The Leonardo DiCaprio Film He Regrets Making the Most

Leonardo DiCaprio’s first indie film, Don’s Plum, is a movie he probably wants to remain lost to time. Shot in black and white between 1995 and 1996 and directed by R.D. Robb, the film depicts a single night in the lives of a group of young people.

The film features Leonardo DiCaprio and his friend Tobey Maguire, and also includes performances by Kevin Connolly, Jeremy Sisto, and Jenny Lewis. It’s said that a lot of the dialogue was made up on the spot, and DiCaprio and Maguire each earned $575 per day for their work on the movie.

The movie ran into significant problems both during and after its creation. Sources say DiCaprio and Maguire didn’t want it released as a full-length film, believing they were initially told it would be a short.

In 1998, producer David Stutman filed a lawsuit against them, claiming they intentionally prevented the film’s release. He asserted that Maguire feared his unscripted performance revealed details about his private life.

Look, as a critic, I’ve followed this case closely, and DiCaprio was pretty adamant in court. He testified, and I’m paraphrasing here, that the whole idea was always a short film. He flat-out said there’s no way he’d just jam with friends for one night and accidentally end up with a feature-length movie. He insisted he never intended for it to be anything more than a short.

Producer Dale Wheatley explained that Leonardo DiCaprio didn’t want to release the project as a full-length movie, stating, “I can’t risk having a poorly received film come out right now.” Wheatley shared this information in an open letter.

In 2014, Wheatley released the film for free online at freedonsplum.com. However, it was taken down in January 2016 after Leonardo DiCaprio and Tobey Maguire filed a copyright claim.

I was really struck by Wheatley’s reaction to the removal, and he put it perfectly when he spoke to Fox News. He expressed deep sadness that, even with all the celebration of this actor’s incredible career, he’s choosing to essentially censor a film – one he was in twenty years ago, no less – and the work of other artists. It feels like a really heavy-handed move, especially in this day and age.

Although it had a troubled past, Don’s Plum finally premiered at the Berlin Film Festival on February 10, 2001. Critics were divided: Time Out New York praised it as the best film at the festival, but Variety called it an unpleasant and boring movie with a large cast.

In retrospect, the drama surrounding the film’s release and the legal issues it faced have drawn more attention than the actors’ work. For Leonardo DiCaprio, the film Don’s Plum is a difficult reminder of a project he wished had never been made public.

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2026-01-06 11:44