88 Minutes is hilariously bad, definitely a good watch.
Any "How Did This Get Made?" listeners here? A hilarious podcast about making fun of bad movies. After getting into that and watching a lot of the movies, I'll throw up Gooby, a weird kids movie that was hilariously bad, and Tiptoes which stars Matthew McConoughey and Gary Oldman as twin brothers, but Oldman happens to be a little person.
I used to work in a video store in my college years and would seek out the bad movie gems, if you can find "Boa vs Python" for a night with some beers and some buds, its fantastically bad like The Room. So many awful lines, plot lines that make no sense, and classic B movie stuff like a young couple about to screw in a parked car in the woods. Giant snake eats the guy who is about to go down on a girl, and then the snake starts going down on the girl who is of course delighted until she's eaten alive. A news reporter is trying to call someone on his cell phone and can't get a signal and says to himself "jesus, what am I paying these people $240 a month for!?", a woman with a giant snake tattoo on her back gets angry at her boyfriend for pranking her with a fake snake: "come on, you know I hate snakes!!"