Courtesy of jeffheikkinen

[bighairyviking]

Step 1: Put your MP3 player or whatever on random

Comments

[sun_in_her_hair]

2: primadonna from phantom of the opera
4: Weird Al: Alberqurkey (spelled wrong, but you get the idea)
6: GIR's doom song.
20: Hallelujah (spelled wrong), written by leonard coehen and sung by rufus wrainright

[darkly_cute]

19, New Math by Tom Lehrer
23, I'm Gonna Sue, Weird Al

[lenora_rose]

9: The Beatles - Taxman
22: Stan Rogers - The Mary Ellen Carter
25: Peter Gabriel - Solsbury Hill

21: Rush. Dammit, I don't recall the song.

And I'd have missed the Rufus Wainwright part of Hallelujah, since I have versions by Leonard Cohen himself, and Jeff Buckley, and have heard John Cale, Rufus Wainwright and Bono cover it. And not all the above have that exact lyiric(Leonard Cohen's second version, for instance, lacks it.)

[lenora_rose]

Rush, Tom Sawyer!

[ardeth_bey]

8) Here I Stand Before Me - Crash Test Dummies (I have the CD)

10)Ode to a Superhero - Weird Al Yankovic

17)Living with a Hernia - Weird Al Yankovic

The others that I know for sure, other people have already guessed.

[jeffheikkinen]

Lenora nailed the ones I'd have gotten easily, but a couple of the others are tickling something.