Down with Love was on HBO one night in my sophomore year in high school.
A friend of mine started watching it as a joke.
We finished it.
It rules.

I do not have a problem with "offensive" jokes.
It just sucks when they turn out not to be funny (for example: Tropic Thunder).

Burn After Reading
The "axe to the skull" shot was just really cool.
and so was the movie.

Night at the Roxbury
I do not know what to tell you if you do not like this movie.
Perhaps: "oh man, I wish you liked it"

The works of Christopher Guest win all contests of awesomeness.

"haha"
"good one"

The Life Aquatic with Steve Zissou
It is awesome, cool, and hilarious. And great and crazy.