Mine:
1) Desmond Dekker and The Aces - "Problems"
2) Beastie Boys - "Shadrach"
3) Bad Religion - "We're Only Gonna Die"
4) RJD2 - "Silver Fox"
5) Tortoise - "The Taut And Tame"
6) The Breeders - "No Aloha"
7) Illogic - "I Wish He Would Make Me"
8) The Bouncing Souls - "East Side Mags"
9) Tom Waits - "Christmas Card From a Hooker in Minneapolis"
10) Eric B. & Rakim - "Extended Beat"

1. Mark Knopfler -- "Coyote"
2. Ella Fitzgerald - "Ten Cents a Dance"
3. Adele - "Rolling in the Deep"
4. Shawn Colvin - "Words"
5. Piano Red - "The Wrong Yo-Yo"
6. J.S. Bach -Cantata No. 21
7. Sarah Vaughan - "Great Day"
8. J.S. Bach - Orchestral Suite #2 in B Minor
9. Champion Jack Dupree - "Walking the Blues"
10. Indigo Girls - "Left Me a Fool"

I tend to do "manual shuffling" (it's the last vestige of my history as a radio DJ... I DON'T WANT TO BE PREPROGRAMMED) so here's what I've recently assembled

Elton John - Funeral for a Friend/Love Lies Bleeding

Madness - One Step Beyond

Pseudo Echo - Funky Town
the GOOD version...

My Favorite Things - John Coltrane

Joan Armatrading - Drop The Pilot

Moody Blues - Nights in White Satin (Breathe deep the gathering gloom...)

Yes - Leave It

Weird Al Yankovic - Albuquerque
yes, I can't do this without a little Weird Al... 11:23 of 'a little'

Do It Again... but I can't decide...
Steely Dan, Beach Boys or Kinks?

heck, if I'm gonna 'go long', I might as well: Iron Butterfly - In A Gadda Da Vida

1. Lucinda Williams - Blue
2. The Pretenders - 2000 Miles
3. Mitch Ryder - Jenny Take a Ride
4. Thea Gilmore - The Gambler
5. Grateful Dead - Black Peter
6. Josh Ritter - Leaving
7. Leonard Cohen - Heart With No Companion
8. Kasey Chambers - A Million Tears
9. Grateful Dead - Sugar Magnolia
10. David Bowie - Cracked Actor

Here's Mine:

1. Memphis Minnie: Outdoor Blues
2. Joni Mitchell: Twisted
3. Matraca Berg: Back When We Were Beautiful
4. Bruce Robison: Blame it On Me
5. Bettye Lavette: The Scene of the Crime
6. The Wrights: I Feel the Blues Moving In
7. Nina Simone: See Line Woman
8. Ola Belle Reed: Springtime of Life
9. Etta James: Cry Me a River
10. Loretta Lynn: The Pill

1. Billie Holiday - "I Can't Give You Anything but Love"
2. Neko Case - "Never Turn Your Back on Mother Earth"
3. Billie Holiday - "This Year's Kisses"
4. Patty Griffin - "Cold As It Gets"
5. Sublime - "Santeria"
6. Soltero - "Paradise City"
7. Billie Holiday - "Fine and Mellow"
8. Billie Holiday - "Let's Do It"
9. Erykah Badu - "Apple Tree"
10. Joni Mitchell - "Michael from Mountains"

I'm glad it's not just my imagination -- I actually made several Billie Holiday-free playlists because I thought iTunes was playing way too much of her.

U2 - Cedars Of Lebanon
Kaiser Cartel -- Carroll Street Station
Sean Lennon - Falling Out of Love
Simple Minds - All The Things She Said
Teenage Fanclub - Here Comes Your Man
The Brian Jonestown Massacre - I've Been Waiting
Peder - The Sour (Featuring Dean Bowman)
Bjork & Tricky - Black Coffee
The Bootleague Groove is in the Black Hole Sun (a mashup)
Jill Barber - Be My Man (clipped youtube clip)

Choirboys - All Night Long
Blood, Sweat & Tears - I Can't Quit Her
Air Supply - All Out Of Love
INXS - This Time
10cc - I'm Mandy, Fly Me
The Doors - Strange Days
Skyhooks - Horror Movie
Hoodoo Gurus - What's My Scene?
Pink Floyd - Marooned
U2 - Staring at the Sun
Matchbox 20 - Bright Lights
Bob Dylan - Hurricane
Green Day - Android
Billy Joel - All About Soul
Gary Numan - Random
Pink Floyd - When the Tigers Broke Free
Noiseworks - Hot Chilli Woman
Fleetwood Mac - Hold Me
Smokey Robinson & The Miracles - The Tracks of My Tears
John Butler Trio - Company Sin
The Eagles - The Last Resort

Yeah, more than 10, but I kept going in search of more than a couple from this century. No such luck, apparently.