Funny you should ask.  Aside from random tracks on the iPod and my personalized radio station on Pandora.com (this is such a great concept, and free too), here's what I've been listening to:
Sufjan Stevens, Songs for Christmas
Roy Buchanan, "The Messiah Will Come Again" and "Sweet Dreams"
Bruce Springsteen, Magic
The Avett Brothers, Mignonette

Some favorites of 2007 (more or less in order):
The Arcade Fire, Neon Bible
Bruce Springsteen, Magic
Jason Isbell, Sirens of the Ditch
The White Stripes, Icky Thump
Wilco, Sky Blue Sky
Fountains of Wayne, Traffic and Weather
Lily Allen, Alright, Still
Bettye LaVette, The Scene of the Crime
My top albums of 2006:
1. Drive-By Truckers, A Blessing and a Curse
2. Bob Dylan, Modern Times
3. Sufjan Stevens, Songs for Christmas
4. Gnarls Barkley, St. Elsewhere
5. Lucero, Rebels, Rogues & Sworn Brothers

The twenty most-played songs/artists on my iPod so far (with strong assists from the other members of my family):
Chris Brokaw, "The Fields" and "Gauntlet"
Fountains of Wayne, "I Want an Alien for Christmas"
Descendents, "I Like Food"
Josh Rouse, "It's the Nighttime," "Sad Eyes," and "Winter in the Hamptons"
The White Stripes, "Fell in Love with a Girl"
B.J. Thomas, "Raindrops Keep Falling on My Head"
Dinosaur Jr., "Little Fury Things," "Severed Lips," and "Repulsion"
Drive-By Truckers, "Zoloft"
Prince, "Kiss" and "When Doves Cry"
Bright Eyes, "First Day of My Life"
Judas Priest, "You've Got Another Thing Comin' "
Shelby Lynne, "Your Lies"
They Might Be Giants, "Boat of Car," "Don't Let's Start," and "We're the Replacements"
Bruce Springsteen, "Long Time Comin' "
Louis Jordan, "Beans and Cornbread"
Kelly Willis, "They're Blind"
Replacements, "Answering Machine"
Uncle Tupelo, "Gun"
The Meters, "Sophisticated Cissy"
The Style Council, "Headstart for Happiness"
Songs I wish were on my iPod:
Alex Chilton, "She Might Look My Way"
Amazing Rhythm Aces, "Third Rate Romance"
Focus, "Hocus Pocus"
Mary Lou Lord, "Some Jingle Jangle Morning" (single version)

My top albums of 2005 (too hard to come up with five albums in this Age of iTunes):
1. Chris Brokaw, Incredible Love
2. Josh Rouse, Nashville
3. Bruce Springsteen, Devils and Dust 

My top five albums of 2004:
1. Tegan and Sara, So Jealous
2. Drive-By Truckers, The Dirty South
3. Patterson Hood, Killers and Stars
 4. Magnetic Fields, i
5. Elliott Smith, from a basement on a hill

My top five of 2003:
1. Josh Rouse, 1972
2. Drive-By Truckers, Decoration Day
3. Fountains of Wayne, Welcome Interstate Managers
4. Shelby Lynne, Identity Crisis
5. The White Stripes, Elephant

My top five of 2002:
1. Drive-by Truckers, Southern Rock Opera
2. Bruce Springsteen, The Rising
3. Neko Case, Blacklisted
4. Linda Thompson, Fashionably Late
5. Amy Rigby, World on a Broken String

My top five of 2001:
1. The White Stripes, White Blood Cells
2. Lucinda Williams, Essence
3. Chris Brokaw, red cities
4. Bruce Springsteen & the E Street Band, Live in New York
5. Ryan Adams, Gold

My top five of 2000:
1. Aimee Mann, Bachelor No. 2
2. Belle and Sebastian, Lazy Line Painter Jane
3. Marah, Kids in Philly
4. Shelby Lynne, I Am Shelby Lynne
5. Steve Earle, Transcendental Blues

My top five of 1999:
1. Fountains of Wayne, Utopia Parkway
2. Aimee Mann, Magnolia soundtrack
3. Magnetic Fields, 69 Love Songs
4. Beck, Midnite Vultures and Mutations
5. Kelly Willis, What I Deserve

My top five of 1998:
1. Lucinda Williams, Car Wheels on a Gravel Road
2. Sarge, The Glass Intact
3. Belle and Sebastian, The Boy with the Arab Strap
4. Cheri Knight, The Northeast Kingdom
5. Elliott Smith, XO

My top ten of the 1990s (in no particular order):
Lucinda Williams, Sweet Old World
Aimee Mann, I'm With Stupid
Fountains of Wayne, Utopia Parkway
Guided By Voices, Alien Lanes
Amy Rigby, Diary of a Mod Housewife
Freedy Johnston, Can You Fly
Nirvana, MTV Unplugged in New York
Blake Babies, Sunburn
Steve Earle, I Feel Alright
Iris DeMent, My Life

Desert Island Discs ... ours go up to Eleven

Last updated on22-Dec.-2007.  My thanks to Barefoot Jim Connelly for coming up with this idea so I could steal it.