"This is TED telling BILL to SHUT UP!"

(repeat 27 times)

Fear of a Black Hat.

Add Grandma's Boy to that list and we're in business.

The funniest movie that no one has seen.

Agree with those who named Flirting With Disaster and Shakes the Clown.

Some I haven't seen mentioned:

Idiocracy (bc anything that Mike Judge touches turns to gold)
Slums of Beverly Hills
To Die For (probably underrated as a comedy bc of how dark it is, but it's still funny as hell and Nicole Kidman's best role ever)

...and I'll go ahead and just say any Christopher Guest movie bc I don't think he gets enough respect for how brilliant he is

I don't know...whenever I recommend Wet Hot American Summer to somebody, I am surprised by how many people tell me they actually have seen it. And it's been aired on Comedy Central more than a few times, so that helps. I think it's built up a good audience since it first came out.