We can't be direct, so we end up saying the weirdest things.

My Dinner with Andre (1981)

Chosen by the teevee show Community (kinda, it inspired me to watch it anyway). Here's what the avclub.com's review of the episode had to say about the film: 'it sounded like exactly the kind of pretentious bullshit I would enjoy at the time. (It was, but it’s a good film and well worth seeking out.)'

My favourite show currently on the air is Community - a brilliantly funny and often touching examination of friendship and pop culture. One episode decided to do a riff on the odd dinner talk movie My Dinner with Andre, a film that I had been meaning to watch for years as I'm a big fan of Wallace Shawn.
As a big Shawn fan it's hard not to be slightly disappointed in the first half as it's not so much a conversation as a monologue delivered by Andre Gregory but Shawn becomes more forceful as the evening wears on (it's not quite in real time as I believe there is a longer cut) and is obviously a constant presence.
The talk is indeed pretentious and doesn't really offer much in the way of insight but that's part of the films easy going charm.
There is a pleasing rhythm that keeps the film afloat and never boring.
Oh and the Community episode is now ten times as funny in hindsight.