their attempts to repair their relationship in couples therapy. Liman wisely frames the camera only on them, making sure we know that it’s their relationship that will be put to the limit in this send-up of spy thrillers and suburban living.

23. “No One Asks to Be Left Behind” (Babylon)

Brad Pitt, in Babylon, crying at the end

(Image credit: Paramount)

Of its many different narrative threads, Babylon chronicles the rise and fall of silent film star Jack Conrad, which Brad Pitt imbues immense pathos as a man stricken with fear over a changing world. That includes his relevance as a movie star, as the advent of sound has sealed his expiration date. In confronting writer Elinor (Jean Smart) over a negative piece, Jack isn’t given apologies. Instead, like a patient receiving grim prognosis from their doctor, Jack is told that while his celebrity status is over, his immortality has just begun via pictures that will touch future generations. While the scene owes plenty to Jean Smart and graceful monologue writing, Brad Pitt deserves credit too, holding his own with silent expressions – captured in tight, intimate close-ups – that speak volumes of pain and revelation.

22. Meeting with the Mob (True Romance)

Brad Pitt in a ratty t-shirt on a couch in True Romance

(Image credit: Warner Bros.)

Nothing summarizes the 1990s better than Brad Pitt listening to Soundgarden. In True Romance from director Tony Scott and written by Quentin Tarantino, Brad Pitt enjoys a supporting role as Floyd, the lazy, slacker roommate of Dick (Michael Rapaport) who unwittingly gives up the main characters’ location to mob hitmen who’ve arrived to find them. The stunning visual contrast between Floyd – with his shaggy Kurt Cobain hair, a white muscle tee, and a surfer’s voice – and heavily armed wise guys in boxy suits and ‘70s glasses is a composition that only a director like Tony Scott could capably pull off. And Brad Pitt is deeply entertaining as a guy completely unaware of the stakes of the situation.

21. Dealing With Holli Would (Cool World)

Brad Pitt and Holli Would stand together in a room in Cool World

(Image credit: Paramount)

Shortly after the success of Who Framed Roger Rabbit, famed animator Ralph Bakshi pitched to Paramount a live-action/animated hybrid horror movie. Through intrusive rewrites, the movie became Cool World, a darkly comedic adult-oriented film that mixes live-action shots and animated characters. Brad Pitt plays Frank Harris, a World War II veteran who finds a new career as a detective in an alternate reality of cartoon-like characters. In an early scene with femme fatale Holli Would, voiced by Kim Basinger and drawn in her likeness, Frank puts down her desperate advances. Brad Pitt was not yet a major star when Cool World was made and released, and you can tell he’s just a little uncomfortable acting with nothing in front of him. But that only makes Brad Pitt a true movie star in the making by how much the scene still works.

20. “Forever Took Too Long” (Legends of the Fall)

Brad Pitt, wearing long blonde hair, stands under the sun in Legends of the Fall

(Image credit: Sony)

It’s a moment that beautifully captures the unwieldy power of true love that can’t end happily ever after. In Edward Zwick’s epic drama that spans most of the early 20th century, Brad Pitt plays the swoon-worthy Tristan Ludlow, the middle son of a U.S. Army Colonel who grows up in remote Montana and enlists in World War I. Arriving home, Tristan reunites with the beautiful Susannah (Julia Ormond), who was once engaged to Tristan’s brother until he died in the war. The beginning of their short but meaningful romance begins in a scenic, sunlit garden; it’s impossible to tell what’s more radiant, the garden or the actors standing in it. Referencing a letter Tristan wrote her, Susannah tells him, “Forever turned out to be too long.”

19. One Big Rocket (Mr. and Mrs. Smith)

Brad Pitt holds a rocket on his shoulders in Mr and Mrs Smith

(Image credit: 20th Century Studios)

“You shouldn’t be able to buy one of these things.” Mayhaps that be Doug Liman’s stance on firearms? Regardless, the action-comedy Mr. and Mrs. Smith is loaded with unforgettable moments between Brad Pitt and Angelina Jolie, as a married couple on opposite ends of an assassination assignment. Before they actually know of each other’s involvement, the two take turns taking literal shots at each other in a desert. After taking a leak, Brad Pitt’s John Smith takes out a giant shoulder-mounted rocket launcher that he fires on his own wife. Unaware who he fired upon, all John has to say is: maybe people shouldn’t get to buy these things.

