I'm still working on my 20xx list, but I can contribute a few ideas to the California playlist concept. I couldn't find videos for all of them:

1. California Stars by Wilco



2. California Dreamline by Rheostatics




3. Goodnight California by Kathleen Edwards



4. California by Low



5. Not California by Hem



6. California by Josh Ritter



7. Come a Long Way by Michelle Shocked



8. Losing California by Sloan



9. I Remember California by REM

10. San Andreas Fault by Nathalie Marchant