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Report: The Ugly Story Behind DiCaprio’s ‘Lost Film’ He Doesn’t Want You To See
Leonardo DiCaprio attends Sony Pictures' "Once Upon a Time ... in Hollywood" Los Angeles Premiere on July 22, 2019 in Hollywood, California.
(Photo by Axelle/Bauer-Griffin/FilmMagic)

In an exposé for The New York Post published Monday, Steven Greenstreet and Tamar Lapin peel the curtain back on the ugly, rather tragic story behind the banned and buried film “Don’s Plum” — the “lost” feature-length film that Leonardo DiCaprio and Tobey Maguire “fiercely fought for decades to keep it from seeing the light of day” and the failure of which left “ruined careers, destroyed friendships, divorce and thoughts of suicide.”

The film, Greenstreet and Lapin report, is a “Clerks”-esque, largely ad-libbed movie shot over a period of just six days in the mid-1990s starring DiCaprio, Maguire, and some of their other “skirt-chasing” Hollywood pals known as the “P*ssy Posse,” according to a 1998 New York Magazine piece on “Leo Prince of The City.”

The film, which both DiCaprio and Maguire maintain was supposed to only be a short film, was eventually stretched into a feature by producers Dale Wheatley and Tawd Beckman. But, according to the producers, when Maguire saw the final product, things went off the rails. The stars reportedly took action to make sure the film was “banned from ever being shown in the US and Canada.”

So why was Maquire and eventually DiCaprio so intent on making sure the film never got released? After reviewing court documents, footage of the actors’ depositions, and exclusively obtained images and other materials, Greenstreet and Lapin shed a little light on some of the dirty details.

The film “tells the story of a group of 20-something guys who gather every Saturday night at a Los Angeles diner the film is named for, each with a new girl,” the Post reports. DiCaprio plays a “rude, standoffish” character with a foul mouth, whose memorable lines include “Do you girls masturbate at all?” and “I’ll f***ing throw a bottle at your face, you g*ddamn wh*re” — a threat he follows through with.

Maguire, whose performance supposedly fails to keep pace with DiCaprio’s, reportedly “reveals his unusual masturbation habits” in a scene, which the actor managed to strongarm the producers to cut.

The main problem, according to Beckman, is that the film “is so free-flowing and it seems so natural, that an audience is gonna look at that, look at DiCaprio, look at Maguire and say, ‘Oh, that’s who they are.'”

“It’s for that reason that Wheatley, Beckman and others suspect DiCaprio and Maguire didn’t want US audiences to ever see their characters on the big screen,” the Post reports.

That’s not how DiCaprio and Maguire framed it in their depositions, however, insisting instead that the real issue is that they never intended the film to be a feature, agreeing to shoot it only as a short.

That argument is complicated by an incident reported by the Post. According to Wheatley, DiCaprio, initially “apprehensive,” watched a cut of the feature-length film and loved it. “Suddenly he was jumping out of his chair. He’s high-fiving all of our friends … Leo had done a complete 180,” said Wheatley.

It was ultimately Maquire, according to Wheatley, who strongly resisted the film, fearing it “would ruin his career,” and allegedly turned DiCaprio against the producers. “Tobey Maguire believed ‘Don’s Plum’ would just be a pile of crap, we weren’t going to succeed, Leo’s going to say ‘no’ … but that’s not what happened,” Wheatley told the Post. “There’s no way to make it stop now unless he creates a villain … and I am the mark for that.” (Read the full report here.)

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