As far as sneakers goes, you arent the only one. One day Ill have the presence of mind to toss a tape in the machine while its on.
Most of the movies I would add to the list have already been mentioned. Its nice to find out that I havent just been picking wierd movies, that there are others out there who enjoy them as well. (Ask my wife. She's sat through plenty of strange and bizarre movies, not saying a word, because she knows how much fun I'm having.)
I dont know if these fit the bill as far as obscurity goes, but around here (i.e. my hometown) not many have heard of them:
Toys
Brazil
I'd say any godzilla movie (except for that matthew broderik thing), but I think Id just be preaching to the choir here.
The Adventures of Baron Munchausen
The Puppet Masters (about the aliens, not the deranged puppets)
Aw heck, just about anything Gilliam works on turns out pretty good.
And no one has mentioned Death Race 2000? A great campy flick with Stallone and Carradine, cars, blood, death, and destruction?
And lastly, how about Rollerball? (The older one, though the newer one was watchable at least.)