Dr. Strangelove. The cast is absolutely incredible, the humor is just dark, and it reminds me of high school (I graduated from a high school that was featured in National Geographic because our school symbol is a mushroom cloud.)
Labyrinth. Excellent cast, masterful puppets, awesome music- I consider the song "Hallucination" off the soundtrack to be one of the best instrumental pieces out there. Have seen Bowie live which makes it that much better.
Akira. The bike....need I say more?
The Producers- original Zero Mostel and Gene Wilder version. Can't think of many films where someone goes into hysterics to the point that he literally turns red due to a rise in blood pressure. Just one of the reasons it won Best Picture the year it was released.
Event Horizon. Okay, it could have been much better, but then again a lot of that movie got left on the cutting room floor as the studio, and the test audience, thought the uncut was far too disturbing. Also contains one of my all time favorite lines in film- "Hell is just a word. The reality is much, much worse." That line makes me really happy. (Yes, I'm on medication, don't worry about it.) Sadly, there is no known copy of the original version of the film- which pisses me off to no end.
You could throw any of those on and I would be quite content. Unfortunately, can't watch a couple of them with my son, as I think the whole gut dropping sequence in Akira, or the dead wife in Event Horizon, would probably do too much damage.
Yep, I have way too much time on my hands in a small town.