| Trouble | Little Feat | 2:17 | |
| Table For One | Courtney Marie Andrews | 3:59 | |
| Mammas Don't Let Your Babies Grow up to Be Cowboys | Waylon Jennings, Willie Nelson | 2:32 | |
| Me and Bobby McGee | Kris Kristofferson | 4:20 | |
| Dusty Boxcar Wall | Eilen Jewell | 2:43 | |
| Lay Me Down (with Willie Nelson) | Loretta Lynn, Willie Nelson | 2:50 | |
| Old Shoes | Tom Waits | 4:25 | |
| Willin' | Little Feat | 2:54 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Walking Each Other Home | Mary Gauthier | 4:17 | |
| Die When I'm High (Halfway to Heaven) | Particle Kid, Micah Nelson, Willie Nelson | 3:32 | |
| Reckless | Rodney Crowell | 3:30 | |
| States I'm In | Bruce Cockburn | 5:42 | |
| True Love Travels on a Gravel Road | Nick Lowe | 3:36 | |
| Midnight Rider | Willie Nelson | 2:50 | |
| Pontchartrain | Anders Osborne | 4:47 | |
| Hold On | Tom Waits | 5:33 | |
| I'm Not Afraid To Die | Gillian Welch, Willie Nelson | 3:54 | |
| Heaven and Hell | Waylon Jennings, Willie Nelson | 1:38 | |
| I Was Drunk | Alejandro Escovedo | 4:53 | |
| When Will I Be Changed (feat. Bob Weir) | Josh Ritter, Bob Weir | 5:52 | |
| Unlock more with Songs Like X Pro |
| Myrna Lee | Blue Mountain | 3:45 | |
| Señor (Tales of Yankee Power) | Willie Nelson, Calexico | 5:17 | |
| See It Through | The Cactus Blossoms | 3:59 | |
| Ballad of Easy Rider | The Byrds | 2:04 | |
| Irish Girl | Mike Campbell & The Dirty Knobs | 4:25 | |
| History of Lovers | Calexico, Iron & Wine | 3:09 | |
| Rexanimarum | Israel Nash | 4:59 | |
| Come On Up To The House | Willie Nelson, Sheryl Crow, Lukas Nelson | 5:16 | |
| Lost My Drivin' Wheel | Tom Rush | 5:20 | |
| The Battle (feat. Ryan Adams) | Caitlin Cary, Ryan Adams | 3:00 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| The Night Shift Lullaby | Magnolia Electric Co., Jason Molina | 4:33 | |
| Funny 'Bout Love | Ray Bonneville | 3:44 | |
| Into the Mystic - 2013 Remaster | Van Morrison | 3:25 | |
| Crawling Back To You | Tom Petty | 5:05 | |
| Oh My Sweet Carolina | Ryan Adams | 4:56 | |
| Turn Off The News (Build A Garden) | Lukas Nelson and Promise of the Real | 3:43 | |
| Six O'Clock News | Kathleen Edwards | 4:36 | |
| The Rock Of My Soul | Rodney Crowell | 4:50 | |
| Bottom Of The World | Alejandro Escovedo | 3:04 | |
| I Just Can't Let You Say Good-Bye | Willie Nelson | 4:38 | |
| Sweet Somewhere Bound | Jackie Greene | 4:59 | |
| You Can't Fail Me Now | Loudon Wainwright III | 3:45 | |
| Funny How Time Slips Away | Glen Campbell, Willie Nelson | 3:32 | |
| When I Get A Little Money | Chris Hillman | 2:32 | |
| Crazy | Carla Bruni, Willie Nelson | 3:03 | |
| Raise The Dead | Colvin & Earle | 2:51 | |
| Sonora's Death Row | Leo Kottke | 4:32 | |
