The Bizarre Movie Leonardo DiCaprio Banned His Fans From Watching

Leonardo DiCaprio is one of Hollywood’s biggest — and most acclaimed — leading men. Considered one of the best actors of his generation, he’s also highly bankable, with his movies usually making big bucks at the box office. What if we told you he has spent over two decades trying to keep one of his early films buried, though, for fear of what it might do to that bankability? And what if we told you that film also starred Spider-Man?

A young star on the rise

Back in the mid-‘90s, DiCaprio was a young star on the rise. He spent his days acting in projects such as The Basketball Diaries and his nights partying with his friends in Los Angeles, many of whom were also actors. In fact, one of his best pals was Tobey Maguire, who would become the first big-screen Spider-Man in 2002, and Kevin Connolly, who is now best known as Eric “E” Murphy in HBO’s Entourage.

A boom period for indie cinema

The ’90s was also a boom period for independent cinema. In this era, a batch of young directors decided they weren’t going to wait to be given the keys to Hollywood’s kingdom by major studios. Instead, they went out and made their own films — on extremely limited budgets — and then sold these pictures for big money after gaining buzz at places like the Sundance Film Festival.

A creative, low-key approach leads to success

Success stories of this period included Quentin Tarantino’s Reservoir Dogs, Richard Linklater’s Slacker, Kevin Smith’s Clerks and Doug Liman’s Swingers. These films all heavily relied on dialogue rather than visual spectacle, which made the movies appear more “real” than typical Hollywood pictures. Many of these indies took a slice-of-life approach, so it often felt like you were simply watching groups of friends hanging out.

Why don’t we try making one of these?

At some point, DiCaprio and his buddies looked at each other and realized they were already a group of young Hollywood types hanging out in L.A. If independent movies were proving both creatively fulfilling and commercially viable… why didn’t they try making one? Over the course of six shooting days in ’95 and ‘96, that’s just what they did — and the result was Don’s Plum. It wound up tearing the group apart.