| Whiskey Bottle | Uncle Tupelo | 4:46 | |
| Laminated Cat | Jeff Tweedy | 3:49 | |
| Borderline | Eliza Gilkyson | 2:42 | |
| Cigarettes Coffee and Booze | The Minus 5 | 4:24 | |
| The Way I Love Her | Bap Kennedy | 3:30 | |
| Hasten Down the Wind | Warren Zevon | 2:32 | |
| Drag Queens In Limousines | Mary Gauthier | 5:39 | |
| Sunday Morning (feat. Billy Bragg & Courtney Barnett) | RocKwiz, Billy Bragg, Courtney Barnett | 2:53 | |
| Oh, Mama, Come Home | Jakob Dylan | 2:26 | |
| True Love Travels on a Gravel Road | Nick Lowe | 3:36 | |
| The Panama Limited | Tom Rush | 8:23 | |
| Dusty Boxcar Wall | Eilen Jewell | 2:43 | |
| Just Us Kids | James McMurtry | 5:08 | |
| The Whole Night Sky | Bruce Cockburn | 3:54 | |
| Lonesome Old River Blues | Dom Flemons | 2:42 | |
| Melinda Down the Line | Ian Fitzgerald | 5:06 | |
| Simple Twist of Fate | Jeff Tweedy | 3:43 | |
| Workin’s Too Hard | Rayna Gellert | 3:36 | |
| Everybody's Missing the Sun | The Gourds | 2:59 | |
| The Ballad of the Opening Band | Jeff Tweedy | 4:27 | |
| Atomic Power | Uncle Tupelo | 1:52 | |
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| Down on Penny's Farm | Natalie Merchant | 3:43 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
| The Swimming Song | Loudon Wainwright III | 2:27 | |
| Wear Me Out | Jesse Winchester | 2:37 | |
| Rain Roll In | Eilen Jewell | 2:47 | |
| Acuff-Rose | Uncle Tupelo | 2:35 | |
| Ditch | Sam Baker | 1:56 | |
| Ain't Gonna Worry No More | Peter Case | 6:14 | |
| Wasteland of the Free | Iris DeMent | 5:15 | |
| Simple Gearle | Stacey Earle | 2:30 | |
| Till I'm Too Old to Die Young (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:29 | |
| New Madrid | Uncle Tupelo | 3:31 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Bumble Bee | Peter Case | 3:34 | |
| The Brand New Tennessee Waltz | Jesse Winchester | 3:08 | |
| Love Will Win the War | Darden Smith | 3:54 | |
| Put Down The Gun | Peter Case | 3:41 | |
| Forever Has Come To An End | Buddy & Julie Miller | 2:50 | |
| The Winner | Kris Kristofferson | 4:58 | |
| Daughter | Loudon Wainwright III | 3:32 | |
| Listening To The Wind That Blows | Billy Bragg, Wilco | 5:03 | |
| Raise The Dead | Colvin & Earle | 2:51 | |
| Ingrid Bergman | Billy Bragg, Wilco | 1:50 | |
| Let It Ride | Ryan Adams & The Cardinals | 3:23 | |
| Another Free Woman | Blackie & The Rodeo Kings, Sara Watkins | 3:30 | |
| Christ For President | Billy Bragg, Wilco | 2:42 | |
| Lebanon, Tennessee | Ron Sexsmith | 2:57 | |
