1. Saddam Hussein
In the South Park universe, the Butcher of Baghdad is a whiny, high-pitched, flapping-headed homosexual with the dual passions of world domination and anal. After dying and being sent to hell, he starts up a gay relationship with Satan, Prince of Darkness, then tries to destroy the planet by initiating the Great American-Canadian war. After being killed (again), he is sent back to hell, only to find that Satan is now dating another man, Chris. Satan and Chris kill each other over and over again, ending up back in hell each time. Finally, Satan calls in a favor and gets God to take Saddam into heaven, spends the rest of his days listening to Mormon storytime and building nuclear warheads in a chocolate chip factory. Eventually, he sneaks back to earth and takes over the Canadian government, only to be found hiding in a spider hole and executed.
2. Paris Hilton
The opening scene of Paris Hilton's appearance in South Park (to market her Stupid Spoiled Whore Video Playset) has her dog Tinkerbell grabbing a gun and shooting herself in the head. Forced to find a new pet, Paris dresses Butters up like a bear, calls him Mr. Biggles, and tries to buy him from his parents for $250 million. Eventually, Paris ends up facing off against Mr. Slave in a Whore-Off, and while Paris shoves a pineapple into her vagina, Mr. Slave counters by taking off his pants shoving Paris up his anus.
3. Michael Jackson
You know what will happen when Michael Jack..., er, Martin Jefferson moves to South Park: he'll climb into bed with the boys, he'll dangle his son Blanket out the window, a racist cop will show up looking to frame a black man only to find out the man is white, etc. You know what else? It's still funny.
4. Jennifer Lopez (and Ben Affleck)
For Latino Heritage day, Cartman makes his hand into a puppet and calls it Jennifer Lopez. With his prize money, he records a music video and sends it to a record company, causing them to dump the real Jennifer Lopez. The real J-Lo shows up in a rage and threatens to beat up Cartman's hand, which she eventually does. In the meanwhile, Ben Affleck dumps J-Lo in favor of Cartman's hand, ending up naked in bed with Cartman's hand around his penis. The real J-Lo ends up working at a fast food taco restaurant.
5. Mel Gibson
After being thoroughly disappointed by The Passion of the Christ, Stan and Kenny go to Malibu to get their $18 back from Mel Gibson. It turns out that Gibson is a raving lunatic who wears nothing but underwear, has half his face painted blue, and constantly wants to be tortured. Once the boys take the money from his wallet and head home, Gibson follows them in a tanker trunk, shouting at them in Klingon, and once he arrives back in South Park, he defecates in Cartman's face.
Honorable Mention: Tom Cruise
In an Emmy-nominated episode, the Church of Scientology believes that Stan is the reincarnation of L. Ron Hubbard. Devotee Tom Cruise shows up, only to run and hide in the closet when Stan insults his acting. And they make that joke last an entire episode.
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