Fun if similar to the movie Death of Stalin and the example of such a vacuum. No spoilers but Stalin isn’t the only one who dies. Great comedy. Highly recommend.

Wayne’s world is almost too on the nose honestly. Myers & co captured the 80s rocker character well. They/we were everywhere then. But it’s a silly movie so doesn’t quite fit with your theme.

My original thought was Fast Times. Just searched quintessential gen x movies and it came up on top of the list along with all the others mentioned here. Oddly I haven’t seen half of them lol

Xer here. Not sure about clerks tbh. It came out rather late plus I fell asleep watching it lol. Would suggest repo man instead (until I think of something more suitable ).