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It was a victory for cinephiles and snoops alike this morning as Don’s Plum, the notorious mid-’90s indie movie that Leonardo DiCaprio made with his “Pussy Posse” pals Tobey Maguire and Kevin Connolly, was made available to stream via Vimeo by the film’s producer Dale Wheatley. [UPDATE: the film has been taken down at the request of DiCaprio and Maguire.]

The long, fraught story behind the production of Don’s Plum — a black-and-white, largely improvised slice-of-scumbaggy-life movie about young friends convening at a local dive, exchanging sex talk and put-downs, and trying to score, filmed in a style that is alternately claustrophobic (the entire universe seems to exist inside the same awful back-room jazz club) and amateurish — included a 1998 lawsuit, the result of which was that the film could only be released outside the United States and Canada. The story was that DiCaprio and Maguire didn’t want the film to be seen, for whatever reason. The assumption was that they thought it would be detrimental to their fast-rising careers. Even though the movie’s been taken down, it’s work clicking over to freedonsplum.com to read producer Dale Wheatley’s lengthy account of the dispute/open letter to Leo.

Having finally seen the film, you can see what DiCaprio is talking about … sort of. The film doesn’t put any of the actors in the best light, and DiCaprio’s character is the most vulgar, misogynist, homophobic, and loathsome of anyone we see on screen. These are characters, of course, and DiCaprio has played plenty of terrible ones, but the fact that real-life friends DiCaprio, Maguire, and Connolly were so infamous for that Pussy Posse article in New York Magazine, the lines between fiction and reality understandably start to blur. And that’s exacerbated by the heralded fact that the bulk of the movie was improvised in a single night.

In the wake of Titanic, Leo-mania was real, and no matter how small and outside the mainstream Don’s Plum was, it certainly would have been uncovered by his rabid fans in 1998, and perhaps the persona that Leo puts on in the film would have put a dent in his teen-idol armor. Still, it’s hard to watch Don’s Plum and not think that the boost to his indie cred wouldn’t have been worth it. The movie plays like a navel-gazing L.A. answer to Kids, where The Youth of America are shown to be venal, sex-obsessed little monsters. That DiCaprio and Maguire are still opposed to its distribution enough to get it yanked off of Vimeo in under a day speaks volumes, but I’d still love to know what Leo finds so shameful about the movie that he doesn’t want it seen.

My five top contenders:

The scene early on in the film where Leo’s character unloads on a character played by Amber Benson (who would go on to play Tara on Buffy the Vampire Slayer), calling her a c*nt and a “beeeyotch” and threatening to shove alternately his shoe and a bottle into her fave. Again: playing a character. But also: not the kind of character who fit in with the Romeo-then-Jack-Dawson trajectory of Leo’s career. There’s a later scene in the movie where Leo’s character calls Jenny Lewis’ character a whore for not having sex with him. It’s honestly incredibly exciting work from the young actor. The question of how much of himself Leo was bringing to the role is unanswerable, but the idea that he was improvising these scenes with his buddies gives the whole film a kind of Stanford Prison Experiment meta-vibe. It makes for a fascinating film in that respect.
This part where Leo picks his nose while wearing gross fake teeth. It’s tough to imagine this one being on his Cecil B. DeMille Award clip reel, you know?

The part where Leo’s character asks, “Do you guys like bathe every day and wash yourselves with soap?” Not just because it conjures the image of a gross and stinky Leo trying to mack on Jenny Lewis (though it does), but because it’s indicative of the places these scenes go when they start to lull. There are scenes where the misogyny and sexual identity politics give the film an electric charge, but aside from a strange interlude when Connolly leaves the booth to go try and score a movie role from a horny female producer, there isn’t much that happens in this movie. The ’90s were the era for talky diner indies, but “do you wash yourselves with soap?” does feel like the nadir of something.
The jazz. Oh man. It doesn’t have anything to do with Leo, and it’s mostly confined to the beginning of the film, but the first 15 minutes are rife with an acid-jazz burlesque taking place while Tobey Maguire goes on an unsuccessful date. Jazz and Tobey Maguire: two great (?) tastes that taste great (???) together.
The part where Leo makes this face.

Honestly? Most actors have five WAY more shameful things about their worst movies. Having seen the movie, it’s kind of mystifying that DiCaprio and Maguire have spent the better part of 15 years keeping Don’s Plum buried. It’s self-indulgent, prurient, immature, and obnoxious. We’ve all already accepted that this was Leo’s persona in the ’90s anyway. Nothing in this movie is enough to take Leo down, even a little. Keeping the film bottled up is what’s making him look petty.