jaina

Either I have very musically inclined friends, or I listen to distressingly popular music, but you all managed to guess every song on my list. The full list with titles and artists, including the first people to guess correctly, is

1. I have wandered far and wide / for something real something to die for anony-mouse
Vanessa Carlton, "Wanted"

2. We are ten years old / We are holding our breath underwater

schneck128
Garrison Starr, "Superhero"

3. Each time you’d pull down the driveway / I wasn’t sure when I would see you again

anirt
Indigo Girls, "Mystery"
(unfair bonus question: who's singing the version I have?)

schneck128
The Chorallaries of MIT, specifically annakben trying to sound like Irene

4. Joseph's luck was really out / his spirit and his fortune low

bluefaith
Joseph and the Amazing Techicolor Dreamcoat, "Go go go Joseph"

5. There's no one in town I know / You gave us someplace to go

thedan
Jimmy Eat World, "Hear You Me"
(repeat unfair bonus question here)

schneck128
The Chorallaries of MIT, specifically the amazing Dan Bates

6. The seaweed is always greener / in somebody else's lake

tristmasjedi
The Little Mermaid (Sebastian the Crab), "Under the Sea"

7. Everybody's got a water buffalo / yours is fast but mine is slow

jedijeffp
Veggie Tales (Larry the Cucumber), "The Water Buffalo Song"

8. Is it the wind / over my shoulder

portnoyslp
The Full Monty (musical), "You Walk With Me" (incidentally, sung by

carbon_scoring at my wedding-- not this version, though)

9. Oh me name's Able Rodgers / a share man am I

rhi_silverflame
Great Big Sea, "Wave Over Wave"

10. Down in Minneapolis it's eleven o'clock / one eye on the moon and my money in my sock

schneck128
Billies, "Wichita"

11. She's into superstitions / black cats and voodoo dolls

bluefaith
Ricky Martin, "Livin' La Vida Loca"

12. Oh won't you come along with me, love / come along with me

fenchurche
Great Big Sea, "The Jolly Butcher"

13. Another turning point / a fork stuck in the road

bluefaith
Green Day, "Time of Your Life"

14. It's been two weeks three days long / I'm all alone since you've been gone another anony-mouse (leave your names, mice!)
Justincase (featuring Michelle Branch), "Without You"

15. Got the data in this morning / seems this whole time I've been rash

thedan

thedan, "Rose-Colored Glasses"

16. It'll all click when the mortgage clears / all our fears will disappear

thedan
The Servant, "Cells" (aka "the music in the Sin City trailer")

17. I'm goin' out tonight / I'm feelin' all right / Gonna let it all hang out

kelbebop
Shania Twain, "Man! I Feel Like a Woman"

18. All the old paintings on the tombs / They do the sand dance don't you know

profsparky
The Bangles, "Walk Like an Egyptian"

19. He called us slobbering / Said we were mangy

kelbebop
The Lion King (musical), "Chow Down"

20. Oh, my love, my darling / I've hungered for your touch

sonata960
Righteous Brothers, "Unchained Melody"

21. When the train rolls by / I'm gonna be ready this time

rhi_silverflame
Dixie Chicks, "Ready to Run"

22. Why are there so many songs about rainbows / and what's on the other side

bluefaith
Kermit the Frog, "The Rainbow Connection"

23. Have you heard the story of / a girl named Beth now known as Tex

sirrogue
Trocadero, "A Girl Named Tex" (from Red vs. Blue)

24. Miren el pepino / Watch the cucumber

jedijeffp
Veggie Tales (Larry the Cucumber and Bob the Tomato), "Dance of the Cucumber"

25. He robbed from the rich and he gave to the poor / stood up to the man and he gave 'em whatfor

portnoyslp
Adam Baldwin, "The Hero of Canton" (Firefly DVD Easter egg)