Janet asked about the best satire songs.
Let's just admit that Wierd Al is the best at doing this on a pop culture level. He just is. Every couple years he comes out with an album and he's got at least one or two songs on it that are stellar satire and damn funny. I'll Be Mellow when I'm Dead, Yoda, I Lost on Jeapordy, Eat It, Smells Like Nirvana, Jurrasic Park, Amish Paridise, White & Nerdy- I could go on forever. Some of the videos are pure gold, too.
Others who list will hit the other highlights, but there's three who got life on the internet that I must include:
The Ultimate Showdown of Ultimate Destiny
Stick Magnetic Ribbons on Your SUV
This Land (Jib-Jab)