I've never seen the movie, but I did get to know David Stutman (the Producer) and I can personally see why he sued Leo DiCaprio and all of his agents for basically stopping the movie from distribution and thereby stopping a lot of people from getting paid.
Stutman and some of the others in the producer/writer/actor group were very close friends - there was a lot of smoking pot, drinking, and sexual conduct (not limited to heterosexuality, and involving two big name actors, if you catch my drift). The movie, while seen as a very endearing art-house-style flick by the actors, suddenly became dangerous when Dicaprio was in pre-production for Titanic and Toby was being slated for Cider House rules. With Titanic being released that year and Cider House a year or so later, Don's Plum basically amounted to an early heavily contrasted look at the two actors that the public should never take. Leo's agent's filed an injunction that Stutman had illegally created a movie that Hollywood lawyers had not been present to administer signing of.
Long story short, Stutman made a movie that was distributed 5 years later to the back of the VHS/DVD bin, when it might have been a hit if it was sold or even screened simultaneously with Titanic. I believe that the studio settled with him and forced him to put it off 5 years. I still remember Stutman well, with his tiny house in the middle of Venice Beach, with two big dalmations and a slew of precious Disney cels.
