Finding ‘Don’s Plum’: We Watched The Lost Movie Leonardo DiCaprio And Tobey Maguire Don’t Want You To See

Don’s Plum
is something of an infamous “lost film,” or so those who know about it claim. It was shot in 1995-1996, and directed by R.D. Robb, an actor-turned-director best known for playing Schwartz in A Christmas Story. It starred a who’s who of hot young stars and their real-life pals, including Leonardo DiCaprio, Tobey Maguire, Kevin Connolly (E from Entourage), Jenny Lewis from Rilo Kiley, Ethan Suplee, Jeremy Sisto, Meadow Sisto (Captain Ron), Amber Benson from Buffy, and Heather McComb (Party of Five).

The film’s forbidden fruit mystique stems partly from the fact that it starred much of the “Pussy Posse” (the loose affiliation of former child actors and magicians known for hanging out with Leo, chasing tail, and not tipping, immortalized in a 1998 New York magazine profile), and partly due to the notion that Maguire and DiCaprio hated the film and/or producers so much that they kept it from being released domestically. It remains unreleased here almost 20 odd years later, unseen, until recently, outside of a few festival audiences back in the 1990s. A film must be pretty dangerous to cause such a kerfuffle, right?

Don’s Plum has been the object of a sort of cult fascination in entertainment circles dating back to at least 1997, with the Pussy Posse crew engaged in a sort of ongoing he said/he said fight with Don’s Plum producers David Stutman and Dale Wheatley. The details are mostly too tedious to recount here, but here are the bare bones, via The Guardian:

In 1998, two years after the film was completed, producer David Stutman filed a suit against DiCaprio and Maguire, alleging that the pair “carried out a fraudulent and coercive campaign to prevent release of the film” because Maguire feared his improvised performance “revealed personal experiences or tendencies”. The actors, for their part, claimed that Don’s Plum had been pitched to them as a short film and subsequently re-edited into a feature, with them as unwitting leading men. Eventually the case was settled, with Stutman agreeing not to release the film in the US or Canada.

And that was more or less that, until last month. That’s when Wheatley started a website,, which included a 6,000-word open letter to DiCaprio urging him to unblock Don Plum‘s release, along with a promise to post the film for free online.

Wheatley made good on his promise sometime in the past week. I managed to watch Don’s Plum during the relatively brief window before it was once again taken down, blocked thanks to a copyright complaint to Vimeo — the work of Maguire and DiCaprio’s lawyers, according to Wheatley.

The film was still up when I started writing this, and at the time I had no idea that this could become a historic document. Well, I’m ready, posterity.

The hook (at least for people who still wondered about Don’s Plum after it was buried) was that the movie supposedly made Tobey or Leo look bad. Per Decider:

…the largely improvised film paints the young, post-Titanic, Pussy Posse era DiCaprio in a very negative light — he goads women into discussing masturbation, dishes on having sex with hookers, and repeatedly describes women as “sluts” and “whores…”

Having watched it, I can tell you that it’s far more tedious than it is dangerous. Neither Maguire nor DiCaprio do anything any more embarrassing than the film as a whole, or being a young actor in general. It exists mainly as a rightly forgotten time capsule, a time crapsule, if you will.

The best way I can describe Don’s Plum is that it’s an attempted (read: failed) cross between Clerks, Kids, and those man-on-the-street interviews from HBO’s Real Sex.

Dialogue-heavy indies were cooler than cool in the early to mid 1990s, thanks to movies like Reality Bites, Singles, Clerks, Pulp Fiction, Kids, etc. — all of which helped create the perception — at least among people who didn’t quite understand why those movies worked — that if you could just capture some painfully earnest young people talking provocatively about sex and life, a compelling story would brew itself, like mixing sugar and active yeast

More than anything else, Don’s Plum is a product of that time, a kind of Swingers by way of the “Runaway Train” video, where extemporaneous riffs about masturbating meet teary confessionals about absentee dads (spoiler alert, all the characters had one). And all of it marinated in a sort of affected, non-specific angst.

Shot in funky black and white, that makes youthful skin glow and everything else wash out, the film opens in Jeremy Sisto’s weird van with leopard print seats. He’s in the process of kicking Amber Benson out of the car (“You were supposed to take me to Vegas!” she yells), because… he’s tired of talking about his life or something. He’s exasperated, yet cripplingly inarticulate, sort of a metaphor for the whole endeavor.

The gist of it is, he needs her out of his life. “I need… pleasure, and I need… to know that with… brute force, I got you out of my life, okay?” he says, using his foot to physically push her out the door. Then he drives off, never to be seen again for the rest of the movie.

Was he her boyfriend? Just a neurotic guy who picks up hitchhikers? We never find out. It’s a mystery why his character even exists, though it does set up one of the film’s central themes: obtuse improvisation. Which doesn’t convey much beyond a sort of all-purpose drama. We don’t know who they are or what happened between them, just that it was dramatic.

The next person we meet is Tobey Maguire, adorably doe-eyed and barely pubescent, looking like he’d get winded trying to bruise a tomato. He’s hanging out in some early ’90s nightmare of a jazz cafe, drinking coffee out of a massive So I Married An Axe Murderer-sized mug and listening to a group of cool black guys play jazz so terrible it’s almost performance art. The horn players just sort of screech randomly while the bass noodles hookless gibberish and the singer looks over the top of his sunglasses and vogues, being provocative. He literally just yells “Climax!” at one point. The waitresses are also part of the show, doing some kind of burlesque-y interpretive dance along to the music, while dressed like a cross between In Living Color fly girls and Robert Palmer back-up dancers. All the while, Tobey tries to get a succession of women to “come meet up with me and my friends at a diner.”

