| December, 1999 | Jolie Holland | 3:36 | ||
| Hills of Mexico | Jake Xerxes Fussell | 5:51 | ||
| Of Raymond | Lambchop | 3:02 | ||
| Playthings | Palace Brothers | 2:06 | ||
| A Chance Counsel | Richard Buckner | 4:50 | ||
| Interstate | Rivulets | 2:01 | ||
| Daniella | Hurray For The Riff Raff | 4:03 | ||
| Sky Blue | Townes Van Zandt | 2:31 | ||
| Even Though | Joan Shelley | 3:20 | ||
| Only Someone Running | Will Oldham | 3:02 | ||
| Out Beyond | Luluc | 3:30 | ||
| You Never Wanted Me | Jackson C. Frank | 3:07 | ||
| The Golden Willow Tree | Jake Xerxes Fussell | 9:10 | ||
| Haven | Joan Shelley | 1:44 | ||
| He Told Her the City Was Killing Him | The Delines | 4:11 | ||
| Come Together | Shannon Lay | 2:39 | ||
| El Capitan | Will Johnson | 3:14 | ||
| An Empty Corner | Wilco | 3:46 | ||
| Hill Hidden Nog | Little Wings | 2:39 | ||
| Chinaberry Tree | Vic Chesnutt | 4:10 | ||
| The Sway | Joan Shelley | 3:22 | ||
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| Meridian, Ms | Phosphorescent | 2:16 | ||
| Ain't Worth the Gettin' | Timber Timbre | 3:50 | ||
| Hands for the Harvest | H.C. McEntire | 4:17 | ||
| The Glory Goes | Will Oldham | 3:17 | ||
| I Was Young When I Left Home | Antony, Bryce Dessner | 4:55 | ||
| Beneath The Rose | Micah P. Hinson | 2:56 | ||
| Star Girl | Jake Xerxes Fussell | 4:04 | ||
| Original Goodness | Marina Allen | 2:11 | ||
| I Tried To Stay Healthy For You | Palace Brothers | 3:30 | ||
| Drink My Rivers | Andy Shauf | 4:22 | ||
| Involuntary | M. Ward | 4:03 | ||
| The Fading | Joan Shelley | 3:09 | ||
| Swell Does the Skull | Aldous Harding | 5:48 | ||
| Michigan Girls | Califone | 4:00 | ||
| Before It All Went Wrong | Spain | 3:36 | ||
| Morning Dove | Julie Byrne | 2:59 | ||
| Blue Vein | Lael Neale | 4:22 | ||
| Life#2 | Lambchop | 4:43 | ||
| Green Rocky Road | Karen Dalton | 3:22 | ||
| Cover Me With Roses (1975) | Jackson C. Frank | 2:17 | ||
| No More Workhorse Blues | Palace Brothers | 3:29 | ||
| Fighting_talk | This Is The Kit | 4:24 | ||
| Step Away | Joanna Sternberg | 2:49 | ||
| The Door | Joan Shelley | 4:36 | ||
| John's Glass Eye | Iron & Wine | 1:40 | ||
| Just Like That | Grace Cummings | 1:08 | ||
| The Wheel of Fortune | Josephine Foster | 5:11 | ||
| I Feel Bonnie - feat. Bonnie 'Prince' Billy | Hot Chip, Will Oldham, Joe Goddard | 5:29 | ||