18. “You Like Dags?” (Snatch)

Brad Pitt in a trailer park in Snatch

(Image credit: Screen Gems)

It’s not Irish, it’s not English. It’s just, as small-time boxing promoter Turkish (played by Jason Statham) puts it, “it’s just Pikey.” In Guy Ritchie’s crime comedy Snatch from 2000, Brad Pitt makes an abrupt left turn as talented boxer and mama’s boy Mickey O’Neil. In one of his first scenes, Mickey introduces himself with a hilariously unintelligible speech that makes us all reach for the remote to turn on subtitles. After starring in mega-hits like Seven and the wildly influential Fight Club, seeing Brad Pitt take on a completely different vibe in Snatch was one of the ages.

17. Mickey’s Revenge (Snatch)

Brad Pitt faces down an enemy boxer in Snatch

(Image credit: Screen Gems)

After mobsters killed his dear ma for failing to throw an earlier fight like he promised, the proud Mickey O’Neil, played by a bloody, sweaty, and chiseled Brad Pitt, takes his revenge on them all by again refusing to throw another boxing match and instead capitalize on his own winnings. Never mind that Brad Pitt famously starred in Fight Club. It’s in Guy Ritchie’s Snatch where Brad Pitt has never looked cooler or more dangerous in hand-to-hand competitive combat.  

16. Beating Up Bruce Lee (Once Upon a Time in Hollywood)

Brad Pitt fights Bruce Lee in Once Upon a Time in Hollywood

(Image credit: Sony Pictures)

It’s a scene that stirred controversy and drew the ire of Bruce Lee’s daughter, Shannon Lee. But Quentin Tarantino’s magnus opus Once Upon a Time in Hollywood stars Brad Pitt in top form as Cliff Booth, the loyal friend, chauffeur, and stuntman to fading Western star Rick Dalton (Leonardo DiCaprio). In one of Cliff’s own gigs, on the set of the TV show The Green Hornet, Cliff challenges the legendary Bruce Lee to a one-on-one fight behind the scenes. The purpose of the scene is to establish Cliff Booth’s capability as a scrapper and ruthlessness, which will come much later when his home is invaded by Sharon Tate’s would-be murderers. While it’s disheartening to watch Bruce Lee (played by Mike Moh) get manhandled by Brad Pitt, it’s still an all-time moment in the canon of Brad Pitt’s silver screen history.

15. Lunar Raiders (Ad Astra)

A rover spins out of control on the Moon in Ad Astra

(Image credit: 20th Century Studios)

In the sci-fi film Ad Astra, mankind has colonized just enough of the Milky Way galaxy to have a small presence on all the planets and their moons. But on Earth’s Moon, the new frontier looks a lot like the Old West, with raiders lurking in the shadows waiting to take supplies. Such a thing happens early when Brad Pitt’s Roy McBride, while on his way to his next stop, is attacked by raiders. What can be best described as “Mad Max Fury Road in space,” Pitt survives by dodging zero gravity gunfire, hastily taping a puncture in his own suit, and using solar panels to outmaneuver his enemies. Lest you think Ad Astra is another sleepy sci-fi about spaceships and humanity, think again.

14. Rooftop (Spy Game)

Brad Pitt, with Robert Redford-like shaggy hair, sits on a rooftop in Spy Game

(Image credit: Universal)

In Tony Scott’s spy thriller, appropriately named Spy Game, Brad Pitt plays a CIA operative studying the ways of spycraft under the veteran Nathan D. Muir, played by Robert Redford. Besides the subtext of two generations of Hollywood colliding in a classic genre piece, the specifics of Pitt and Redford’s confrontation atop a Berlin apartment roof involves Pitt’s character flummoxed by Muir’s inhuman ability to treat people as chess pieces. To Muir, that’s exactly how you survive the so-called spy game. Their tense meeting on this roof, seen through floating and sweeping camera movement, implies so much about their precarious partnership.

