Eccy-eccy ftang zuboing!
Open iTunes/iPod or Windows Media Player to answer the following. Go to your library. Answer, no matter how embarrasing it is.

How many songs? 4020

Sort by song title:
First Song: (') Ions - Tool
Last Song: Zombie Eaters - Faith No More

Sort by length:
Shortest: March Of The Fire Ants - Mastodon (Live) @ 0:03
Longest Song: MX/Damone - Deftones @ 37:18 (although most of that is a silent gap)

Sort by album:
first: 2005 Demos - Anæmic
last: Fragment - Untitled demo

Top Five Most Played Songs:
Can't actually answer this one as I don't use iTunes for playing music.

First song that comes up on Shuffle:
Midlife Crisis - Faith No More

How many songs come up when you search for "sex"?
11 (Nearly all from Botch's "Unifying Themes Of Sex And Death")

How many songs come up when you search for "death"?
264 (I have a lot of Carcass stuff, what can I say?)

How many songs come up when you search for "love"?
20

How many songs come up when you search for "you"?
161