4273 songs, 11.4 days.
Sort by song title; first and last?
First: '85 Radio Special by They Might Be Giants -- it's a little B-side from their first compilation album.
Last: It has Japanese character for a title, so I can't reproduce it. It translates to "Simple and Clean" and is from the "Kingdom Hearts" soundtrack. I guess that means I'm admitting my fascination with video game music.
Sort by time; first and last?
First: Fingertips (11) by They Might Be Giants (0:04).
Last: Dies Irae from the Verdi Requiem, by the Robert Shaw Chorale (36:41). My chorus is singing this piece right now and it's awesome (in both senses of the word).
Sort by album; first and last?
(Not counting items with no album name.)
First: So Far Away, by Staind (from "14 Shades of Gray")
Last: Numb, by U2 (from "Zooropa", of course)
Top five played songs?
Naturally, these are songs that I tend to go back and listen to again as soon as they play the first time. They are:
Aluminum, Barenaked Ladies, from "Everything Acoustic"
Next Time, Barenaked Ladies, from "Everything to Everyone"
'97 Bonnie and Clyde, Tori Amos, from "Strange Little Girls"
Side, Travis, from "The Invisible Band"
Aluminum, Barenaked Ladies, from "Everything to Everyone" (tied with two other songs)
You might conclude from this that "Aluminum" is my very favorite song. You would not be too far off.
Find "sex"; how many songs show up?
Three. Wild Sex in the Working Class by Oingo Boingo, So Unsexy by Alanis Morissette, and Sexy Sadie by the Beatles.
Find "death"; how many songs show up?
27 songs, but only because it matches the Dead Milkmen album "Death Rides a Pale Cow". Not counting these song, there are four: Judas' Death from "Jesus Christ Superstar" (original London cast album), Starve to Death by Chris Whitley from the "So I Married an Axe Murderer" soundtrack, "Death's Door" by Depeche Mode, and "Deathwish" by the Police.
Find "love"; how many songs show up?
171 songs. Again, this matches artist names (Laura Love, Lyle Lovett) and several album names as well.