Random play lists don’t really seem to reflect the music you really like, just music you like enough to store. It’s more interesting to know what you’re listening to now, or like the best.
So how about a non-random sampling of one of your play lists? Either the most recent one, or one you like a lot, up to 50-75 songs.
This is my most recent(I didn’t save the Xmas music list):
Bis “Dead Wrestlers”
Aberdeen City “God is Going To Get Sick of Me” (I love this song…their other songs, not so much.)
Alannah Myles “Black Velvet” (thanks to the Canadian thread)
Aqualung “Good Times Gonna Come”
Ben Lee “Into The Dark”
Bob Mould “Circles”
Butch Walker “Mixtape”
Calla “This Better Go as Planned”
Closer “Nothing Learned”
Cold “Happens All The Time”
Crossfade “Colors”
Damien Rice “Volcanos”
Depeche Mode “Precious”
dios(malos) “Going Home”
Earlimart “Heaven Adores You”
Eels “Jelly Dancers”
Eighteen Visions “I Let Go”
Elbow “The Everthere”
Finch “Bitemarks and Bloodstains”
Finest Dearest “Idaho”
Franz Ferdinand “Love and Destroy”
Franz Ferdinand “The Fallen”
Goldfrapp “Number 1”
Gomez “Nothing is Wrong”
Good Charlote “Boys and Girls”
Gorillaz “All Along” (they’re starting to grow on me)
Gravenhurst “The Velvet Cell”
Harvey Danger “Cream and Bastards Rise”
Hawthorne Heights “Nicki FM”
Hawthorne Heights “Silver Bullet”
Heather Duby “What You Thought”
Her Space Holiday “Missed Medicine” (see also, Aberdeen City)
Jack’s Manquin “The Mix Tape”
Lacuna Coil “Heaven’s a Lie”
Lemon Jelly " '79 AKA The Shouty track"
Linkin Park “Hit The Floor”
Linkin Park “Lying From You”
Lostprophets “We Still Kill The Old Way”
My Chemical Romance “Hang 'em High”
Nickelback “Someday”
Rise Against “Swing Life Away”
Seether “Truth”
Seven Channels “Breathe”
Shinedown “Fly From The Inside”
Slipknot “Vermillion pt 2” (now I like 2 songs by them)
Smile Empty Soul “Nowhere Kids”
Smoosh “It’s Cold”
Sum41 “I’m Not The One”
The Alaskan Pipeline"Grandfather Clock"
The Bravery “An Honest Mistake”
The Heads “Damage That I’ve Done”
The Information “Getting Even”
The Toadies “I Come From the Water”
The Vacancy “Blue Eyes”
The Vacancy “In The Backseat”
The Veronicas “4ever”
Trapt “Stand Up”
Weezer “We Are All On Drugs”
Alas, the majority of my play lists for the past 2 years were ruined this fall when I had a new hard drive put in, and it’s harder to recreate them from CDRs full of MP3s than I thought it would be 
Is there a way to get XP to tell you when you added a song to your computer’s hard drive like just about every other file you put on it? I can’t find an option for “sort by modified” for music.