I think the only comedy movie I have watched again and again and still could sit through today is Caddyshack. So that is my number one!
I must see Tropic Thunder again though, that was hilarious! The funny thing is...a bunch of friends (all people of color) were talking about blackface years ago and we made up our minds that it's always racist, ALWAYS. In US culture it's so loaded that you just can't do it without it being racist. Well, I don't know now! Robert Downey Jrs part wasn't making fun of black people so much as it was making fun of RDJ's character. They may have pulled off the one way that it can be done.
Team America World Police. I took my kids to this with reservations, I kept thinking this might be a bad idea. They were 13 and 11 at the time, and I thought, how bad can puppets be? Then...puppet sex! I was dying...of laughter! Even now, when something typical American stupidity happens (you know, reality tv type stuff) we look at each other and sing, "America! F*ck yeah!"
Deuce Bigelow Male Gigolo. I laughed until my stomach hurt and I was howling.
Super Troopers. Our kitten is even named after our favorite scene, "Evil shenanigans!"
I just noticed that all my favorites are totally nonsensical and ridiculous. That is my type of humor, I guess! lol