Adult Swims programming from the exact same time you mentioned helped shape me into who I am now, lmao. What an awesome time for TV. I can remember sneaking downstairs to the TV to put on Space Ghost Coast to Coast. I didn't "get it" but I was very aware that I liked that type of dry humor.
Mulholland Drive.
Trust me on this...just put all technology away when you watch this and give it your 100% attention. One of the craziest movies I've ever seen.