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You’ll Never See This Leonardo DiCaprio Movie, If He Gets His Way

Leonardo DiCaprio Movie: Leonardo DiCaprio’s film North America forbids that. This indie drama, in which Tobey Maguire also starred, has essentially no chance of ever being discovered.

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You'll Never See This Leonardo DiCaprio Movie, If He Gets His Way

You’ll Never See This Leonardo DiCaprio Movie, If He Gets His Way

The Big Picture

  • Despite being shot in the ’90s, the film Don’s Plum remains virtually unknown and is banned in the US and Canada due to legal battles and shattered friendships among the cast.
  • Leonardo DiCaprio and Tobey Maguire were initially enthusiastic about the film, which was supposed to be a short improvised comedy. However, DiCaprio later changed his mind and didn’t think it was good enough to be released as a feature.
  • The film faced distribution troubles, was dropped from the Sundance Film Festival, and Miramax rescinded their offer to buy it. Legal battles ensued, resulting in a settlement that restricted the film’s release to a few markets outside North America.

It’s safe to assume that few people have ever heard of a little film called Don’s Plum, and an even safer assumption that those familiar will never see it. At least that’s what co-stars Leonardo DiCaprio and Tobey Maguire would prefer. Shot on 16mm black-and-white film in 1995 and 1996, Don’s Plum continues to languish in cinematic obscurity nearly three decades later. While it’s screened in a number of markets outside North America, the film effectively remains banned in the United States and Canada as a result of legal battles, shattered friendships, and feelings of betrayal and seething resentment. So what went wrong, and why is Don’s Plum seemingly destined to be lost in time?

What Are the Origins of ‘Don’s Plum’?

Having moved to Los Angeles from Canada, aspiring filmmaker Dale Wheatley became fast friends with a circle of young actors that included Leonardo DiCaprio, Tobey Maguire, Kevin Connolly and R.D. Robb. Wanting to make a film together, the group began development on a comedy dubbed Last Respects. A dissatisfied DiCaprio lambasted the screenplay, leading writer and producer David Stutman to pitch the actor a different project titled The Saturday Night Club. Taking inspiration from Kevin Smith’s Clerks, the film would be a reflection of the filmmakers’ own experiences spending late nights seated around a restaurant table, smoking cigarettes, and chumming it up with friends.

Taken by the notion of Stutman’s idea, which was allegedly pitched as a short film that would give the actors free rein to improvise, DiCaprio agreed to a role in the film and his participation secured that of several other actors. Rather than write a full screenplay, it was decided the film would be broken down into generalized scenes and the actors would ad lib their own dialogue. After renaming the film Don’s Plum and securing a budget courtesy of producer Tawd Beckman’s father (one of the architects behind the McDonald’s Happy Meal), the film moved forward with no formally written contracts. According to Dale Wheatley, “We believed we were making a film with our friends and foolishly didn’t pay attention to the paperwork.”

What Was ‘Don’s Plum’s Behind-the-Scenes Drama?

With a cast and shooting location in place, Don’s Plum rolled cameras in July 1995. Though it was a quick shoot, the film’s production had its share of drama behind the scenes. Regarding the film’s directorial responsibilities, David Stutman remembers, “I’m not saying that R.D. didn’t have input, but had it just been R.D. directing it, it wouldn’t have come out the way it was. In reality, John Schindler (line producer) directed Don’s Plum.” Schindler has said of the experience, “Well I directed the director, kind of.”

The drama would also extend to some of the actors seated around the titular restaurant’s table. It’s been claimed that DiCaprio wanted one of his co-stars, Amber Benson, to be fired as he didn’t consider her a “strong enough actor.” The solution was to essentially write her out of the story by having DiCaprio’s crass character verbally harass her to the point that she’d no longer want to participate. According to Tawd Beckman, “So her getting upset at the table is real. And her throwing the Birkenstock at their head is real. She was actually upset. She was actually storming out.”

After two days of filming, and telling Dale Wheatley to “make me look good,” Dicaprio wrapped on Don’s Plum and left the set to go shoot Marvin’s Room. Several months later, the filmmakers decided to shoot additional scenes that primarily involved Tobey Maguire, ultimately amassing roughly 30 hours of material between the two shooting schedules. Struck by the realization they had enough footage to expand the project beyond that of a short film, the decision was made to assemble a feature-length cut. But not everyone was excited about that prospect.

Leonardo DiCaprio Didn’t Think ‘Don’s Plum’ Was Good Enough for Release

Months after completing work on Don’s Plum, Leonardo DiCaprio was dismayed to discover his collaborators’ intentions to turn the originally proposed short into a feature. During a 1998 legal deposition, the actor said, “I never had any intention of doing a feature film. The agreement had always been that this was a short film. I would never go in for one night and improvise with my friends and make a feature film. There’s no way I would ever do that.”

As an Oscar-nominated actor whose star was on the rise, it’s been surmised that DiCaprio simply didn’t think Don’s Plum was good enough to be released as a feature. Having shot a largely improvised film with friends, who were first time filmmakers, over the course of a single shooting day, one can infer the actor was concerned that a film of potentially questionable quality could have a negative impact on his career. Dale Wheatley confirmed this sentiment with, “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.'” While DiCaprio maintained a sense of hesitance over Don Plum’s trajectory, Wheatley and co-writer/director R.D. Robb moved forward with cutting together their new vision of the film.

An unwavering disapproval of Don’s Plum would also surface via Tobey Maguire after viewing a rough cut. Fearing that some of the raw dialogue and characterization he brought to his role could negatively impact an audience’s perception of him as an actor, coupled with the notion that his performance may have been overshadowed by that of DiCaprio’s, it’s theorized that Maguire and his manager worried the film could derail his career. Nonetheless, the filmmaking team proceeded and finalized a cut, fully intending to have Don’s Plum seen by powerful Hollywood players.

