| New Ways to Fail | Sarah Shook & the Disarmers | 4:07 | |
| Got Your Six | Mary Gauthier | 2:38 | |
| Moonshiner | Uncle Tupelo | 4:23 | |
| The Battle (feat. Ryan Adams) | Caitlin Cary, Ryan Adams | 3:00 | |
| Hard to Be an Outlaw (feat. Willie Nelson) | Billy Joe Shaver, Willie Nelson | 3:06 | |
| You Got to Me | James McMurtry | 5:23 | |
| Amanda's Song | Adam Carroll | 2:57 | |
| Salome | Old 97's | 4:07 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| Chickamauga | Uncle Tupelo | 3:42 | |
| Undone | Yarn | 3:27 | |
| On the Ropes | The Honeycutters | 3:15 | |
| Shores of Galilee | Shinyribs | 4:43 | |
| Black Dog | Blue Mountain | 2:34 | |
| Restless | James McMurtry | 5:15 | |
| Velvet Guitar | Alejandro Escovedo | 4:23 | |
| A Pretty Good Guy | Chris Knight | 2:27 | |
| Over You | Sarah Shook & the Disarmers | 3:11 | |
| Bernadine (feat. Chris Carroll) | Adam Carroll, Chris Carroll | 4:31 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Hooky Junk | The Gourds | 4:43 | |
| Unlock more with Songs Like X Pro |
| Dead Flowers | The Brothers Comatose | 5:08 | |
| Just Us Kids | James McMurtry | 5:08 | |
| Cigarettes Coffee and Booze | The Minus 5 | 4:24 | |
| After the Rain | Chuck Prophet | 3:35 | |
| I Like Trains | Fred Eaglesmith | 3:30 | |
| Wishing All These Things Were New | Merle Haggard | 3:20 | |
| The Prettiest Thing | The Modern Don Juans, David Childers | 4:14 | |
| Jimmy Carter | Blue Mountain | 2:24 | |
| Castanets | Alejandro Escovedo | 3:27 | |
| Devilsong | Shinyribs | 4:33 | |
| The Most Unoriginal Sin | John Hiatt & The Goners | 4:15 | |
| Daydreamer | John Fullbright | 4:32 | |
| Forgotten Coast | James McMurtry | 3:34 | |
| City Flower | Jeffrey Foucault | 3:38 | |
| The Way We Are | The Flatlanders | 3:12 | |
| Starts With You | American Aquarium | 3:48 | |
| Life Worth Livin' | Uncle Tupelo | 3:32 | |
| All The Lilacs In Ohio | John Hiatt, Jerry Douglas | 3:29 | |
| Take Me to Lake Charles | Shinyribs | 3:16 | |
| Okeechobee | Wrinkle Neck Mules | 4:23 | |
| Little Victories | Chris Knight | 3:00 | |
| Lazy Guy | Slobberbone | 4:18 | |
| Excuse Me While I Break My Own Heart Tonight - Faithless Street Album Version | Whiskeytown | 3:20 | |
| Ethylene | John Hiatt | 4:03 | |
| Midway Park | Whiskeytown | 3:23 | |
| Let It Ride | Ryan Adams & The Cardinals | 3:23 | |
| Lily, Rosemary and the Jack of Hearts | Tom Russell | 9:44 | |
| Fancy Boys | Ray Wylie Hubbard, Hayes Carll, James McMurtry, Dalton Domino | 3:09 | |
