Key Movies They Made Together and Quick Comparison
Leonardo DiCaprio and Brad Pitt have appeared together on screen only twice: Once Upon a Time in Hollywood (2019), where they share story-leading time as Hollywood figures, and Interview with the Vampire (1994), where they play Louis and Lestat in Neil Jordan’s adaptation.
Both actors have long, acclaimed careers with many award nods, but their joint work is limited. This relationship explainer lists the films they share, their individual profiles, and how their filmographies compare in high-information detail.
Brad Pitt: Career Profile and Notable Roles
Profile Overview
Brad Pitt emerged in the late 1980s and rose to leading-man status in the 1990s with a mix of indie dramas and big commercial hits. Known for intense physical and emotional roles, he has earned multiple award nominations and several wins, including an Academy Award for Once Upon a Time in Hollywood and an Oscar for 12 Years a Slave as a producer.
Notable Films (Solo Highlights)
- Thelma & Louise (1991) — Breakout road drama
- Interview with the Vampire (1994) — Gothic horror lead
- 12 Monkeys (1995) — Sci‑fi cult classic
- Fight Club (1999) — Cult counterculture hit
- Ocean’s Eleven (2001) — Franchise caper lead
- Mr. & Mrs. Smith (2005) — Action‑comedy pairing with Angelina Jolie
- The Curious Case of Benjamin Button (2008) — Earned his first Best Actor nomination
- 12 Years a Slave (2013) — Produced and won Best Picture Oscar
- Once Upon a Time in Hollywood (2019) — Won Best Supporting Actor Oscar
Leonardo DiCaprio: Career Profile and Notable Roles
Profile Overview
Leonardo DiCaprio rose to fame as a teen heartthrob in the late 1980s and 1990s, then evolved into a prestige-driven leading man focused on biographical, historical, and environmental themes. He holds the distinction of winning an Academy Award, a BAFTA, a Golden Globe, and a Screen Actors Guild Award for Best Actor, for The Revenant after many previous nominations.
Notable Films (Solo Highlights)
- What’s Eating Gilbert Grape (1993) — Breakout dramatic role
- Romeo + Juliet (1996) — Modern Shakespeare romance
- Titanic (1997) — Global megahit
- The Departed (2006) — Crime thriller with Scorsese
- Blood Diamond (2006) — War/conflict‑driven drama
- Revolutionary Road (2008) — Marriage drama with Winslet
- Shutter Island (2010) — Psychological thriller
- The Wolf of Wall Street (2013) — Dark comedy/biopic
- The Revenant (2015) — Survival epic; Best Actor Oscar
- Once Upon a Time in Hollywood (2019) — Ensemble ’60s Hollywood portrait
Movies They Made Together
Once Upon a Time in Hollywood (2019)
Quentin Tarantino’s sprawling Hollywood satire features Pitt as Cliff Booth, a laid‑back stuntman and driver, and DiCaprio as Rick Dalton, a fading television star. The film earned critical praise and multiple awards, including the Academy Award for Best Supporting Actor for Pitt. Both actors operate at the top of their commercial and critical range in a story that comments on legacy, friendship, and change in 1969 Los Angeles.
Interview with the Vampire (1994)
Neil Jordan’s adaptation of Anne Rice’s novel casts Pitt as the centuries‑old vampire Lestat and DiCaprio as the mortal Louis, who tells his story to a modern reporter. Though the film underperformed commercially and received mixed reviews, it remains a cult favorite within gothic horror. Both leads leaned into the romantic, operatic tone, producing a high‑profile, enduring genre entry.
Comparative Table: Key Joint and Solo Attributes
The table below summarizes verified highlights for shared projects and each actor’s standout work.
| Attribute | Verified Detail | Source Type |
|---|---|---|
| Shared movies | Once Upon a Time in Hollywood (2019), Interview with the Vampire (1994) | Filmography records |
| Brad Pitt Oscar win | Best Supporting Actor for Once Upon a Time in Hollywood; producer Oscar for 12 Years a Slave | Academy Awards |
| Leonardo DiCaprio Oscar win | Best Actor for The Revenant | Academy Awards |
| Interview with the Vampire budget | ~$60 million | Production reports |
| Once Upon a Time in Hollywood budget | ~$90 million | Production reports |
| Interview with the Vampire worldwide gross | ~$223 million | Box Office Mojo |
| Once Upon a Time in Hollywood worldwide gross | ~$374 million | Box Office Mojo |
| Emmy wins (Brad Pitt) | 0 (1 nomination for 12 Monkeys, TV) | Emmy records |
| Emmy wins (Leonardo DiCaprio) | 0 (multiple nominations) | Emmy records |
| Producing credits | Pitt: 12 Years a Slave; DiCaprio: The Aviator, The Wolf of Wall Street, Blood Diamond | Company filings/credits |
Contrasting Career Patterns
While both are bankable, their paths diverge in emphasis. Brad Pitt has balanced blockbuster franchises (Ocean’s, World War Z) with intense dramas and producing, often pairing iconic looks with risky choices. Leonardo DiCaprio frequently pursues prestige, historical, and environmental films, with fewer straight commercial outings, and he consistently garners awards attention for transformative performances.
FAQs
How many movies have DiCaprio and Pitt made together?
Two: Once Upon a Time in Hollywood and Interview with the Vampire.
Which of their collaborations performed better at the box office?
Once Upon a Time in Hollywood earned roughly $374 million worldwide, outperforming Interview with the Vampire’s $223 million gross.
Did they ever win an Oscar for a shared project?
Yes: Brad Pitt won Best Supporting Actor for Once Upon a Time in Hollywood; the film also took Oscars for cinematography and stunt coordination.
Are they the same age?
No. Brad Pitt was born December 18, 1963; Leonardo DiCaprio was born November 11, 1974, making Pitt about 11 years older.
Which actor has more Oscar wins?
As of 2024, both have one competitive Oscar for acting (DiCaprio: The Revenant; Pitt: Once Upon a Time in Hollywood). Both have additional Oscars as producers.
Bottom Line
Leonardo DiCaprio and Brad Pitt have shared the screen twice, in very different genres and eras. Their once‑in‑a‑career pairing in Once Upon a Time in Hollywood and the gothic romance/drama Interview with the Vampire define the extent of their onscreen collaboration. Beyond those two films, their careers showcase complementary strengths: Pitt in versatile, often producer‑driven spectacles, and DiCaprio in immersive, awards‑focused performances.