The Leonardo DiCaprio & Tobey Maguire Movie You Never Watched - And Why You Still Can’t
Over the years, Leonardo DiCaprio and Tobey Maguire have collaborated on a few films. The pair first shared the screen in This Boy’s Life (1993) when they were both just starting their careers as child actors. As they played friends onscreen, a real-life friendship bloomed, and DiCaprio and Maguire have remained close ever since. 33 years after This Boy’s Life, Maguire and DiCaprio shared the screen once more in The Great Gatsby (2013), Baz Luhrmann’s take on the F. Scott Fitzgerald novel of the same name.
While fans of the iconic Hollywood friends were likely thrilled by the on-screen reunion of Maguire and DiCaprio in The Great Gatsby, they may not be aware that another reunion occurred much earlier. The pair starred together in another film, but despite having the A-list stars’ names attached, you likely haven’t watched it and still can’t. Here’s what happened to the feature film starring DiCaprio and Maguire that never made it to your screen.
The Obscure Indie Flick Leonardo DiCaprio and Tobey Maguire Starred In
DiCaprio and Maguire’s most mysterious collaboration is in the indie film Don’s Plum (2001). Even aside from the release struggles, the movie was likely to remain obscure outside film circles. Filmed across six days on a budget of just $40,000, it was an experimental film based largely on improvisation. Don’s Plum was the brainchild of a young Hollywood friend group, including DiCaprio, Maguire, Kevin Connolly, Scott Bloom, R.D. Robb, and Dale Wheatley.
During a meet-up at DiCaprio’s home, the group conceived Don’s Plum based on a concept from producer David Stutman, inspired by the improvisational techniques of Mike Leigh. The film came together within days, filmed at a diner in Los Angeles with DiCaprio and Maguire improvising most of their lines. Robb directed, while Wheatley and Stutman produced. Wheatley later hastily wrote up a two-sentence contract for DiCaprio to sign to make his involvement in the film official.
The result is about what you’d expect from an ambitious indie flick made by a group of film enthusiast friends. Don’s Plum is a black-and-white drama that follows the exploits of a group of young friends who meet weekly at the diner, Don’s Plum. It’s an unfiltered, raw look at 1990s youth culture. Film critic Mike D’Angelo compared Don’s Plum to Kids (1995), and it's an understandable comparison as both are simple, disturbing, and eye-opening accounts of what youth get up to without parental oversight. However, reviews are scarce since Don’s Plum was never released in the U.S. or Canada, though it did premiere at Berlinale.
Why You Still Can’t Watch ‘Don’s Plum’
Don’s Plum started gaining steam in post-production. Wheatley and Robb tapped Maguire to film additional scenes over a few more days, and news of DiCaprio’s involvement had distributors vying for the film rights. However, everything screeched to a halt when DiCaprio and Maguire began contesting their agreement to the film and blocking Robb’s attempts to sell the rights. When post-production on Don’s Plum finished, it was a feature film, and this is where the contention arose.
According to DiCaprio and Maguire, they agreed to star in Don’s Plum as a short, experimental film rather than a full feature. They claimed the short was filmed as a mere favor to their friends and felt exploited when it was suddenly marketed as a feature film. In an open letter to DiCaprio, Wheatley claimed the agreement never distinguished between a short and a feature.
In 1998, producer Stutman filed a lawsuit against DiCaprio and Maguire for their attempts to block the film’s release. After a lengthy, costly legal battle, Stutman, DiCaprio, and Maguire settled the lawsuit, in which Stutman agreed that the film would be released only outside the U.S. and Canada. Over the years, Wheatley has attempted to bring Don’s Plum to U.S. audiences, including breaching the lawsuit by uploading the full movie on his website, freedonsplum.com, alongside an open letter appealing to DiCaprio and Maguire to reconsider their stance on the film.
In a feature for Vanity Fair, Wheatley suggested that some competitive thinking, desire for control, or fear of mediocre performances motivated DiCaprio and Maguire to block the film. The truth behind the matter may never be known. A he-said-she-said debate ultimately determined the fate of Don’s Plum, leaving what may have become an indie cult classic legally absent from the screen to this day.