13. Discovering Claudia’s Remains (Interview with the Vampire)

Brad Pitt cries in a dark well in Interview with the Vampire

(Image credit: Warner Bros.)

Brad Pitt sure loves starring in genre pieces that span decades, doesn’t he? In Neil Jordan’s adaptation of Anne Rice’s world-famous modern fantasy novel Interview with the Vampire, Pitt plays Louis de Pointe du Lac, who agrees to an interview about his life as a centuries-old vampire to a journalist in San Francisco. Louis was made into a vampire in 18th century New Orleans by the charismatic Lestat (Tom Cruise); at some point, they befriend a young girl, Claudia (played by a young Kirsten Dunst), who they also turn into an immortal vampire. Their mistake was turning her when she was a child, meaning as a vampire she never ages.

Little more than halfway into the movie, Parisian vampires who hold court in their underworld sentence Claudia to death by sunlight for the murder of Lestat. Bound by a coffin, Louis is helpless to save her, and by the next night, he discovers her body in ash. In this scene, Pitt proves that even vampires can cry.

12. One Hundred Nazi Scalps (Inglourious Basterds)

Brad Pitt as Lt. Aldo Raine, wearing his military uniform in Inglourious Basterds

(Image credit: The Weinstein Company)

Brad Pitt has never been more inspiring or masculine than as Lieutenant Aldo Raine in Quentin Tarantino’s World War II film Inglourious Basterds. As the head of the “Basterds,” Lt. Raine leads a black ops commando unit who work to instill fear in all Nazis. After an enthralling opening at a quiet French farm, the movie continues with the unforgettable introduction of Aldo Raine who delivers a stirring speech about how the Nazis “need to be dee-stroyed.” With a Tennessee twang and swagger in his strut, Pitt gives cold blooded justice a handsome new face.

11. Fight in Quiet Coach (Bullet Train)

Brad Pitt and Brian Tyree Henry sit across each other in a train in Bullet Train

(Image credit: Sony Pictures)

Almost every scene of Brad Pitt in the 2022 action film Bullet Train is a fight scene. But of all of them, easily the most entertaining is his close-quarters fight with Lemon (played by Brian Tyree Henry). On a speed train that runs through Japan, Pitt stars as an American assassin (codenamed “Ladybug”) tasked with transporting a briefcase full of money. In the “quiet car” of the train, Pitt and Henry conjure up both laughs and thrills in an inventive fight scene where being shushed hurts just as much as a haymaker to the face.

10. At the Ranch (Once Upon a Time in Hollywood)

Brad Pitt stands tall in Spahn Ranch in Once Upon a Time in Hollywood

(Image credit: Sony Pictures)

In one of the most unforgettable sequences in an all-time unforgettable movie, the golden sun of Los Angeles turns nefarious as Cliff Booth finds himself in the belly of Charles Manson’s cult. Upon driving the nubile Pussycat (Margaret Qualley) back to Spahn Ranch, Cliff insists that he pay a visit to George Spahn, its elderly owner, out of concern. Until the moment Bruce Dern turns around to tell him everything’s fine, Tarantino’s picture suddenly overflows with dread and darkness, an atmosphere not unlike a horror movie. How appropriate, considering the ranch houses one of the most fearsome cult leaders and his followers who’ve ever lived. Through it all, Brad Pitt marches across the screen like a benevolent gunslinger, his form-fitting shirt reading “Champion” designating him the hero in this hostile frontier town in the middle of nowhere.

9. Dinner at 7 (Mr. and Mrs. Smith)

Brad Pitt with a mouthful of questionable steak in Mr. and Mrs. Smith

(Image credit: 20th Century Studios)

After John Smith and Jane Smith finally learn the identities of their latest assignment – themselves – they find each other quite literally on opposite sides of the table. Before the bullets fly and car chases begin, however, this married couple sit down for a seemingly pleasant dinner. (We say seemingly, because suddenly John has to wonder whether the hearty stake his wife has cooked is actually poisoned.) Cheers to the movie’s sound design for cranking up the volume on their chewing, wine gulps, and the clanging of silverware that suddenly sound like blades being unsheathed. Knives out, indeed.

