Finding ‘Don’s Plum’: We Watched The Lost Movie Leonardo DiCaprio And Tobey Maguire Don’t Want You To See

Don’s Plum
is something of an infamous “lost film,” or so those who know about it claim. It was shot in 1995-1996, and directed by R.D. Robb, an actor-turned-director best known for playing Schwartz in A Christmas Story. It starred a who’s who of hot young stars and their real-life pals, including Leonardo DiCaprio, Tobey Maguire, Kevin Connolly (E from Entourage), Jenny Lewis from Rilo Kiley, Ethan Suplee, Jeremy Sisto, Meadow Sisto (Captain Ron), Amber Benson from Buffy, and Heather McComb (Party of Five).

The film’s forbidden fruit mystique stems partly from the fact that it starred much of the “Pussy Posse” (the loose affiliation of former child actors and magicians known for hanging out with Leo, chasing tail, and not tipping, immortalized in a 1998 New York magazine profile), and partly due to the notion that Maguire and DiCaprio hated the film and/or producers so much that they kept it from being released domestically. It remains unreleased here almost 20 odd years later, unseen, until recently, outside of a few festival audiences back in the 1990s. A film must be pretty dangerous to cause such a kerfuffle, right?

Don’s Plum has been the object of a sort of cult fascination in entertainment circles dating back to at least 1997, with the Pussy Posse crew engaged in a sort of ongoing he said/he said fight with Don’s Plum producers David Stutman and Dale Wheatley. The details are mostly too tedious to recount here, but here are the bare bones, via The Guardian:

In 1998, two years after the film was completed, producer David Stutman filed a suit against DiCaprio and Maguire, alleging that the pair “carried out a fraudulent and coercive campaign to prevent release of the film” because Maguire feared his improvised performance “revealed personal experiences or tendencies”. The actors, for their part, claimed that Don’s Plum had been pitched to them as a short film and subsequently re-edited into a feature, with them as unwitting leading men. Eventually the case was settled, with Stutman agreeing not to release the film in the US or Canada.

And that was more or less that, until last month. That’s when Wheatley started a website,, which included a 6,000-word open letter to DiCaprio urging him to unblock Don Plum‘s release, along with a promise to post the film for free online.

Wheatley made good on his promise sometime in the past week. I managed to watch Don’s Plum during the relatively brief window before it was once again taken down, blocked thanks to a copyright complaint to Vimeo — the work of Maguire and DiCaprio’s lawyers, according to Wheatley.

The film was still up when I started writing this, and at the time I had no idea that this could become a historic document. Well, I’m ready, posterity.

The hook (at least for people who still wondered about Don’s Plum after it was buried) was that the movie supposedly made Tobey or Leo look bad. Per Decider:

…the largely improvised film paints the young, post-Titanic, Pussy Posse era DiCaprio in a very negative light — he goads women into discussing masturbation, dishes on having sex with hookers, and repeatedly describes women as “sluts” and “whores…”

Having watched it, I can tell you that it’s far more tedious than it is dangerous. Neither Maguire nor DiCaprio do anything any more embarrassing than the film as a whole, or being a young actor in general. It exists mainly as a rightly forgotten time capsule, a time crapsule, if you will.

The best way I can describe Don’s Plum is that it’s an attempted (read: failed) cross between Clerks, Kids, and those man-on-the-street interviews from HBO’s Real Sex.

Dialogue-heavy indies were cooler than cool in the early to mid 1990s, thanks to movies like Reality Bites, Singles, Clerks, Pulp Fiction, Kids, etc. — all of which helped create the perception — at least among people who didn’t quite understand why those movies worked — that if you could just capture some painfully earnest young people talking provocatively about sex and life, a compelling story would brew itself, like mixing sugar and active yeast

More than anything else, Don’s Plum is a product of that time, a kind of Swingers by way of the “Runaway Train” video, where extemporaneous riffs about masturbating meet teary confessionals about absentee dads (spoiler alert, all the characters had one). And all of it marinated in a sort of affected, non-specific angst.