The Lecherous Ghost of Leonardo DiCaprio's 'Pussy Posse' Gets Resurrected

Image: Don’s Plum

A new docu-series from The New York Post, titled The Curse of Don’s Plum, reveals the apparent “true story” behind an unreleased ’90s film (Don’s Plum) starring Leonardo DiCaprio and Tobey Maguire that’s been banned in the U.S. and Canada. The Post’s three-episode series, narrated by Dale Wheatley—the original writer and director of Don’s Plum—spends an hour attempting to recreate DiCaprio and his Pussy Posse’s greatest failure to date: independent filmmaking. (Second only to their inability to creatively name their secret sex fraternity.) Here is what I know after watching both the movie (Don’s Plum) and the New York Post’s docu-series (The Curse of Don’s Plum): neither project was worth the time.

The Post, using interviews with the film’s director, producers, and writers attempts to resurrect a tragedy from the remains of DiCaprio’s film. The movie’s creators had meant it to be an experimental twist on the filmmaking process. The result? A jumble of mismatched scenes peppered with offensive language, homophobia, and misogynistic tropes. In one scene, DiCaprio, in character, mocks a restaurant patron with improv-ed “jokes,” calling her “fucking fat” and a “a huge tank.” He also makes an observation—“Everybody is gay now!”—after the film’s co-stars Jenny Lewis and Heather McComb kiss. In a particularly grim exchange, DiCaprio dons a pair of fake teeth and proceeds with an impression almost too banal to be described.

Unlike DiCaprio’s then soon-to-be-released Romeo + Juliet, the downfall of this film was not a Shakespearean epic on brotherhood and loss, as told by Wheatley throughout the Post’s three episodes. If anything, The Curse of Don’s Plum docu-series zombifies a tiresome brand of Hollywood machismo that defined the Pussy Posse’s early reign of terror.

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In the opening moments of the docu-series, Wheatley admits he’d always “fancied himself a writer.” In 1996, McDonald’s Happy Meal heir and writer Tawd Beckman conceived of a movie about a “group of friends who go to a diner late at night,” based on a drunken conversation he had with friends at a Denny’s. Dale Wheatley then completed the script, and a variety of pre-fame actors were brought on to flesh out the various roles: Tobey Maguire, Leonardo DiCaprio, Kevin Connolly, Scott Bloom, Jenny Lewis, and Amber Benson. The script was doctored up using a pile of post-it notes from which the actors would “riff on,” Wheatley explained, with improvised dialogue while seated around a booth at a real-life diner called Don’s Plum. (You can imagine, from the clip above, how well this worked out.)

The leads, Maguire and DiCaprio, were B-list actors at the time. In 1996, DiCaprio was a year out from Titanic, a movie that launched his 20-year career of frowning at the Academy Awards. Maguire, meanwhile, was best known for a middling performance in a horror movie about a demonic toy plane called Revenge of the Red Baron. This didn’t mean they were unknown to the media! Citing rumors of the group’s many sexual exploits, the tabloids had named this cabal—comprised of DiCaprio, Maguire, David Stutman, RD Robb, and hanger-on Wheatley—the “Pussy Posse.” Wheatley calls the nickname an “unfortunate term” placed on a group of young men acting in ways that every other young man in the ’90s would act. DiCaprio, branded the lothario of the group by media outlets for his public exploits around Los Angeles and New York City, was the most notorious of the bunch.

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According to The Curse of Don’s Plum, DiCaprio’s sex life was a frequent topic of conversation among friends, many of whom had their apartments broken into late at night by DiCaprio and his various girlfriends. (Still living with his mom post-What’s Eating Gilbert Grape, his only option was to take them through the back door at another person’s apartment.) Worse, the Pussy Posse had a song for when he would enter the room with a new, nameless woman! It went: “Oh Leonardo! Don’t shoot your load, bro!” (Some things haven’t changed since then, namely: DiCaprio is still having sex with women the same age he was in 1996 almost 25 years later.)