8. Poker With “Teen Beat Cover Boys” (Ocean’s Eleven)

Brad Pitt oversees a poker game with TV celebrities in Ocean's Eleven

(Image credit: Warner Bros.)

One of the most important scenes in Steven Soderbergh’s Ocean’s trilogy is a poker game that not only functions as a time capsule of early 2000s Hollywood fame, but precisely the easygoing vibe in all the Ocean’s movies. In the first film Ocean’s Eleven, a secret celebrity poker game is overseen by Rusty, played by Brad Pitt, who is present to teach a few beautiful magazine whippersnappers how to play to win. 

What makes the scene so great isn’t just because you’ve got Joshua Jackson, Topher Grace, and Hollie Marie Combs out of nowhere playing themselves, but the symbolism of a heavyweight like Brad Pitt surrounded by the next generation of Hollywood learning the ins and outs. In the DVD commentary, Matt Damon admitted that he and Edward Norton also hosted poker games with Hollywood up-and-comers to unofficially learn the ways of their exclusive world. All Soderbergh did, with the help of Brad Pitt, was bring that back to the screen.

7. “Don’t That Picture Look Dusty?” (The Assassination of Jesse James by the Coward Robert Ford)

Brad Pitt, as Jesse James, stands on a chair to clean a dusty picture in The Assassination of Jesse James by the Coward Robert Ford

(Image credit: Sony Pictures)

In 2005, Brad Pitt starred in Andrew Dominik’s epic Western drama The Assassination of Jesse James by the Coward Robert Ford. With its provocative title (based on a 1983 novel), what matters less is who or even how Robert Ford (Casey Affleck) kills the infamous outlaw Jesse James (Pitt), but the fact James knew it was coming and that – as history shows – that Robert Ford, with his brother Charley (Sam Rockwell) sought to capitalize on their infamy by staging reenactments. In the scene foretold by its title, James enters the living room of his home, where the brothers were waiting for him, gun in hand. Instead of fighting or fleeing, James simply points out a dusty picture above the mantle, and takes out a chair to stand and clean it. 

As the music of Nick Cave and Warren Ellis begins, Affleck and Rockwell’s Ford brothers exchange long glances about their imminent betrayal to Jesse James. James himself sees their reflection and lets it happen. Andrew Dominik captures Pitt’s face in close-up, a face that expresses both disappointment, heartbreak, and inevitability in the life of a black hat outlaw. 

6. "Welcome to Fight Club" (Fight Club)

Brad Pitt, as Tyler Durden, gives the rules of Fight Club to men in a dingy basement in Fight Club

(Image credit: 20th Century Studios)

It’s a monologue oft repeated, and Brad Pitt’s unforgettable delivery is the reason why. David Fincher’s revered but misunderstood satire Fight Club famously co-stars Brad Pitt and Edward Norton as two men (or so we think, ahem) who start an underground fight club as a form of group therapy for men. While the personality of Pitt’s so-called “Tyler Durden” draws in hordes of dudes and things escalate out of control, this part of Fincher’s film is where Tyler Durden and “The Narrator” (Norton) show how comfortable they’ve grown in their corner of the world. This all-time moment is enthralling due in large part to Brad Pitt, whose plain instructions are delivered with quiet ferocity. Ever since, we never forgot the first rule of Fight Club.

5. The Reveal (Fight Club)

Tyler Durden reveals his true nature to the Narrator in Fight Club

(Image credit: 20th Century Studios)

Spoiler warning for Fight Club, if you’ve somehow not seen it yet: The big twist of Fight Club is that Edward Norton’s nameless narrator and Brad Pitt’s charismatic and wolf-like Tyler Durden are, in fact, the same person. And they have been all along. In a hotel room, Norton’s character comes to this realization in an argument “with” Tyler, his androgynous fashion suggesting he was never a physical part of Norton’s world. With a cigarette between his fingers and an unflinching stare into Norton’s eyes, Pitt becomes more than a movie heartthrob, but the masculine aspiration of every 21st century male – at least, those who don’t know how to meaningfully engage with the very text they’re consuming. When Pitt says “I look the way you want to look,” it suddenly dawns on us why Fight Club has the guy from Legends of the Fall here in the first place. 

