I am going with one that I have watched multiple times during my "youth". It was on the movie channels all the time between movies.. a filler, if you will.
It is called "Bob's Birthday". It is about a couple, and the husband, Bob, is coming home from work (he is a dentist), and he is supposed to get changed and go out for supper with his wife as it is his birthday. BUT. What he doesn't know is that all their friends are hiding around the living room to give him a surprise birthday party. He starts complaining about his life and their friends all while his wife is trying to usher him upstairs to put on some pants.
It is hilarious and awkward. And even as a child, I was always enthralled with it. And watched it every single time.
Huh. Apparently it won an Oscar. Awesome!
What is a short film that you enjoy??