Seeking Distribution For ‘Don’s Plum’

Through line producer John Schindler, the filmmakers were introduced to Jerry Meadors, at the time a well-known executive at Paramount Pictures. The media-savvy Meadors issued a press release about the film in order to bring it to the attention of influential people all over tinsel town. As a result, an industry screening of Don’s Plum was scheduled for late June 1996.

Leonardo DiCaprio, fuming over the attention the film was getting in the press, reluctantly attended the screening. As fate would have it, it went fantastically and the initially hesitant DiCaprio voiced praise for Don’s Plum. Jerry Meadors recalls, “He loved it. He jumped up and down. He turned and spins in the air. And on the way out, he congratulated R.D. and he said, ‘Well, you said you were going to make a feature. I never believed you could, but you did it, and it’s pretty good.’ It was that simple.”

Following the film’s industry screening, a second screening took place at the offices renowned talent agency, CAA. Thrilled with what they saw, the agency made offers to represent the filmmakers. In addition to that good fortune, Miramax Films, perhaps the premier producer and distributor of indie films in the ’90s, was prepared to make an offer to buy and distribute Don’s Plum.

Two Disastrous Meetings

After once again receiving word that Tobey Maguire had concerns over the film, Dale Wheatley and R.D. Robb arranged a dinner meeting with the actor. Over macaroni and cheese and tofu wieners, courtesy of the actor, the conversation quickly went from cordial to chaotic. According to Dale Wheatley, “And finally Tobey loses it and comes completely undone. And he starts screaming, ‘I want Don’s Plum to burn!’ And it was just rage, pure unadulterated rage.” But for Maguire, the final straw was his perception that Paramount executive Jerry Meadors, along with Wheatley and director R.D. Robb, had intentions to wield the power of the press against the two lead actors and profit from their rising fame. Wheatley remembers Maguire screaming, “You’re gonna pit the press against fucking Leo? You would do that to your own friend?”

Not long after the tense dinner meeting, another get together took place and included DiCaprio, Maguire, Wheatley and Robb, among others. Once again, Maguire came out swinging with accusations, announcing his suspicion that the filmmakers were conspiring to weaponize the media against DiCaprio if spoke negatively about Don’s Plum. Wheatley remembers DiCaprio’s demeanor becoming increasingly bitter and hostile, and that the actor eventually broke down and said, “My fucking agents run this town, and they run Sundance, and believe me, that movie’s not gonna be in Sundance.” According to the embattled writer and producer, “We were all friends for three years at that point. These were deeply rooted friendships and in one day, all of those relationships were destroyed.”

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The ensuing drama surrounding Don’s Plum had dire ramifications for its chances of distribution. The film was suddenly dropped from the Sundance Film Festival, and Miramax rescinded their offer to buy it. In response to DiCaprio and Maguire’s efforts to prevent their film’s distribution, Dale Wheatley, R.D. Robb, David Stutman and Jerry Meadors filed a $10 million lawsuit against the actors, who promptly responded with a countersuit.

After a lengthy and continuously fraught legal battle, the two parties reached a settlement. As part of the agreement, the plaintiffs had to remove some of DiCaprio and Maguire’s particularly off color dialogue from the film, and Don’s Plum could only screen in a handful of European and Japanese markets. It would ultimately screen at the 2001 Berlin International Film Festival to a decent reception, with one reviewer writing, “Unfortunately, odds are you won’t be able to see it without buying the eventual video from overseas, as the court settlement with DiCaprio and Maguire prohibits any form of release in North America.”

The Obscure Legacy of ‘Don’s Plum’

When all was said and done, DiCaprio and Maguire went on to lucrative careers and reached a level of mega stardom in Hollywood, while those behind the camera were essentially blacklisted from the industry. To add insult to injury, producer Tawd Beckman’s father, the Happy Meal architect who supplied the filmmakers with tens of thousands of dollars to make the film, sued producer David Stutman in 2005 and owns the rights to Don’s Plum to this day.

Years after the events in question, Dale Wheatley has remained consistently vocal about his experiences before, during, and after the making of the film. After it made some rounds screening overseas, his financial compensation amounted to a measly $180 after hefty legal fees. Though his career in filmmaking effectively ended before it really began, Wheatley has never given up on Don’s Plum, and in 2014, he penned an open letter to Leonardo DiCaprio and created the website freedonsplum.com.

He also uploaded the film to the website, where it remained for roughly 16 months until, just before DiCaprio would win his first Oscar for The Revenant, Wheatley received a notice that read, “We have removed your video titled ‘Don’s Plum,’ previously available at Vimeo, in a response to a takedown notice submitted by Leonardo DiCaprio and Tobey Maguire pursuant to the Digital Millennium Copyright Act.” While the two actors haven’t spoken publicly about the film for many years, it appears they have no interest in loosening their iron grip on its accessibility.

Nearly 30 years after Don’s Plum was shot, it remains highly unlikely the film will ever receive a proper theatrical or home video release in the United States and Canada. What began as a creative exercise among friends, each brimming with ambition and hungry to tell stories on film, took an unfortunate and decidedly dark turn into the realm of pop culture obscurity. As is often the case in Hollywood, the story behind the story is infinitely more dramatic, compelling, and complex. Whether it was greed, dishonesty, or outright manipulation that served as the driving force behind Don’s Plum demise, one can assume that only those involved know the full truth surrounding the events in question, and the rest of us can merely speculate.

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