I remember one day hearing my father downstairs laughing his ass off. Went down to see what was so funny to find he had just discovered Mystery Science Theater 3000, and was losing it watching The Giant Gila Monster. I sat down to watch. I didn’t really get it then, but I’ve been a fan ever since.
Teenagers From Outer Space is a good start. It was hilarious to me when the old man was muttering and singing “it’s the New Zoo Revue” and he looked like the man from the show. I had actually seen the show (don’t blame me, we didn’t have cable and after you watched cartoons, it came on) It was just so obscure :D