Once Upon a Time in Hollywood Brad Pitt Leonardo DiCaprio


Sure, Brad Pitt is one of the biggest movie stars in the world, but he's not selfish. He loves to share the screen. The dream pairing of him and Leonardo DiCaprio makes Quentin Tarantino's "Once Upon a Time in Hollywood" kind of, well, a buddy comedy.

Here are some of our other favorite Pitt movie team-ups.

Leonardo DiCaprio in "Once Upon a Time in Hollywood" (2019)


Washed up western star Rick Calton (DiCaprio) doesn't really appreciate best friend Cliff Booth (Pitt) enough. He's Rick's stunt double, chauffeur, all-around-handyman and bucker-upper. Cliff's got it rough too (he's living in a trailer, not a Hollywood Hills mansion), but he's dealing with the end of his glory days better than Rick. A lot better.

George Clooney in "Ocean's Eleven" (2001)

Warner Bros.

The Danny and Rusty friendship is the heart of the "Ocean's" films. (Remember when they both got choked up over Oprah?) And fun trivia: This scene from the first film, where they plot out their big Vegas heist, takes place in the exact same real-life Hollywood location, Musso & Frank, as in "Once Upon a Time in Hollywood." They're even sitting in the exact same spot at the bar. Cheers.

Edward Norton in "Fight Club" (1999)

20th Century Fox

In this darkly funny David Fincher film we can't watch enough, Tyler Durden and "Cornelius" (as Norton's name badge reads at one of his support group meetings) have a very tricky, complicated relationship. Tyler is everything Norton's character wants to be: Handsome, stylish, anarchic, and a born leader. (Also, abs for days.) Together, they start Fight Club and blow stuff up. Including our minds.

Morgan Freeman in "Seven" (1995)

New Line Cinema

Freeman is William Somerset, the  jaded cop who's close to retirement, Pitt is David Mills, the eager young hot-shot who is in way over his head. Somerset tries to be the voice of caution and reason, but this case ends in ... well, one of the grimmest finales ever. Imagine a movie where the two just hang out, have dinner, do research, and nobody's loved ones get murdered. We'd still totally watch that.

Eli Roth in "Inglourious Basterds" (2009)

Universal Pictures

Aldo Raine (Pitt) and Donny "The Bear Jew" Donowitz (Roth) have the Third Reich on the run as they roam the German countryside, "killing Nat-zees" in Tarantino's so-not-based-on-real-events World War II film. Their Italian might be a little weak and their big plan a little reckless, but hell if it doesn't work.

Tom Cruise in "Interview With the Vampire" (1994)

Warner Bros.

Imagine getting these two superstars back onscreen today.  Cruise's casting as flamboyant blond vampire Lestat was widely criticized at the time (author Anne Rice objected strongly, then praised him when the film came out.) Louis is arguably Pitt's most passive role -- Lestat is the drama queen here -- but we enjoy watching them bicker and brood.

Jason Statham in "Snatch" (2000)

Screen Gems

We don't know what the heck Pitt's unintelligible bare-knuckle boxer Mickey is saying most of the time in this underrated Guy Ritchie film and neither does boxing promoter Turkish (Statham). But we know Mickey can fight and Turkish can talk his way out of just about any situation. And that's all that matters.

Jonah Hill in "Moneyball" (2011)

Columbia Pictures

Former baseball player Billy Beane (Pitt) is having a losing season as general manager of the Oakland Athletics. Can a radical new approach from a young Yale econ grad (Hill) change the game? In real life, this team changed the sport forever. And the movie earned Oscar noms for both Pitt and Hill.  Double play.

Frances McDormand in "Burn After Reading" (2008)

Not-too-bright gym employees Linda Litzke (McDormand) and Chad Feldheimer (Pitt) see a chance for some big money when a CD containing an ex-CIA agent's memoir falls into their hands in this terrific, lesser-seen Coen Bros. film. It's a pairing we absolutely love.