The Dark Tale Behind “Don’s Plum”: DiCaprio, Maguire, and Hollywood Drama

Don’s Plum, a film largely forgotten in the annals of cinematic history, continues to cast a shadow nearly three decades after its production. Starring Hollywood heavyweights like Leonardo DiCaprio and Tobey Maguire, the film remains a whispered legend – a project caught in the quagmire of controversy, legal disputes, and bitter resentments. Here’s a look into the tangled web of ambition, egos, and disputes that ensnared the movie.

Leonardo DiCaprio & Tobey Maguire's Secret Film: Why 'Don's Plum' Remains Unseen in the US

Read More: Daryl Dixon's Spinoff Distinctly Differs from 'The Walking Dead' – And That's a Good Thing

The Genesis of ‘Don’s Plum’

Dale Wheatley, an aspiring Canadian filmmaker, found camaraderie in Los Angeles with emerging actors such as Leonardo DiCaprio, Tobey Maguire, Kevin Connolly, and R.D. Robb. A budding project, initially named Last Respects, was transformed into Don’s Plum – inspired by Kevin Smith’s Clerks and reflecting late-night banter and camaraderie.

With the promise of creative freedom and improvisation, DiCaprio agreed to be a part of it, drawing other actors into the fold. The film’s uniqueness was its absence of a formal screenplay. Instead, the plan was for the actors to ad-lib scenes based on a general plot. Wheatley, reflecting on this casual setup, admits their error in not formalizing contracts, stating, “We believed we were making a film with our friends and foolishly didn’t pay attention to the paperwork.”

Behind the Curtains of ‘Don’s Plum’

Production, though swift, wasn’t without its frictions. Disputes about directorial responsibilities surfaced, with line producer John Schindler’s role becoming pivotal. A particularly intense disagreement arose when DiCaprio allegedly wanted co-star Amber Benson removed, leading to real on-screen tension.

Leonardo DiCaprio & Tobey Maguire's Secret Film: Why 'Don's Plum' Remains Unseen in the US

While filming proceeded in two distinct phases, it soon became clear that the amassed footage was substantial enough for a feature film – a decision that would sow the seeds of discord among the cast.

Hollywood Stars in Distress

Leonardo DiCaprio, by then an Oscar-nominated talent, wasn’t enthused about the transition of Don’s Plum from a short film to a feature. “I never had any intention of doing a feature film… There’s no way I would ever do that,” he expressed during a 1998 legal deposition. Dale Wheatley hinted at DiCaprio’s apprehensions, revealing, “Leo said, ‘Guys, I don’t want this to be a feature film. I can’t afford a bad feature film to go out right now.'”

Tobey Maguire too expressed displeasure after a viewing, fearing negative public perception due to his raw performance. However, despite their reservations, the movie garnered positive attention in Hollywood, and a distribution plan was in the works.

Clashes, Lawsuits, and Broken Dreams

After a positive reception at screenings and interests from agencies and indie film producers like Miramax, things seemed promising. Yet, everything unraveled after two disastrous meetings. Wheatley recounted Tobey Maguire’s fury, claiming he shouted, “You’re gonna pit the press against fucking Leo? You would do that to your own friend?” Maguire and DiCaprio’s assertions that the filmmakers intended to use media as leverage against them would further deepen the rift.

Leonardo DiCaprio & Tobey Maguire's Secret Film: Why 'Don's Plum' Remains Unseen in the US

The disputes culminated in Don’s Plum being dropped from the Sundance Film Festival and Miramax pulling back from distribution. A messy legal battle ensued, resulting in an agreement that limited the film’s screenings to European and Japanese markets.

The Ongoing Mystery of ‘Don’s Plum’

While DiCaprio and Maguire rocketed to stardom, the core team behind Don’s Plum faced industry blackballing. Dale Wheatley, however, remained undeterred. In 2014, he even set up and uploaded the film, only for it to be taken down due to copyright issues.

Decades later, Don’s Plum still remains enigmatic, shielded from North American audiences. A project born from friendship and creativity ultimately became an emblem of Hollywood’s darker intricacies. As tantalizing as the tale behind Don’s Plum is, its true nature might remain forever shrouded in mystery, leaving us pondering on the fragile nature of relationships, ambition, and the relentless machine that is Hollywood.