Watched this one recently with my partner. Strange, disturbing, and surprisingly good. Wil Wheaton is great in it.
Rent-A-Pal
Another truly unusual film. Quite a few films by Shinya Tsukamoto would qualify here.
Tetsuo The Iron Man
A couple films by Vincenzo Natali deserve to be on this list as well - the science fiction labyrinth drama Cube and the surreal thought experiment Nothing. (Note that Cube has a few sequels, but not by the same team and not really worth your time in my opinion.)
Cube
Nothing
I like this one.
I guess “Dark City” might count or is it too high budget?
That’s one I really want to like but I can’t watch it because the cut/cut/cut/cut rhythm makes me feel like I’m having a stroke.
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I just watched Things for the first time tonight. It’s a straight-to-video release that was shot on VHS. It’s not a good movie, nor is it well made, but it’s so incredibly strange that it’s worth a watch simply as a curiosity.
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It’s on “Shudder” currently available standalone or (recommended) as part of “Joe Bob’s Last Drive-In”.
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The kindest thing I can say about Things is that it exists.
Okay, the line “This will be crunchy in his tummy” is hilariously ridiculous, fine, but I have to draw the line there.
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I experienced it as part of Joe Bob’s Last Drive-In… I just signed up for Shudder, so I’m going through all of the episodes now. I grew up on MonsterVision, which is where my love of B-movies began, so Joe Bob is probably the reason why I love MST3K so much.
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Just rewatched the original Rollerball yesterday, still a good film. It has enough of that period’s verite style to remain interesting rather than feel completely dated.
A fun cheesy film is Damnation Alley. Based on the novel by Roger Zelazny, and with an iconic vehicle, the Landmaster.
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A friend loaned me the novel of Damnation Alley about a year before the movie was released. We eagerly awaited the movie which proved to be a mistake.
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It stars Jan-Michael Vincent and George Peppard. That right there puts an upper limit on how good it can be. 
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Damnation Alley is one of my favorite cheesy movies! I had a VHS copy for a long time and was happy when they finally put out a DVD version. This is also my go-to example when people complain about how they always remake good movies and not conceptually good movies that could have been better. This could be a great effects-heavy post-apocalypse popcorn movie with a big action star like The Rock in a leading role. For now, I’ll just rewatch the original. 
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This is a great thread and I’m either enthusiastically agreeing with posts for movies I’ve seen or jotting down to-watch lists for moves I haven’t…
But my contribution here is – seriously, you guys, this is not a movie that I think would work for MST3K nor is it a movie anyone should ever watch, ever. I mean, I watched it. But I watch all kinds of things no one should watch.
It’s called After Last Season. Take a look at this AV Club article on it by Ignatiy Vishnevetsky: The Last Year At Marienbad of Z-grade bad movies
If you absolutely must, it’s findable on YouTube (sometimes – it comes and goes). I’ve seen it in its entirely twice, though I’m not sure I was fully conscious through all of it. I don’t recommend watching someone’s comments on it or some hapless attempt to riff it. It should either be seen exactly as it was made, or (the much saner option) – never seen at all.
Oh, poopie – I thought I’d checked before posting, but @Guiron you had already noted ALS. I commend you – excellent suggestion. 
Some of you may be familiar with Rock n Roll Nightmare (Rifftraxx gave it the business), but if you really want a bad cheesy movie try its sequel…
Intercessor: Another Rock n Roll Nightmare
Here’s a bit of it…
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I didn’t watch much of his MonsterVision stuff 'cause I haaaaate commercials. But what I did see was brilliant. The Warriors and Back To The Future 2 are just brilliant.
I started watching Joe Bob on The Movie Channel. Talk about the Salad Days. All the scream queens and action guys and scream queens and movie producers and scream queens…
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Joe Bob’s Last Drive-In is all sorts of brilliant. Justifies a Shudder subscription singlehandedly.
We simply had too much when we had Joe Bob’s MonsterVision, USA Up All Night, and MST3K all running live once upon a time.
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And “Night Flight” and Elvira!
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I am so submitting that to the Smithee Awards people… (o.O)
Especially since Rock 'n Roll Nightmare won Worst Picture and Stupidest Looking Monster in 2014, won Stupidest-Looking Monster again at the MegaMeta Smithees against all the other Smithee winners in that category from 2012-2016… and then won the category at the UltraMegaMeta Smithees against the other four MegaMeta from 1992-2016.
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