The Leonardo DiCaprio Film He Regrets Making the Most

Leonardo DiCaprio’s early indie film Don’s Plum is a project the actor likely wishes he could forget. Filmed between 1995 and 1996 and directed by R. D. Robb, the black-and-white drama follows a group of young adults over the course of one night.

The movie stars DiCaprio alongside his friend Tobey Maguire, with appearances from Kevin Connolly, Jeremy Sisto, and Jenny Lewis. Much of the film was reportedly improvised, with DiCaprio and Maguire earning $575 a day for their work.

The film, however, faced major complications before and after production. According to reports, both DiCaprio and Maguire opposed releasing it as a feature film, claiming it had originally been pitched to them as a short.

Producer David Stutman sued them in 1998, alleging they had carried out a campaign to block its release. He claimed Maguire was worried that his improvised performance exposed personal experiences.

DiCaprio defended his position during the legal proceedings, stating, “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 Dale Wheatley also shared his perspective, writing in an open letter, “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.’”

Wheatley later made the movie available for free streaming on freedonsplum.com in 2014. It was removed in January 2016 after a third-party copyright notice submitted by DiCaprio and Maguire.

Wheatley spoke out about the removal, telling Fox News, “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.”

Despite its rocky history, Don’s Plum premiered at the Berlin Film Festival on February 10, 2001. Reception was mixed. Time Out New York called it “the best film [I saw] in Berlin,” while Variety described it as an “unpleasant and tedious ensemble.”

Looking back, it’s clear the film’s controversial release and legal battles have overshadowed the performances of its stars. For DiCaprio, Don’s Plum remains a reminder of a project he never wanted to see released in the first place.

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