1. Snoop Dogg
Let's start this off with a bang shall we? (And oh, by the way, every single one of these takes is offensive in some way/ multiple ways. You have been warned). I always heard that Snoop Dogg was no talent. The naysayers are wrong. Yes, he's offensive in every single way - violence, sex, misogyny, etc. But he has got such a smooth flow, much better than Dr. Dre's. Everyone knows Gin and Juice, but Take it Back to '85 is much more fun: Make sure you're wearing headphones. His best music was made when still producing music with Warren G (beautiful jazzy voice) and the rest of Death Row records. Yes, rap is music. Deal with it.
I don't like his raps ironically. No, I sincerely like the early songs like The Real Slim Shady. Ask anybody in their mid-late twenties, and unless they're lying, they like it too. They'll bluff and beat around the bush and try to be all ironic, but don't be fooled. If it were to come on the radio and they were alone in the car, they'd start rapping it too, badly, with hand motions. Here are the lyrics, and they're clever.
3. Albert "Bert" "The Machine" Kreischer
My husband and I are big fans of stand up, and Albert Kreischer is possibly our favorite for live shows. He has a great stage presence and is able to improv like a pro - the sign of real stand up. While we were at a show in Baltimore in the summer, a group of rather trashy ladies were heckling, whooping, just being plain obnoxious, but he dealt with it with pizazz without becoming too crazy or having to throw them out. He started the show by throwing off his shirt and pouring whiskey all over himself; it was fantastic. What can I say, I like low-brow entertainment. (My moonshine making ancestors would be so proud.) His most famous sketch (which is actually fairly clean) concerns his escapades as a college study abroad student in 1990s Russia, and how he got mixed up with the Russian mafia. NOTE: I just listened to it again, and no, it is not clean. Not even a little bit.
4. Dave Chappelle
Some people think he's racist. They are patently wrong. He is clever, and he is signifyin'. I really wish I'd been here to see his show in D.C., his hometown. There are so many good clips of his that it was really hard to pick, but here are some of my favorites.
5. The Rocky Horror Picture Show
And with that, I just lost whatever audience I once had. Full speed ahead! If you don't know what I'm talking about, you really should be familiar with the pop culture reference Time Warp. "It's just a turn to the left...." Actually, I have no right to list this at all, since I've never been to a live showing and am therefore still a virgin. But I have such good memories of watching this on a tiny TV with my college friends and dancing the time warp. This is seriously the most offensive thing on this list though: it has the song "Sweet Transvestite" and ends in an orgy. It's also very clever though - a great riff on the 1950s drive in sci-fi movies.
6. Eddy Izzard
Speaking of transvestites (I don't get to use that phrase much...). Eddy Izzard is a cross-dressing British stand-up comedian with a great delivery and hilarious jokes. This is my favorite version of the American vs. British culture pieces.
7. South Park
This show is popular for a reason: it's the best satire on the market. And what's even better is that it bucks the trend of riffing only on conservatives: primarily it destroys liberal sacred cows. In that attribute, it's virtually alone amongst TV shows. This was the only show with the nerve to say that Americans love Walmart because of greed, not that Walmart was some monster by virtue of existence. They even had the audacity to attack the hypocrisy of obese anti-smoking advocates, which is unthinkable today. They can show subtle balance though too: the brilliant post 2008-election episode called "About Last Night" (which was in fact produced that night) hit the nail on the head regarding fans of both parties. As for the actual candidates, well, I won't give it away.
Y'all, they even mocked Muhammad in the brilliant two-part saga Cartoon Wars (which the creators discuss here). It's like they have a death wish or something. Comedy Central refused to allow them to include an image of Muhammad just standing there, and the episode ends with a supposed creation of terrorists mocking America, Jesus, and the flag with feces. The irony is golden: look what we're allowed to put about America and Christianity. Seriously, nobody talks this way; how do they get away with it?