Grr. I could tell you where many of these come from but not the exact song...

1: Santa Esmerelda, "Don't Let Me Be Misunderstood"
2: Clearly Johnny Cash something
3: Pacific Overtures, "Poems"
4: Jet, "Cold Hard Bitch"? Or is it their other one?
10: Barenaked Ladies, "Postcards"?
11: Kiss of the Spider Woman, "Kiss of the Spider Woman"
16: Nightmare Before Christmas, is the song itself called "Something's Up With Jack"?
17: I feel like this is Fountains of Wayne...
17: Ragtime, "Atlantic City"
19: A Little Night Music, "Miller's Son" (pin my hat on a nice piece of property...I could have gotten this one without the title being in the first line, thank you)
20: Chicago, "Cell Block Tango"
21: Flogging Molly, "Every Dog Has Its Day"?
25: Flogging Molly, "Black Friday Rule" (very hard to get after mine, I know...)
26: I think this is Indigo Girls? "Galileo," is it called?
27: "Respect," but I have no idea who sings it.
28: "In the Jailhouse Now," I don't know who sings it but it's from O Brother Where Art Thou?
30: Utena, closing theme, but damned if I know what it's called