This is for a Rhode trip to Cincinnati. I tried to branch out on this one a little bit more in terms of artists. I haven’t given it a test drive yet, but I’m sure someone will give me feedback on it.
1. Start Wearing Purple (Gogol Bordello)
2. The Purple People Eater (Sheb Wooley)
3. Inflammatory Writ (Joanna Newsom)
4. Stone Cold Dead In The Market (Ella Fitzgerald and Louis Jordan)
5. Old Car Blues (Paul Kotheimer)
6. Are You Gonna Be My Girl (Jet)
7. Moon Over The Freeway (The Ditty Bops)
8. A Summer Song (Chad & Jeremy)
9. Kaze Wo Atsumete (Happy End)
10. Prelude in E Major [WTC Book I] (Glenn Gould/J.S. Bach)
11. Fugue in E Major [WTC Book I] (Glenn Gould/J.S. Back)
12. Azerbaijan Love Song (Dawn Upshaw/Luciano Berio)
13. Tank! (Yoko Kanno)
14. Qui Veut (Ol’Kainry)
15. Dancing In The Street (David Bowie and Mick Jagger)
16. Saturday Night Fish Fry (Buddy Guy)
17. She Caught The Katy (The Blues Brothers)
18. Misty Mountain Hop (Led Zeppelin)
19. I Walk The Line (Johnny Cash)
20. I’ll Follow The Sun (Don Byron/The Beatles)
An Ergodic Walk 
I’m going to trust you, but I’m not sure that I’ve ever enjoyed a song sung by someone named Yoko…
Also… Cincinnati and Zeppelin. Because it wouldn’t be a comment from me if I didn’t correct your spelling. :-p