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The Banned Black-And-White Film Leonardo DiCaprio Regrets Filming

Back in the early 1990s, a younger and only slightly less famous Leonardo DiCaprio banded together with a group of his friends to work on a little black and white indie project called "Don's Plum." This little friend group included the likes of Tobey Maguire and Dale Wheatley — one of whom went on to become Spider-Man, while the other never made it into the public vernacular. According to Wheatley, his utter rejection from the inner sanctum that is Hollywood was entirely due to his close attachment with "Don's Plum."

And while it's not unheard of for projects to ruin a promising career, Wheatley never even had one. That's not a jab at his talent as a filmmaker, it's a statement of fact. "Don's Plum" was his first project, and, according to him, DiCaprio and Maguire did everything within their power to prevent it from seeing the inside of a movie theater. While the finer points alter depending on who's telling the story, it's true that DiCaprio vocally denounced "Don's Plum." It's also true that the fallout included lawsuits and counter lawsuits and unpleasant press coverage. 

So, why did DiCaprio seemingly regret filming "Don's Plum," and why did he fight so hard to bury it? Here's everything we know and, as previously mentioned, a lot of it is interspersed with speculation, so keep that in mind. 

Improv and sketchy legal decisions

The official reason that Leonardo DiCaprio and Tobey Maguire gave during the legal fallout as to why "Don's Plum" shouldn't be allowed to release was that their original deal only permitted a short film, not a full-length feature film, to be created from their performances. While it's important to note that DiCaprio and Maguire won that particular legal battle, it should be equally noted that, according to Dale Wheatley, who gave his version of events to the New York Post, the project was built on a foundation of verbal contracts and honest-to-god handshakes, so no evidence of the original terms exist.

If that weren't precarious enough, the whole thing was filmed primarily without a script. The actors essentially improvised all the dialogue. Now, no one needs to speculate as to what a group of young men improvised ... "Don's Plum" was screened at the 2001 Berlin Film Festival. In addition, the film, like everything, is available online for anyone to find, should they be dedicated enough to go searching. The content is, to put it bluntly, not family-friendly. This, more than anything else, is what Wheatley believes lead to the stars getting cold feet about the project. 

Interestingly, Wheatley believes that DiCaprio's first viewing of the final cut — yes, it was a full film at that point, too — was undeniably positive. Maguire's first viewing, however, apparently wasn't. Speculation suggests that the art he created would have represented him in a way that he did not wish to be represented. It's also considered possible that Maguire felt outshone by his friend in their project and did not wish to be seen as secondary. Regardless, Wheatley noted that DiCaprio's stance changed when Maguire was displeased.

One-sided fallout

By Dale Wheatley's account, Tobey Maguire handled his displeasure very poorly, stating that the rising star accused him of riding coattails to fame and of using the press to blackmail him into a project he didn't wish to be a part of. It was at this point that the lawsuits began, but even by Wheatley's own telling, neither DiCaprio nor Maguire initiated the court proceedings — Wheatley did. He believed that the stars were publicly scapegoating him for their own misgivings.

And that's essentially where the story ends. Wheatley lost the court battles, and "Don's Plum" never got an American release. Yes, it was screened once in Berlin and "leaked" on the internet (Wheatley admitted to the act), but that's it. DiCaprio and Maguire went on to achieve the careers that we know them for today, and Wheatley is exclusively known for reminding the world about his singular project every few years. Hilariously, reviews (such as this one from Uproxx) feel that "Don's Plum" is more forgettable than career-altering, so even if Maguire agreed to the film, it probably wouldn't have changed all that much.

Is it possible that DiCaprio sunk a man's career to benefit his friend? Sure. It would not be surprising to learn that a celebrity mishandled their power to squash something — or someone — they didn't like. Conversely, it would also not be surprising to discover that an ambitious beginner latched onto someone more successful to gain access to Hollywood's ingroup. The entire debacle could've been resolved far more cleanly if anyone in that original group had thought to get anything in writing.