Filmed in 1996 and given a very limited European release in 2001, Don’s Plum is a micro-budget indie film.  It’s about a group of young friends who meet up at a diner called Don’s Plum and spend the entire night talking to each other.  It’s filmed in grainy black-and-white and the majority of the dialogue is improvised.  The main characters continually let us know that they’re friends by referring to each other as “bro.”  There’s a lot of conversations but none of it adds up to much.  In many ways, it feels typical of the type of indie films that were inspired by the early work of Richard Linklater and Kevin Smith.  Unfortunately, it’s not a particularly good or interesting film.

That said, Don’s Plum has achieved a certainly level of infamy due to the fact that two of the talkative friends are played by Leonardo DiCaprio and Tobey Maguire.  DiCaprio plays Derek, an arrogant, abrasive, and manipulative womanizer.  Tobey Magurie plays Ian, a weirdo with a spacey smile.  DiCaprio and Maguire were both up-and-coming stars when they filmed Don’s Plum.  DiCaprio, who had already received his first Oscar nomination and who had just finished shooting William Shakespeare’s Romeo and Juliet, was a year away from Titanic.  Maguire was also a year away from his breakthrough role in The Ice Storm.  DiCaprio and Maguire not only starred in Don’s Plum but they’re also responsible for the film having never been commercially released in North America.

There’s a lot of conflicting stories about why DiCaprio and Maguire have both attempted to keep the film from being released.  DiCaprio’s story is that neither he nor Maguire were aware that they were shooting a feature film.  Instead, they thought they were making a short film and the only reason that they even showed up during the two nights of filming was because they were friends with the director, R.D. Robb.  The film’s producers, on the other hand, claimed that DiCaprio and Maguire always knew that they were making a feature film and that the reason they objected to the film’s release was because they were embarrassed by how much personal information they revealed while improving.  The truth is probably somewhere in between.

Of course, it’s also possible that DiCaprio and Maguire didn’t want the film to be seen because the film kind of sucks.  The dialogue is tedious, the film’s pace is painfully slow, the grainy black-and-white cinematography is dull, and the film’s soundtrack is so muddy that it’s difficult to understand what the characters are actually talking about.  Playing a total douchebag, DiCaprio does get to show off his natural charisma but Tobey Maguire appears to be dazed and confused in the role of Ian.  To be honest, both DiCaprio and Magurie are outacted by Kevin Connolly, who plays one of their friends and who would later go on to play the only vaguely likable character on Entourage.  (Connolly also directed the Brechtian gangster movie, Gotti.)  Connolly may not be as showy as DiCaprio or Maguire but his steady presence provides a nice contrast to Maguire’s fidgety mannerisms and DiCaprio’s need to always be the center of attention.

DiCaprio, Maguire, and Connolly are joined by Scott Bloom, playing the boring friend who will sleep with anyone.  Jenny Lewis gives a good performance in the role of DiCaprio’s quasi-girlfriend.  Amber Benson plays a hitchhiker who is abruptly chased out of the diner (and the movie) by an incredibly obnoxious DiCaprio.  At one point, Ethan Suplee wanders through the diner, playing a character who is identified in the credits as being “Big Bum.”  Everyone gets their chance to improv a monologue, often while staring at the bathroom mirror.  Eventually, DiCaprio’s character reveals a tragic secret from his past and it would have been an effective scene if not for the fact that it comes out of nowhere.

Oh, improv.  Improv has led so many directors and performers down the wrong path.  It’s an attractive idea, I suppose.  Get a camera.  Get some of your best friends to visit for the weekend.  Shoot a movie!  Who needs a script when you can just make it up as you go along.  Unfortunately, what’s often forgotten is that improv only works if you have a solid story idea or theme that you can continually return to if and when the improv itself starts to lose focus.  Curb Your Enthusiasm is a famous for being improved but all of the improvisations are based on a plot that’s discussed and set in stone ahead of time.  Don’s Plum feels more like one of those weird shows that George Clooney and Steven Soderbergh came up with for HBO in the mid-aughts.  (Remember that one with the acting class?  Frank Langella played a pompous acting teacher named Goddard Fulton and one of his students got a role on One Tree Hill.)  Don’s Plum meanders without any real direction, with none of the actors really trying to challenge each other.  An improved film like this needs a force of chaos, like Rip Torn provided for Norman Mailer’s Maidstone.  Instead, this film can only offer DiCaprio caricaturing his pre-Aviator persona as a hard-partying and often abrasive movie star.  (If nothing else, this film shows just how much DiCaprio has benefitted, as both an actor and a public personality, from collaborating with Scorsese.)

Don’s Plum is one of those films that is only well-known because of how difficult it is to see it.  But now you can see it on YouTube!  You can watch it and then you can ask yourself what all the controversy was about.  At this point, I think both DiCaprio and Maguire have proven themselves as actors and allowing for Don’s Plum to get, at the very least, a proper video release wouldn’t hurt the reputation of either one of them.  If anything, the best way to get people to forget about Don’s Plum would be to give them to the chance to try to sit through it.  There’s nothing about this film that sticks with the viewer, beyond the fact that neither Leo nor Tobey want anyone to watch it.