| 12/17/99 Playlist | ||
| Artist | Song | Album |
| Waco Brothers | Revolution Blues | Do You Think About Me? |
| Derailers | Pawnshop Wedding Rings | Reverb Deluxe |
| Hangdogs (!) | The Ring | East of Yesterday |
| Dave Alvin | Wanda & Duane | Blue Blvd |
| Steve Earle | I Ain't Ever Satisfied | Exit 0 (!!) |
| Infidels | The Old Story | advance promo |
| Groobees | Ahead of Time ® | The Groobees |
| Jerry Jeff Walker ® | Lovin' Makes Livin' Worthwhile | Live at Gruene Hall |
| Beau Jocque | Hot Tamale Baby | Zydeco Giant |
| James Brown | I Guess I'll Have to Cry, Cry, Cry | Say It Live and Loud, Live in Dallas 8.26.68 |
| Texas Tornados | Laredo Rose ® | Texas Tornados |
| Road Kings | Boystown | Road Kings |
| Steve Earle | Week of Living Dangerously | Exit 0 |
| James McMurtry | Safe Side ® | Candyland |
| Van Wilks (!) | Boystown | Soul of A Man |
| Long John Hunter | Trouble on the Line | Swingin' From the Rafters |
| Van Wilks | Goin' To See My Baby | Soul of A Man ® |
| Derailers ® | Long on Love | Full Western Dress |
| Randy Garibay | Chicano USA ® | Chicano Blues Man |
| Beausoleil | Cajunization Blues | Cajunization |
| Kevin Johnson & the Linemen | Miss Lonelyhearts Out On The Town | Edges From The Postcard 2 |
| Robbie Fulks | Stone River | " |
| Brent Mitchell | Take Me Back Home | Fallen Angel Palace |
| Zachary Richard | Come On Sheila | Snake Bite Love |
| Stephen Bruton | Bluebonnet Blue ® | Right on Time |
| James McMurtry | Paris ® | It Had To Happen |
| Larry Joe Taylor | Third Coast ® | First Row, Third Coast |
| Robert Earl Keen | The Front Porch Song ® | The Live Album |
| Chubby Carrier | Fire on the Mountain | Too Hot To Handle |
| Meters | Fire on the Bayou | Uptown Rulers: Live on the Queen Mary |
| Webb Wilder | The Olde Elephant Man | Acres of Suede |
| Los #3 Dinners | Good Man ® | Quiero Un Camaro! |
| Whiskeytown | Top Dollar | Faithless Street |
| Lyle Lovett | Sold American (!) | Pearls in the Snow: Tribute to Kinky Friedman |
| Slobberbone | Piece of Crap | This Note's For You Too! |
| Neil Young | Greensleeves | |
| Toni Price ® | Just To Hear Your Voice | Swim Away |
| Bottle Rockets | Brand New Year | Brand New Year |
| Nathan Abshire | Pine Grove Blues | Alligator Stomp Vol 2: Cajun & Zydeco Classics |
| Leeann Atherton | Drift On | Lady Liberty |
| Sisters Morales | Couldn't Help But Love You | Ain't No Perfect Diamond |
| Adam Carroll (!) | Cole | South of Town |
| Infidels | Time of the End | advance promo |
| James McMurtry | Rayolight | Where'd You Hide The Body |
| Luke Olson | City of Dreams | Panhandle Sunset |
| Trish Murphy (!) | I Know What You Are | Rubies on the Lawn |
| Cave Catt Sammy | My Baby | Fast Cars & Smoky Bars |
| Pat Green | The Bottle | Dancehall Dreamer |
| Jon Dee Graham | Lucky Moon | Summerland |
| Monte Montgomery | When Will I | Lost & Found |
| Hank Williams III | If The Shoe Fits ® | Risin' Outlaw |
| C.J. Chenier | Au Contraire, Mon Frere | The Big Squeeze ® |
| Steve Earle | San Antonio Girl | Exit 0 |
(® = requested song/artist; (!) = positive listener response)