Leonardo DiCaprio and Tobey Maguire’s Offensive and Misogynistic Movie: Don’s Plum Lawsuit Explained

If you thought Leonardo DiCaprio and Tobey Maguire were only Hollywood’s golden boys, think again. Don’s Plum, shot in the mid-90s but buried under layers of legal battles, reveals a much darker and controversial side to their early careers. Note that the film has been effectively banned in the United States and Canada for nearly 30 years, locked away because DiCaprio fought tooth and nail to keep it that way. 

Why was Don’s Plum buried? Reports point to its crude, off-color dialogue and a bitter legal feud. DiCaprio and Maguire were part of a loosely improvised project initially pitched as a short film, but when it ballooned into a feature, tensions exploded. 

Wheatley, the director, recalled DiCaprio’s concern (via Collider): 

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.’

Yet, after a surprisingly successful screening, the film seemed poised for success until Maguire’s furious backlash. Wheatley recalled:

Tobey loses it and comes completely undone… 

The clash culminated with DiCaprio declaring, “My f**king agents run this town, and they run Sundance, and believe me, that movie’s not gonna be in Sundance.” The fallout was swift: the film was reportedly pulled from festivals, Miramax withdrew, and a $10 million lawsuit war ensued. Today, Don’s Plum survives only in limited showings!

Real Truth Behind the Lawsuit That Buried Leonardo DiCaprio & Tobey Maguire’s Controversial Film




Don’s Plum was never meant to be more than a quirky, impromptu short. But after a mere six days of filming, the raw footage was unexpectedly enough for a full-length film. This caught Leonardo DiCaprio off guard. Despite initially dismissing the project, he later praised the film after a screening at MGM Plaza, telling collaborators (per Collider): 

I never believed you could, but you did it, and it’s pretty good.

But this positive momentum unraveled when Tobey Maguire vehemently opposed its release. According to Wheatley’s deposition, Maguire’s reaction was rage-filled: 

He starts screaming, ‘I want Don’s Plum to burn!’

This emotional outburst set off a chain reaction. Maguire accused the filmmakers of exploiting DiCaprio’s rising star, while the latter reportedly leveraged his growing influence, effectively killing the film’s Sundance debut and scaring off distributors like Miramax. The ensuing legal clash saw Wheatley and producers suing for $10 million, while DiCaprio and Maguire countersued, claiming no one intended a feature-length release.

The lawsuit ended with a settlement that blocked Don’s Plum from North American release and required the removal of the actors’ risqué improvised lines, including some shockingly offensive dialogue that might make even the most hardened viewer wince. Ultimately, Wheatley pocketed a mere $180 after legal fees.

The controversy didn’t just stem from legal power plays. The film itself showcased a group of young actors behaving wildly, embodying the reckless, competitive, and often sexist culture of late-90s Hollywood. Known as ‘The Pussy Posse’ for their relentless woman-chasing antics and bar pranks, the group’s offscreen lives bled directly into Don’s Plum’s script (per Slash Film). DiCaprio’s infamous line, “Stop looking at me like that, I’ll f**king throw a bottle at your face, you goddamn w**re,” followed by laughter, captures the film’s tone.

With careers skyrocketing after Titanic and other hits, the two stars prioritized damage control over artistic freedom. Producer David Stutman argued in court that 

Maguire and his manager had determined that, in the film, Maguire did not come off as strong a ‘leading man’ as DiCaprio, and that some of the improvisational comments Maguire had made during the film revealed personal experiences or tendencies that would undermine the public image he and his manager were trying to project.

Following a meeting between all parties, DiCaprio’s bitter declaration about controlling agents sealed the fate of Don’s Plum.

Inside Don’s Plum Troubled Shoot and Why Leonardo DiCaprio Walked Off After Two Days

The story of Don’s Plum begins with youthful ambition but quickly devolves into behind-the-scenes chaos. Filming began in July 1995, with David Stutman as producer and a revolving directorial influence, mainly line producer John Schindler, who admitted (via Collider):

Well I directed the director, kind of.

Tensions were palpable on set. DiCaprio reportedly pushed for co-star Amber Benson’s removal, questioning her acting strength, which led to Benson’s real frustration boiling over during filming. After only two days, DiCaprio exited the project to shoot Marvin’s Room, leaving the filmmakers to continue mainly with Maguire.

Months later, the amassed footage, nearly 30 hours, gave birth to a feature-length cut. Thanks to executive Jerry Meadors’ press savvy, an industry screening was arranged in 1996, where DiCaprio’s initial apprehension gave way to delight. The second screening at CAA further stirred interest from big players, including Miramax.

But that’s when Maguire’s fury hit full force. The bitterness culminated at a group meeting where DiCaprio supposedly declared his agents’ power would prevent the film’s Sundance showing, effectively ending its distribution hopes. Meanwhile, producer Tawd Beckman’s father, who bankrolled the film, later sued over rights, and Wheatley’s filmmaking dreams were dashed. 

Do you think Don’s Plum deserved to be buried? Drop your hot takes below!