Ten random songs about ten random people?
Not too random.

1. Styrofoam Plates - Death Cab for Cutie
2. Losing My Mind - Stephen Sonheim
3. I'll Stand By You - The Pretenders
4. Children Will Listen - Stephen Sondheim
5. Two Headed Boy - Neutral Milk Hotel
6. Gravity - Sara Bareilles
7. Finishing the Hat - Stephen Sondheim
8. I'll Be Seeing You - Bing Crosby/Billie Holiday/Frank Sinatra (Pick a version.)
9. Riches and Wonders - The Mountain Goats
10. Caberet - Frank Ebb & John Kander