Don’s Plum: the film Leonardo DiCaprio would rather forget

Now that Leonardo DiCaprio is best known for chasing Oscars like a South African prosecution lawyer, it’s easy to forget the days when he was a paid-up member of the Pussy Posse, a loose assortment of celebrity bros whose mission was – according to a notorious 1998 New York Magazine profile – to chase girls, pick fights and not tip the waitress. Alongside DiCaprio, other core members reportedly included Tobey Maguire, Kevin Connolly and David Blaine.

Today, the Pussy Posse is little more than a memory, but its legacy lives on in the low-budget indie film Don’s Plum. With an ensemble cast featuring DiCaprio, Maguire and a host of less prominent associates, the largely improvisatory film was originally envisioned as a showcase for the group, in which their characters would converge at a run-down Hollywood diner to compare notes on masturbation, harangue fellow customers and generally behave like young people do in movies they write themselves.

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. Fellow producer Dale Wheatley told Indiewire at the time that the film-makers “amicably agreed on the settlement and all parties are happy to put this misunderstanding behind [them]”.

Somewhere along the line, Wheatley must have had a change of heart, because last month he began streaming the film without charge on freedonsplum.com, alongside a 6,000-word open letter asking DiCaprio to withdraw his opposition and allow the film to be released Stateside. It remains to be seen whether Leo will find time in his busy mantel-clearing schedule to respond, but for the rest of us, Wheatley’s campaign is a good opportunity to revisit a true oddity of the 90s indie scene.

Whatever the truth of its production, Don’s Plum is as good a vehicle as any for DiCaprio’s innate flair as an actor. Freed from the self-consciously weighty air of his recent roles, he delivers a sparky and sinister turn seemingly without care for how he might come across. Now that even the raunchiest roles embarked upon by former child stars are focus-grouped and micro-managed to death, the adolescent impulsivity on display here feels positively daring. No wonder the film was an uneasy fit with the carefully orchestrated road to respectability that DiCaprio set out upon next.