| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Happy in Hindsight | Jonny Fritz | 3:30 | |
| The Wolfman of Del Rio | Terry Allen | 5:38 | |
| Crop Comes In | Chatham County Line | 4:23 | |
| Rose from the Mountain | The Flatlanders | 2:49 | |
| Melinda Down the Line | Ian Fitzgerald | 5:06 | |
| Everybody's Missing the Sun | The Gourds | 2:59 | |
| If I Cant Win | The Cactus Blossoms | 3:17 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| If I Could Only Fly | Blaze Foley | 4:04 | |
| Lubbock Woman | Terry Allen | 3:36 | |
| She Is My Everything | John Prine | 4:25 | |
| Cry To Me | John Hiatt | 3:55 | |
| Drunken Poet's Dream | Ray Wylie Hubbard | 4:20 | |
| One Red Rose | Iris DeMent | 3:07 | |
| I've Been Gone | Zoe Muth and the Lost High Rollers | 4:28 | |
| Hard Travelin' | Watchhouse | 2:42 | |
| Illegal Smile | John Prine | 3:13 | |
| 1952 Vincent Black Lightning | The Del McCoury Band | 4:02 | |
| Wrong Time to Be Right | Sam Doores, Riley Downing, The Tumbleweeds | 4:35 | |
| Memphis Women and Chicken | Donnie Fritts | 3:51 | |
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| She Took A Lot Of Pills (And Died) | Robbie Fulks | 2:43 | |
| There Oughta Be a Law Against Sunny Southern California (Jabo I, II, III) | Terry Allen | 4:29 | |
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| In My Own Mind | Lyle Lovett | 5:36 | |
| It Ain't Over Yet | Rodney Crowell, Rosanne Cash, John Paul White | 5:14 | |
| Carl Perkins' Cadillac | Drive-By Truckers | 5:26 | |
| James Alley Blues | Willie Watson | 4:06 | |
| Helen's Restaurant | Daniel Romano | 2:43 | |
| Mama Needs a Margarita | Zoe Muth | 4:06 | |
| Sometimes | Luke Bell | 4:07 | |
| Hundred Dollar Valentine | Chris Smither | 3:05 | |
| My Old Drunk Friend | Freakwater | 3:33 | |
| Wishing All These Things Were New | Merle Haggard | 3:20 | |
| Lonesome Old River Blues | Dom Flemons | 2:42 | |
| Speed Of The Sound Of Loneliness | John Prine | 3:28 | |
| Satin Sheets | Willis Alan Ramsey | 2:39 | |
| The Road Goes On Forever | Joe Ely | 4:33 | |
| Let It Ride | Ryan Adams & The Cardinals | 3:23 | |
| One Good Year | Slaid Cleaves | 4:26 | |
| I Wish It Would Rain | Rodney Crowell | 3:28 | |
| Too Drunk To Dream | Whiskeytown | 2:53 | |
| Long Black Veil - Remastered 2000 | The Band | 3:01 | |
| I Lost It | Lucinda Williams | 3:31 | |
| Colorado | The Flying Burrito Brothers | 4:52 | |
| (Iām Gonna Get Over This) Some Day | Logan Ledger | 2:52 | |
| Willin' | Linda Ronstadt | 3:02 | |
| Monster Truck | Ramsay Midwood | 3:30 | |
| Goodbye Old Missoula | Willis Alan Ramsey | 5:03 | |
