| I Still Miss Someone | John Doe, The Sadies | 2:19 | |
| Dead Skunk | Loudon Wainwright III | 3:05 | |
| Dooley | The Gourds | 1:56 | |
| Statistician's Blues | Todd Snider | 2:57 | |
| Honky Red | Murray McLauchlan | 3:58 | |
| Jesus & Elvis | Greg Brown | 3:38 | |
| The Nail | Sarah Shook & the Disarmers | 3:13 | |
| My Old Drunk Friend | Freakwater | 3:33 | |
| I've Been Gone | Zoe Muth and the Lost High Rollers | 4:28 | |
| Stop the World and Let Me Off | John Doe, The Sadies | 3:42 | |
| Fought the Blues and Won | The Deslondes | 3:29 | |
| Tell Me Mama, Tell Me Right | Jackie Greene | 2:38 | |
| If I Had Known | Greg Brown | 3:25 | |
| West Nashville Grand Ballroom Gown | Todd Snider | 4:29 | |
| Chase the Feeling | Kris Kristofferson | 4:06 | |
| House of the White Rose Boquet | Ray Wylie Hubbard | 3:23 | |
| Only the Song Survives | John Hiatt | 4:00 | |
| Amarillo Highway | Robert Earl Keen | 2:27 | |
| Things Could Get Much Worse | Jeremy Ivey | 3:26 | |
| Levelland | James McMurtry | 5:23 | |
| Old Mexico | Marty Stuart And His Fabulous Superlatives | 2:45 | |
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| Dead Flowers | The Brothers Comatose | 5:08 | |
| Black Rose | Billy Joe Shaver | 2:44 | |
| Luxury Liner | The International Submarine Band | 2:48 | |
| You Might Be Wrong | Paul Thorn | 3:29 | |
| Hard Life | Aaron Lee Tasjan | 2:44 | |
| Wasteland of the Free | Iris DeMent | 5:15 | |
| Statistician's Blues - Live | Todd Snider | 2:57 | |
| Leaving Louisiana in the Broad Daylight | Shovels & Rope | 3:33 | |
| Shut up and Sing | Cody Canada & The Departed, Todd Snider, Kaitlin Butts | 3:09 | |
| Worry Too Much | Buddy Miller | 4:48 | |
| Mostly Water | Bap Kennedy | 3:23 | |
| Cold Beer Hello | The V-Roys | 3:34 | |
| Drunken Barber's Hand | Slaid Cleaves | 2:41 | |
| Black Dog | Blue Mountain | 2:34 | |
| Are You Sure Hank Done It This Way | The Mavericks | 3:55 | |
| Fifteen Passenger Van | Jonny Fritz | 2:05 | |
| I Wish We Had Our Time Again | Todd Snider | 2:28 | |
| Way Out West | Marty Stuart And His Fabulous Superlatives | 5:41 | |
| The Midnight Special | Billy Bragg, Joe Henry | 3:34 | |
| Wavin' My Heart Goodbye | The Flatlanders | 2:38 | |
| Big Cheeseburgers and Good French Fries | Gurf Morlix | 2:51 | |
| Valley Road | James McMurtry | 4:45 | |
| Feed My Monkey | Ramsay Midwood | 3:18 | |
| Bad Liver And A Broken Heart | Hayes Carll | 4:22 | |
| A Kiss Before I Go | Ryan Adams & The Cardinals | 2:04 | |
| Lily, Rosemary and the Jack of Hearts | Tom Russell | 9:44 | |
| Airline Agent | James McMurtry | 3:11 | |
| I Wish It Would Rain | Rodney Crowell | 3:28 | |