Why not...

iPod!
Sort by song name - first:
- 'Deed I do - Diana Krall
- 's Wonderful - Diana Krall
- 's Wonderful - Ella Fitzgerald
- #@$%! - Pressure Cooker
- (Dont You Mess Around With) My Little Sister - Michelle Shocked

Sort by time - shortest:
- haha - I have 2 songs at "0:00" - not linked properly, apparently
- #@$%! - Pressure Cooker
- Band Intro - David Bowie
- Her Majesty - Beatles (quite lovely, actually!)
- Riker's Mailbox - Phish
And, the ever-brilliant:
- Triple Track (Live) - Dance Hall Crashers
--> Overall, I have 21 tracks (not counting the zeros) under a minute, and another favorite is Bowie's "Don't Site Down" off of the Space Oddity album

Sort by time - longest:
I have some nice new-agey / meditation music here:
- Compassion by Peter Kater (1:15:10)
- Reiki by The Light Touch (1:02:01)
- The Mystik Dance on the El Hadra album (52:27)
- Quiet Waters on the Mystic Flute album (30:01)
- Sonate pour piano et alto en A major - by Cesar Fanck (29:13)
And, of more "mainstream-esque" stuff, next comes:
- Echoes - Pink Floyd


Sort by artist - first:
- µ-Ziq
- a-Ha
- ABBA
- AKA Rudie w/Emma Grandillo (from Mashin UP the Nation comp)
- Alabama 3 (from A Life Less Ordinary sountrack)


Sort by artist - last:
- Zoot Sims
- Zoe Hart (Les Mis sountrack)
- Yves Montand
- Wine Field (local Boston band)
- The Who


Sort by album - first:
- 24 Nights - Clapton
- 2400 Fulton Street - Jefferson Airplane
- A Farewell to Kings - Rush
- A Hard Day's Night - Beatles
- A Life Less Ordinary - soundtrack


Sort by album - last:
- Zoot Suit Riot - Cherry Poppin' Daddies
- Zone Unknown - Gabrielle Roth
- Ziggy Stardust - Bowie
- Yves Chante Jaques Prevert - Montand
- Yes - Morphine


Top Five Most Played Songs:
3 tied for first place:
- Monkey in the Moon - Alphaville
- Guardian Angel - Alphaville
- In These Shoes? - Kirsty MacColl
12 tied for next place, including Alphaville, Barenaked Ladies, CSNY, Depeche Mode, Eek A Mouse, Erasure, James Taylor, k.d. Lang, Marillion, No Doubt, Spacehog

First five songs that come up on Shuffle:
- Gloria - U2
- Stratosphere - Jimmie Lunceford And His Orchestra
- Taxi War Dance - Count Basie & His Orchestra
- Warm Sporran - Jethro Tull
- Friend of the Devil - Grateful Dead