Leonardo DiCaprio’s Biggest Career Regret: The Film He Wishes He Never Made

Leonardo DiCaprio has a film in his past that he probably wishes had never been made. The movie, Don’s Plum, was an indie drama filmed in 1995 and 1996, but it didn’t premiere until 2001 at the Berlin Film Festival.

The black-and-white film follows a group of young adults over the course of a single night and stars DiCaprio alongside his friend Tobey Maguire, as well as Kevin Connolly, Jeremy Sisto, and Jenny Lewis. Much of the movie was improvised, with DiCaprio and Maguire reportedly earning $575 per day.

The path to release was far from smooth. DiCaprio and Maguire objected to the film being turned into a feature-length project, claiming it had been pitched to them as a short film.

This led to a legal battle. In 1998, producer David Stutman sued the actors, alleging they had tried to block the movie’s release because Maguire was concerned his improvised performance revealed personal details.

DiCaprio explained in court: “I never had any intention of doing a feature film. The agreement had always been that this was a short film. I would never go in for one night and improvise with my friends and make a feature film. There’s no way I would ever do that.”

Producer and screenwriter Dale Wheatley echoed DiCaprio’s reasoning, saying, “Leo said, ‘Guys, I don’t want this to be a feature film. I can’t afford a bad feature film to go out right now.’” The lawsuit was eventually settled, with an agreement that Don’s Plum could not be released in the U.S. or Canada and that some scenes would be removed.

In 2014, Wheatley uploaded the film to the website freedonsplum.com for free streaming. It was taken down two years later after a copyright claim was filed by DiCaprio and Maguire. Wheatley defended the release passionately, writing in an open letter:

“This letter is about so much more than just a movie. It’s about bullying, censorship, and abuse of power. You and Tobey Maguire spat in the face of independent film and the community that helped get you where you are today. You are not bigger than art, Leo. You are not bigger than the films in which you act.”

He added, “In a single night in 1996, you made a series of hasty and wildly irrational decisions that hurt a lot of people. By abruptly cutting off all communication with me and RD Robb, you cut off your access to the truth.”

Wheatley also told FOX411, “It saddens me deeply that in 2016 we witness the senseless oppression of film and art by one of America’s most beloved actors. While the world celebrates — and certainly Americans celebrate — his great achievements in cinema, he chooses to use an iron fist to suppress the work of many other artists including him in a film made 20 years ago.”

Don’s Plum received mixed reactions when it premiered in Berlin. Time Out New York called it “the best film [I saw] in Berlin,” while Variety described it as an “unpleasant and tedious ensemble.”

It’s clear that Don’s Plum remains a controversial chapter in DiCaprio’s career. While he and Maguire wanted to protect their reputations, the film still has a place in indie cinema history, and the story behind its release highlights the tension between artistic control and creative collaboration.

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