Ok, fine:

Total volume of music on my PC:
11.72 GB, which includes approx. 1 GB of podcasted material

Last CDs simultaneously purchased (for myself):
Tenacious D - Tenacious D
Jack Johnson - In Between Dreams

Last song purchased at iTunes (with gift card - You didn't think I'd spend my own money on DRM'ed music, did you?):
Such Great Heights - The Postal Service

Song playing right now:
Speak, See, Remember - Pavement

Five songs/CDs I listen to alot - This will be hard as I don't really do a lot of repeat listening these days:
1. There's Nothing Wrong With Love - Built to Spill
2. The Band - The Band
3. Waiting for Columbus - Little Feat
4. The Harder They Come soundtrack (or the Tougher Than Tough box set)
5. American Water - Silver Jews
6. (Sorry, couldn't leave this off) Hunky Dory - David Bowie

Five songs that mean a lot to me - I offer no explanations and could easily have picked twenty others:
1. (Don't Go Back to) Rockville - R.E.M.
2. Taste - Phish
3. Broken Arrow - Robbie Robertson
4. Brooklyn (Owes the Charmer Under Me) - Steely Dan
5. Into the Mystic - Van Morrison

First concert:
Either Kenny Loggins (with my summer camp) or Air Supply (with my parents) - not sure which came first.

First concert by choice:
Steve Miller Band

I know I'm supposed to tag three people at this point, but everyone I know has already done it, so I'm gonna let it die here. If you're dying to share, just do it already.

Oh, my apologies for the lack of audio lovin'. I'm just tired and don't have much to comment on at the moment. I haven't forgotten about you.