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The men who produced Don’s Plum recount one particular incident as their proudest moment on set. Sandwiched near the middle of the Post’s first episode is a story about Amber Benson’s exit from the project. Wheatley, who claims DiCaprio wanted Benson fired because she was a “weak actress,” devised a scene where he would ambush her with a fight at the titular diner. According to those involved, her emotions in the moment were “completely real,” and the fight led to her storming off set. The fight scene begins shortly after DiCaprio heckles the woman with his “huge tank” insult (as noted in this blog above). Benson’s character objects to the language, and DiCaprio’s character begins screaming. His improvised insults (backed by raucous laughter from the other men in the scene) include: “You piece of shit hippie cunt!” And: “I will fucking throw a bottle at your face, you fucking whore!” Benson’s character throws a single Birkenstock sandal at DiCaprio’s character, who returns the gesture by smashing a glass against the wall near Benson.

The film soon collapsed into itself, and the various mistakes of its first-time creators led to a massive legal battle that spanned three continents. None of the actors or producers ever signed a contract while shooting—something Wheatley describes as a side-effect of friends making cinema together. On one side of the battle were Wheatley and the extraneous producers who wanted the film released. On the other side sat Maguire and DiCaprio, who wanted it blocked in North America, Europe, and Asia. Having seen the full cut, Maguire’s agent feared his client’s performance would be overshadowed and mocked. DiCaprio’s team saw it as a potential blemish on his upcoming press tours for Romeo + Juliet and Titanic. As Wheatley proclaims in the second episode, a Hyundai commercial had made DiCaprio “huge in Japan.”

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In the docu-series, Wheatley claims that, in a meeting with the film’s producers in 1997, DiCaprio announced, “My agents run this town,” and “Your movie isn’t gonna be at Sundance.” Don’s Plum was then blacklisted, and its creators gathered to sue. By 1998, DiCaprio’s star power had eclipsed any other in Hollywood with the massive success of Titanic. The power it gave him to bend the industry to the Pussy Posse’s iron will allegedly extended into the two parties settlement talks. Another wild revelation: lawyers reportedly forced the editors of Don’s Plum to remove a scene where Tobey Maguire’s character admits he liked to finger himself while masturbating. In a deposition, Maguire claimed the improvised line was just for laughs. Wheatley speculates that his agent feared the moment would brand him as an effeminate weakling in the press. (Unfortunately, the Arch Wizard of the Pussy Posse’s lengthy monologue about the four orgasm points in a male’s asshole being the reason “Gays fuck like rabbits!” also did not make the final cut.)

Throughout the docu-series, Wheatley describes the loss of Don’s Plum as an artistic tragedy that deprived the American public of an independent masterpiece. He’d echoed this sentiment to Fox News in 2016:

“It saddens me deeply that in 2016 we witness the senseless oppression of film and art by one of America’s most beloved actors. While the world celebrates — and certainly Americans celebrate — his great achievements in cinema , he chooses to use an iron fist to suppress the work of many other artists including him in a film made 20 years ago.”

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Speaking to Vanity Fair the same year, Wheatley bemoaned the film’s censorship after DiCaprio blocked his Tumblr page hosting the original cut of Don’s Plum. I’m truly bewildered at any claim of universal appeal. The loss of this film has clearly haunted Wheatley. His marriage fell apart after the Berlin premiere, and he grappled with suicidal thoughts throughout the aughts. It’s also clear that Leonardo DiCaprio continues to abuse the enormous power he hold’s to keep this film from a wider release. But, in allowing Wheatley’s recollection of the film and its creation to go unquestioned, The Curse of Don’s Plum fails to contend with the story that lurks beneath the surface of the film’s failure: secret sex fraternities for the rich and famous have aged horribly. (Unsurprisingly, not a single woman involved was interviewed for this documentary.)

https://www.vanityfair.com/hollywood/2016/12/leonardo-dicaprio-tobey-maguire-dons-plum

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Both Leonardo DiCaprio and Tobey Maguire declined to participate in the making of the docu-series. Perhaps more prominent participation from the film’s other stars could have crafted the explosive exposé the Post teased. Instead, the zombified memory of the now-defunct Pussy Posse is allowed to shamble into the sunset while men make bold declarations of artistic integrity and the “American cultural landscape.” If anything, it certainly adds a new dimension to DiCaprio’s starring role in Tarantino’s Once Upon a Time in Hollywood. 

Correction: An earlier version of this piece misattributed Heather McComb and Jenny Lewis’ kiss to Meadow Sistow and Amber Benson. This post has also been updated to reflect that Dale Wheatley finished the script based on an idea by McDonald’s Happy Meal heir Tawd Beckman.

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