The film intercuts a few ill-fated pick-up attempts with close-ups of the Jon Spencer Art School Explosion (was this product placement?). At one point, one of the fly girls stands directly behind Maguire and his attempted conquest, singing at them, or at no one in particular. “He said he wanted to f*ck me,” she sings breathily, into her retro-hip Elvis microphone. “Not just f*ck me, but really… f*ck me.”

Is this magical realism? I don’t know what this is. The performer, incidentally, is named “Toledo Diamond.” Look up virtually anyone involved in this film and you’ll end up down some smoky rabbit hole of psuedo-celebrity, Stephen Dorff waving e-cigs at you while you tumble further and further.

After getting shot down a few times, Tobey strikes gold with the waitress, Juliette, played by Meadow Sisto, who agrees to go to the diner with him. This is the last thing her character actually does for the entire rest of the movie, even though she was technically present for all of it. I’m not sure why she’s in this movie either. Maybe there was Sisto quota? Anyway, she’s extremely pretty, in that senior-stoner-chick-you-fantasized-about-freshman-year kind of way.

Soon we meet some other hot young actors, in separate vignettes: Jenny Lewis and Scott Bloom, in the midst of some post-coitus, quasi-existential squabble. Leonardo DiCaprio’s character, a sleazy hustler type calling up ladies on his loser friend’s giant cell phone. Kevin Connelly, playing his patented Guy-Who’s-Just-Sort-Of-Regular-In-A-Bland-Way character, who picks up Amber Benson, the Sisto castaway, who’s now hitchhiking, in his Jeep.

Naturally, they all come together at Don’s Plum, a diner run by a guy in a smoking jacket named “Don Plum.” Intercut with scenes at the diner table are Dream On-style cutaways of the characters talking to themselves in the bathroom mirror. This is apparently meant to reveal some inner truth about their character. In Don Plum’s cutaway, he says to the mirror, “Hi, I’m Don Plum.”

Apparently the gang likes to pick up chicks and meet up at Don’s Plum, to show off said chicks to each other, like Pussy Posse show and tell. Maybe this was the “personal tendencies” Don’s Plum allegedly revealed? I don’t know.

Once they’re all together — Leo, Tobey, E, the waitress, the hitchhiker, Scott Bloom, and Rilo Kiley — they smoke a lot of cigarettes and aimlessly say “f*ckin'” and “bro” for an hour. However much you overuse “bro” in your frat-speak parody, I promise, DiCaprio and Connolly use it more. “Dramatic things” will occasionally happen, but events don’t combine or tie together in any way. They just sort of inflate and pop harmlessly, like air bubbles. No consequences, signifying nothing.

At one point, a fat lady walks by and Leo makes fun of her. The hitchhiker girl tells him to stop, so Leo calls her a “squatty piece of hippie sh*t c*nt.” She throws something at him and runs outside, where she smashes up E’s Jeep and runs off, never to be seen again. We never even see E discovering his own smashed-up Jeep.

At another point, Connolly gets propositioned by a high-powered lady producer he’d auditioned for, whom he calls “Spielberg with a pussy.” She’s so turned on by this off-brand, teacup James Dean that she begs him to come home with her and do the sex, only to leave him at the diner anyway. They promise to call each other, and then Connolly’s character recounts the entire scene, the one we just watched, to his friends. “Bro, it was crazy, bro! She was on my dick so hard!”

Before and after that, pointless conversation. Sample dialogue:

“Do you guys bathe every day, and, like, wash yourself with soap?”

“You know what I’m so sick of though? All that f*cking commercial grunge crap. It all sounds alike. It’s like the record companies that are promoting sterile music. I mean I love Nirvana don’t get me wrong but they weren’t the Beatles.”

“You f*ckin’ thinkin’ about something, bro?”

“My dad committed suicide, bro.”

It’s sort of like an R-rated, half-written Breakfast Club where none of the characters are relatable. Or a poseur-y Kids, where no one really does scandalous things, they just talk about doing them until you wish they would die.

Every once in a while the film flirts with being so bad it’s good, notably toward the very end, about an hour and 15 minutes in. After a failed tryst with DiCaprio, Jenny Lewis gradually becomes Don’s Plum‘s answer to Kelly from 90210. “My dad is gone. And my mom is a junkie. She sells her ass on the corner,” she tells the group, who seem like they couldn’t care less. Next she’s in the bathroom, pawing at the mirror and freebasing, blaming herself for a childhood molestation. “I was the one that came on to Uncle Jerry. I was the one that was curious.”

I would watch just that five-minute segment over and over for laughs. The rest of the film though, is mostly tedious and forgettable, kids acting out without much purpose. The actors have compared it to an acting workshop, and that’s mostly what it feels like, aside from a soundtrack (Phantom Planet, Rilo Kiley, The Coup) that I’m only semi-ashamed to say is pretty good.

If Leo and Tobey wanted Don’s Plum buried because they thought it made them look bad, they shouldn’t have bothered. Don’s Plum doesn’t make them look bad. It doesn’t even make the filmmakers look bad, not really. Mostly it just makes the ’90s look bad.

Vince Mancini is a writer and comedian living in San Francisco. A graduate of Columbia’s non-fiction MFA program, his work has appeared on FilmDrunk, the UPROXX network, the Portland Mercury, the East Bay Express, and all over his mom’s refrigerator. Fan FilmDrunk on Facebook, find the latest movie reviews here.

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