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Actor Leonardo DiCaprio has been in many notable films. Now, he’s nominated for an Oscar for his performance in Quentin Tarantino’s Once Upon A Time In Hollywood. Has he worked with the famed writer/director before? Let’s find out.

DiCaprio stars in Tarantino’s ‘Once Upon A Time In Hollywood’

Leonardo DiCaprio and Quentin Tarantino at the photocall for 'Once Upon A Time In Hollywood' at the 2019 Cannes Film Festival
Leonardo DiCaprio and Quentin Tarantino at the photocall for ‘Once Upon A Time In Hollywood’ at the 2019 Cannes Film Festival | Stephane Cardinale – Corbis/Corbis via Getty Images

The movie is Once Upon A Time In Hollywood. Written and directed by Tarantino, it follows a man Rick Dalton (DiCaprio) in the year 1969. He starred in a popular TV Western but is unsure of his career trajectory from there on. Then, Sharon Tate (Margot Robbie) and Roman Polanski move in next door.

The film combines the real history of the Charles Manson murders with fictional characters like DiCaprio’s and Brad Pitt’s. It also Margaret Qualley, Timothy Olyphant, Al Pacino, and Dakota Fanning. Once Upon a Time In Hollywood had its world premiere at Cannes before its July 2019 U.S. release.

The film is nominated for multiple Academy Awards

Many of Tarantino’s movies have done well at the Academy Awards. Pulp Fiction got seven nominations and one win, while Inglourious Basterds earned eight nods and another win. Django Unchained received five nominations and two wins, and The Hateful Eight earned three nominations and one win. But this year is something special.

Once Upon A Time In Hollywood has a whopping ten nominations, the most of any Tarantino film. In addition to nods for the actors and Best Original Screenplay (which he’s won twice), the famed filmmaker is up for Best Director for the third time, an award he’s never won.

Have DiCaprio and Tarantino worked together before?

This isn’t the first time that DiCaprio has been in a Tarantino film. He first appeared in 2012’s Django Unchained. The film stars Jamie Foxx as the eponymous character, a man who, in 1858, finds himself making a deal for his freedom from slavery — only it’s not as easy as it sounds.

DiCaprio has a small but memorable role in the film as Calvin J. Candie, an unhinged and merciless plantation owner with whom Django is forced to negotiate. He wasn’t nominated for an Oscar for the role, which many found baffling, as he severely cut himself during a scene and continued filming.

Tarantino is said to be making just one more movie

Once Upon A Time In Hollywood is Tarantino’s ninth movie. And according to him, it’s his second-to-last. He has been saying for years that he only plans to make ten movies in his career.

Appearing on Jimmy Kimmel’s show back in 2015, Tarantino told the host, “If I only think that I only have two movies, well, that keeps it at the tip of the spear if you know what I mean. That means that those ones better be good and I better make everything about them. And I actually like that kind of focus.”

Tarantino is sticking with this plan, it would appear. “Doing the TV thing could be really kinda cool, but I kinda like the idea of making ten motion pictures then boom! That’s it, that’s done, the filmography is locked,” he told Kimmel in 2019. So unless DiCaprio is turning to the small screen, it looks like they won’t be working together again.

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