4. Meeting in the Middle (The Curious Case of Benjamin Button)

Benjamin Button and Daisy gaze into the mirror of Daisy's studio in The Curious Case of Benjamin Button

(Image credit: Paramount Pictures)

Though Benjamin Button ages backwards, he eventually “catches up” with his beloved Daisy (Cate Blanchett). For a brief but beautiful time, they find themselves the same age. In Daisy’s dance studio, Pitt’s Benjamin Button – dressed in the most cozy cardigan you’ve ever seen hug a man – asks Daisy to join him in the mirror, to enjoy a moment of picturesque togetherness that they know is fleeting. “Wait,” he pleads, “I want to remember us just as we are now.” Little does Benjamin Button know it, but we are all trying to preserve this moment for eternity, too.

3. Reunion on Neptune (Ad Astra)

Brad Pitt, wearing a space suit, stares up to see his father in Ad Astra

(Image credit: 20th Century Studios)

Never meet your heroes. In Ad Astra’s case, never meet your dad. At the end of Ad Astra (spoiles!), Brad Pitt’s Roy McBride finally reunites with his estranged dad, H. Clifford McBride (Tommy Lee Jones). While most of the movie features characters talking up the legend of Clifford, what audiences see is a far cry from that mythological figure. Instead, Roy is forced to confront a paranoid, disheveled old crank who has killed his own crew to punish their mutiny. Clifford has been to the edge of known space and frightened by the nothingness before him, and has abandoned his humanity in the process. To see Brad Pitt’s face, framed so intimately by director James Gray, is to see the face of heartbreak.

2. Morning Coffee (Meet Joe Black)

Brad Pitt, wearing a shirt and tie, leans over a counter while drinking coffee in Meet Joe Black

(Image credit: Universal Pictures)

We’ve all felt a spark in the unlikeliest of places before. In Meet Joe Black, directed by Martin Brest, Brad Pitt stars as the physical form of Death who is inspired to live among humans and falls in love with a resident doctor, Susan (Claire Forlani). But before that, Pitt plays an unnamed guy in a coffee shop who has the most infectious and tender meet-cute with Susan. A mere hour before this handsome and charming man is violently killed by oncoming traffic, Susan and Pitt find themselves drawn to each other over a meaningful conversation about what forever is supposed to look like. When they part, they can’t help but look at each other. Though Meet Joe Black veers off into a wildly unexpected place afterward, this scene alone depicts what so many of us dream of when we think about meeting “the one.”

1. "What's in the Box?" (Seven)

Brad Pitt and Morgan Freeman stand in the desert at the end of Seven

(Image credit: New Line Cinema)

Next to Fight Club, no movie of Brad Pitt is as quoted as his futile question to serial killer John Doe (Kevin Spacey) in David Fincher’s dark psychological thriller Seven. Co-starring with Morgan Freeman, Brad Pitt plays a hot-shot, hot-headed homicide detective who teams up with a veteran officer (Freeman) to chase a serial killer who has been modeling his crimes after the Biblical seven deadly sins. Turn away now if you don’t want to be spoiled, but the twist ending of the movie reveals that John Doe has planned his last victim to be himself, a victim of “envy” towards Pitt’s David living a healthy, happy life with a beautiful wife (Gwyneth Paltrow). 

Doe’s stroke of evil genius is that the victim of envy is himself, and David is the victim of rage. He knows that when David opens the box containing his wife’s “pretty head,” he’s going to pull the trigger. It’s one of the darkest twist endings in Hollywood movie history. It not only catapulted everyone involved to stardom, including Brad Pitt, but it left us forever remembering our sins. Thanks, Brad Pitt!

Eric Francisco

Eric Francisco is a freelance entertainment journalist and graduate of Rutgers University. If a movie or TV show has superheroes, spaceships, kung fu, or John Cena, he's your guy to make sense of it. A former senior writer at Inverse, his byline has also appeared at Vulture, The Daily Beast, Observer, and The Mary Sue. You can find him screaming at Devils hockey games or dodging enemy fire in Call of Duty: Warzone.