Much more subtle, but anyone for The Men Who Stare At Goats?
Perfect cast and so **** funny because you have no idea if it's a joke or not.
Along those lines I'd add Fargo and American Psycho... both hilarious if you watch them enough.
You're talking about the one where he was doing like 600 whippets a day? That was ****ed up ****.
But dude is somehow alive, sober and well. Shockingly.