And if you're gonna mention Jonn Hodgman (more recently famous for being the PC guy in the "I'm a PC.. and I'm a Mac" commercials), you must mention his good buddy Jonathan Coulton
, who's like the love child of Tom Lehrer and Fountains of Wayne. Really great, listenably silly music on topics as far-ranging as zombies, killer robots, evil geniuses, and suburban malaise. Wonderful, wonderful stuff!
Top five JC songs right off the top of my head:
1. Re: Your Brains
2. Code Monkey
3. Mandlebrot Set
4. Skullcrusher Mountain
5. and lastly, but not at all least(ly), his absolutely priceless cover of Baby Got Back