I put iTunes on Party Shuffle, and these are the first ten songs that came up.

1. Hithhiker's Guide to the Galaxy, Episode 9 - Douglas Adams
2. Women and Men - They Might Be Giants
3. Not Even Jail - Interpol
4. Awake My Soul - Derek Webb
5. Arc of Time(Timecode) - Bright Eyes
6. Beautiful People - Rusted Root
7. Love My Way - The Psychedelic Furs
8. Steve Wozniak, Part 2 - IT Conversations
9. Clementine - Elliot Smith
10. Extra Savoir-Faire - They Might Be Giants

(idea from Brendoman)