A 2009 iTunes Inventory

Number of Songs: 6215
Number of Albums: 1358
Most Recently Played Song: "Everything is One Big Christmas Tree" Magnetic Fields
Most Played Song: "Jigsaw Falling into Place" Radiohead
Most Recently Added Album: Bleach / Nirvana (reissue)

First Song Alphabetically: "A.C. Cover" Camper Van Beethoven
Last Song Alphabetically: "ZZ Top Goes to Egypt" Camper Van Beethoven
First Song Numerically: "007 (Shanty town)" Desmond Dekker
Last Song Numerically: "90-Mile Water Wall" The National
Shortest Song: "(Untitled)" Maxwell (:05)
Longest Song: "Photogram/Om Eye Sweet Isthmus" Camper Van Beethoven (19:40)

First Album Alphabetically: (a)spera / Mirah
Last Album Alphabetically: Zen Arcade / Husker Du
First Album Numerically: #1 Record/Radio City / Big Star
Last Album Numerically: 3 Rounds and Sound / Blind Pilot

First Five Songs That Pop Up On Shuffle iTunes DJ:
"Tower Song" Martha Wainwright
"Room a Thousand Years Wide" Soundgarden
"Flume" Bon Iver
"Senor 007" Ray Barretto
"Good Feeling" Violent Femmes

Conclusion: I need to get some of that Camper Van off the hard drive....

An iTunes inventory.

Number of Songs: 1891
Number of Albums: 576
Most Recently Played Song: "What are you going to do with me" by Paper Moon
Most Played Song: "Night" by Jeff Hanson
Most Recently Added Album: "Dark Was the Night" Red Hot compilation

First Song Alphabetically: "About a Song" by Nancy Sinatra
Last Song Alphabetically: "Zombie Stomp" by Ozzy Osborne
First Song Numerically: "100 yard dash" by Raphael Saadiq
Last Song Numerically: "9 to 5" by Alison Krauss
Shortest Song: "Here come the 123s" by They Might Be Giants
Longest Song: "In-A-Gadda-Da-Vida" by Iron Butterfly

First Album Alphabetically: Abbey Road, the Beatles
Last Album Alphabetically: Zen Arcade, Hüsker Dü
First Album Numerically: 3 Rounds and a Sound, Blind Pilot
Last Album Numerically: 808s and Heartbreak, Kanye West

First Five Songs That Pop Up On Shuffle:
"All Love Gone" Charlie Pickett
"Some Small History" Portastatic
"Super Trouper" ABBA
"Morning tide" The Little Ones
"She's Got My Number" Semisonic