I heard about this movie several months ago, and I've been trying to track it down to give it a watch, and now it appears that it IS out on DVD, which is awesome. I should be able to find it with to much difficulty. I'm totally new to the genre (with the exception of Broke Back Mountain) but I was wondering if anybody knows of any other movies like this one for me to check out while I'm exploring the genre. Thanks in advance!
The greatest trick the Devil ever played was the one with deck of cards and...
Do you mean, like, road movies, or movies that explore homosexual relationships, or just movies with a similar tone/atmosphere?
....eh, check out some Jon Moritsugu (similar director, a bit more extreme in some aspects but also a bit more openly comical), Jon Jost (who does a lot of interesting "road movies" and experimental independent features; truly one of the great directors of our time), some Gus Vant Sant, and some Godard (especially Pierrot Le Fou).
I agree with your recommendation of Gus Van Sant. I'd particularly point to Mala Noche and My Own Private Idaho. Both are love stories involving hustlers that came out just a little before The Living End. Mala Noche is also a shoestring-budget film. The big differences are that neither deal explicitly with AIDS and that neither film appears to be directly inspired by the political climate of the Reagan/Bush years.
I might also recommend Frisk from a few years later. It has the same unpolished edginess in its treatment of hustlers, but the subject is much more extreme--gruesome, fetishized murders . . . sometimes of teenage boys.
For early films dealing with AIDS, check out Parting Glances and Longtime Companion.