Agreed. There are many that are definitely generational. I think Office Space transcends well. When it came out I was probably 10, I didn’t have an office job until I was in my late 20s. It was sort of funny when I saw it as an adult, but after working in a cube farm for the first time I saw it in an entirely new light. Rolling Kansas is a good one too. Just a weird-ass, slow paced comedy about some potheads looking for their parent’s long lost pot farm and running into Rip Torn along the way lol