South Park: Hell on Earth 2006
Biggie Smalls: You got to get me to Los Angeles!
Butters: Can't you just take a plane?
Biggie Smalls: How, punk? We don't use money in hell, nigga!
Butters: Well damn, nigger, there's gotta be some way!
This was a great episode, though I would have preferred a much more vicious attack on the spoiled teenagers from such shows as My Super Sweet Sixteen, a program I've seen about .5 seconds of, which was long enough to make me want to find the closest spoiled teenager and inject Windex directly into their eyeballs. I loved the idea of Satan behaving just like one of those spoiled brats and then realizing in the end that, even if he is the Devil, at least he's not as bad as those teenage girls.
Actually, I take back what I said about the episode not being vicious enough. This was what I would call one of those "fun" South Park episodes where lots of insane stuff happens and none of it really means anything. I loved the "Three Murderers" segments with Ted Bundy, John Wayne Gacy and Jeffrey Dahmer as ultra-violent versions of The Three Stooges, and dead rapper Biggie Smalls being summoned whenever someone said his name into the mirror three times.
As far as the moment most guaranteed to offend somebody, somewhere, I think it's a toss up between the priests with naked boys on leashes, and Steve Irwin showing up at the costume party with a stingray hanging from his chest.