Don’s Plum | Cinema Year One

Credit: Zentropa Entertainments

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Orla Smith

In April 2021, it was announced that Leonardo DiCaprio’s company, Appian Way, had bought the rights to produce an English-language remake of Another Round, with DiCaprio in talks to star. It was a huge eye roll moment. Of course Hollywood are sprinting to remake a film that was already incredibly accessible in its original Danish-language, having just won the International Feature Oscar, and already starring a blockbuster name: Mads Mikkelsen. Still, the move was completely in character for DiCaprio. It’s just another step in his journey to becoming the most boring A-lister in Hollywood.

There’s no safer choice for DiCaprio than stepping into Mikkelsen’s (superior) shoes. It’s a tried and tested role previously played in a film that has already been embraced by the great guiding hand of the Academy Awards. Oscar is the force that guides DiCaprio’s life: since the titanic (ha ha) success of James Cameron’s 1997 blockbuster, DiCaprio has only starred in one film that wasn’t directed by a past Oscar nominee, with the exception of Don’s Plum (which was filmed pre-Titanic but released afterwards). Danny Boyle’s The Beach (2000) hardly seems like an outlier though, as Boyle had already burst onto the scene with Trainspotting, and would later become an Oscar darling with Slumdog Millionaire. DiCaprio has been directed by Steven Spielberg, Clint Eastwood, Sam Mendes, Quentin Tarantino, Alejandro González Iñárritu, Christopher Nolan, Martin Scorsese (five going on six times), and let’s not forget, Woody Allen

You’ll notice a lack of women on that list — because if women aren’t embraced by the mainstream, then they’re not embraced by DiCaprio (unless they’re a supermodel under twenty five). The same goes for people of colour. The last woman who directed him, Agnieszka Holland (Total Eclipse, 1995), is a fascinating filmmaker that he’d never work with today, because the great work she continues to do repeatedly goes unrecognised by awards bodies and mainstream film discourse (Her excellent latest film, Charlatan, was the Czech Republic’s Oscar submission but failed to be nominated). 

DiCaprio’s desperation to maintain his status as the biggest, most beloved movie star in the world means he never risks compromising his star image by doing anything that could be considered a little different, a little unpredictable. As Dale Wheatley, DiCaprio’s former friend (and one of the filmmakers behind Don’s Plum [2001]) has noted, anytime controversial news about DiCaprio surfaces, he tends to just donate a large sum to charity in order to make the bad press go away. It makes one cynically wonder whether his much-touted environmental activism is genuine, or if it’s just another building block in his carefully constructed facade.

At the turn of the millenium, one film threatened to complicate that persona. 2001 saw the very limited release of Don’s Plum after a lengthy legal dispute spearheaded by Leonardo DiCaprio and Tobey Maguire. This issue of Cinema Year Zero is about periods of transition between one decade to the next; the transition between the ‘90s and the ‘00s took DiCaprio from mid-level stardom to the stratosphere. Don’s Plum was the debris. Shot in 1995, when DiCaprio was a name and an Oscar-nominee but not a megastar, this innocent little film — an amusingly terrible time capsule — ruined careers and friendships, all because a twenty-three-year-old movie star had too much power, and too much ego to use it wisely. And because Tobey Maguire is an asshole.

The film itself is a trifle. It’s a group of friends, the fabled “Pussy Posse”, getting together to shoot an improvised, one-location hangout movie in the style of Clerks (right down to the black and white photography). Don’s Plum is directed by R.D. Robb, a less-documented “posse” member who now works as a very-occassionally-employed actor and producer. The film stars DiCaprio and Maguire alongside real life friends Scott Bloom, Kevin Connolly, Jenny Lewis, Meadow Sisto, Marissa Ribisi, and Amber Benson. There’s little “plot” to speak of: a group of bros meet up at their favourite diner, Don’s Plum, where they’ve each brought a girl to show off to each other. They chat. The dialogue is mostly improvised. It’s pretty bad.

What’s interesting about Don’s Plum is everything except for the film itself. I’ll spare you the finest details of the years-long feud surrounding the film, because there’s a three part New York Post documentary on YouTube that lays it all out in great detail. In short: after the film was shot and while it was still in post-production, DiCaprio became the biggest star in the world, and Maguire’s career started to gather steam as well. The filmmakers couldn’t believe their luck that their first feature, made with almost no money, could now become a hit based on its star power alone. Surely audiences would gather to watch the star of Titanic in a broad comedy, even if his cringey dialogue included such bangers as “My dad commited suicide, bro!”

