Be it iTunes, Winamp, or even Windows Media Player (barf), Set it to shuffle and hit play. Then hit the next button and record each song that pops up.
I can't make sure you don't "cheat" to look like you listen to "cool" music only, but try not to skip songs. If it comes up, add it.
1. Keep Em Seperated - The Offspring
2. Scrollin Thru My *****es - Afroman (haha I can't believe this came up)
3. Time - Timbaland
4. Hump De Bump - Red Hot Chili Peppers
5. Million Miles - Mirah
6. Over My Head - The Fray
7. You To The Izzo - Jay Z
8. The Reason - Hoobastank
9. Teenage Dope Fiend - Flickerstick
10. Sexyback Remix ft. Clipse - Justin Timberlake