The stars weren’t so thrilled. Maguire, who was intent on building a wholesome, all-American boy screen persona, was determined to halt the film’s release lest his character’s foul mouth and casual misogyny taint his image. Maguire’s character is less horrible than DiCaprio’s, but he still comes off as pathetic: in his first scene he attempts to pick up multiple women at a bar, moving swiftly on to the next every time he’s rejected. Meanwhile, DiCaprio’s Derek is an outright villain, constantly using homophobic slurs, mocking and leering at the women in the group, and altogether acting offputtingly immature. DiCaprio reportedly howled with laughter when Don’s Plum was first screened for him and wholeheartedly endorsed the film (as if I wasn’t already seriously questioning his judgement). But Maguire eventually managed to manipulate DiCaprio over to his side in his quest to ban Don’s Plum, preying on DiCaprio’s anxiety that the film would complicate his meteoric success.

Ultimately, DiCaprio’s and Maguire’s anxieties about their image did irreparable damage to the careers of their peers. They filed a lawsuit against the filmmakers, who lost so much money in the process that the people who worked on Don’s Plum barely got paid. Writer-producer Dale Wheatley has spoken openly and often about how the fallout from Don’s Plum affected him: nobody in the industry will work with him because they don’t want to get on the wrong side of DiCaprio. Don’s Plum’s reputation as “the film DiCaprio doesn’t want you to see” is what makes it so fascinating. What in the film was so revealing, so damning, that concealing it warranted tarnished careers and years of dispute?

Don’s Plum makes DiCaprio look like your average, bratty, kind of sexually aggressive teenage boy — the kind we’ve all known and tried to avoid. While his character, Derek, isn’t exactly him — he’s intentionally written as the antagonist of the piece — the actors were encouraged to incorporate their own energies, and their improvised words, into the shoot. In the New York Post documentary, Dale Wheatley tells stories of a young DiCaprio picking up girls and begging his friends to let him have sex in their apartment, because he still lived with his mother. That’s the kind of twenty year old Leonardo DiCaprio was: more Superbad than Romeo. That’s the kind of twenty year old he plays in Don’s Plum. The DiCaprio we know today, who is intensely private and chooses nothing but the most respectable roles, would never reveal so much of himself on screen.

I don’t claim to know where Derek ends and DiCaprio begins — he plays up Derek’s villainy, but Derek still lives in the same place as DiCaprio, has the same friends, and is also an aspiring actor. The similarities lead to speculation, especially given Derek’s violent, leery misogyny and his homophobia. How could audiences fall for him as a romantic lead if they saw him berating Amber Benson (“I’ll fucking throw a bottle at your face you whore”)? Or if they heard him explain how “there are four orgasmic spots in your asshole, that’s why gay guys fuck like rabbits,” a line that DiCaprio demanded be cut out in the edit. As Wheatley muses, “I can only guess that [DiCaprio’s agents] thought it was either too salacious or maybe too revealing.”

Ultimately, it’s DiCaprio’s and Benson’s feud that sticks with me. It’s violent on screen, but according to the filmmakers interviewed in the New York Post documentary, it was also violent behind the scenes. The scene frames Derek as the villain of the piece: he turns on Benson’s Amy because she objects to his boorish behaviour, shouting her down until she crumples in her chair, weeping and angry. Amy leaves the diner, and the film, by storming out of the door, screaming in frustration, and throwing a shoe at Derek. The group laughs nervously along with Derek, happy to let Amy be a casualty of his frightening callousness if it means staying in his good books.

In real life, DiCaprio didn’t think Benson was a strong enough actress, so he wanted her gone — and what DiCaprio wants, DiCaprio gets. The filmmakers told him that the only way to kick Benson off the film would be to berate her in character and on camera until she left. DiCaprio’s callousness on screen was real, as were Benson’s tears, and the shoe she threw. It’s a microcosm of the story surrounding Don’s Plum: Derek utilises his social power to scare off Amy; DiCaprio used his to fire Benson; and then he did the same to the film itself. Don’s Plum crystalised for me what I find so unsettling about Leonardo DiCaprio. Imagine giving a reckless boy like Derek the power to determine the social capital of not just his group of friends, but the workers in an entire industry. The Amys of the world would be in dire trouble.