| On the Banks of the Old Kishwaukee | Ryley Walker | 5:00 | |
| You've Got Me Where You Want Me | Chuck Prophet | 3:27 | |
| Coconut Tree (with Willie Nelson) | Kenny Chesney, Willie Nelson | 3:24 | |
| Blue Eyes Crying In the Rain | Willie Nelson | 2:18 | |
| Detroit or Buffalo | Barbara Keith | 4:31 | |
| The Battle (feat. Ryan Adams) | Caitlin Cary, Ryan Adams | 3:00 | |
| Señor (Tales of Yankee Power) | Willie Nelson, Calexico | 5:17 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| When the Circus Comes | Los Lobos | 3:16 | |
| Old Shoes | Tom Waits | 4:25 | |
| Let the Mystery Be | 10,000 Maniacs | 3:08 | |
| Cowboys Are Frequently Secretly Fond Of Each Other | Orville Peck, Willie Nelson | 3:38 | |
| River Floor | Joe Henry | 4:34 | |
| Angel from Montgomery | Bonnie Raitt | 4:11 | |
| If I Could Only Fly | Blaze Foley | 4:04 | |
| Whatever Happened to Rose | Bob Weir | 4:19 | |
| What's So Funny 'Bout Peace, Love and Understanding? | Nick Lowe | 4:03 | |
| Worried Mind | Eilen Jewell | 3:15 | |
| Wichita Ain't so Far Away | The Delines | 2:31 | |
| No Regrets - 2008 Remaster | Tom Rush | 3:51 | |
| The Rosarita Beach Cafe | Warren Zevon | 4:09 | |
| Unlock more with Songs Like X Pro |
| Silver Wings | Merle Haggard, Willie Nelson | 3:41 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| Wrote A Song For Everyone | Mavis Staples | 3:47 | |
| Me and Bobby McGee | Kris Kristofferson | 4:20 | |
| Astral Weeks - 1999 Remaster | Van Morrison | 7:06 | |
| Time To Move On | Tom Petty | 3:15 | |
| One More River to Cross | Bob Weir | 4:05 | |
| What Do We Do Now | John Hiatt | 2:58 | |
| Brothers | Mary Gauthier | 2:50 | |
| Ramblin' Kind | Jack Klatt | 2:51 | |
| Just One Love | Kimmie Rhodes, Willie Nelson | 4:19 | |
| Square One | Tom Petty | 3:24 | |
| In Your Own Time | Calexico, Iron & Wine | 3:09 | |
| Mammas Don't Let Your Babies Grow up to Be Cowboys | Waylon Jennings, Willie Nelson | 2:32 | |
| Wait for Me (feat. Sam Beam) | Tift Merritt, Sam Beam | 4:32 | |
| Early Mornin' Rain | Gordon Lightfoot | 3:08 | |
| I Wish It Would Rain | Rodney Crowell | 3:28 | |
| Trampoline | Joe Henry | 4:33 | |
| Through the Morning, Through the Night | Robert Plant, Alison Krauss | 4:00 | |
| The Night They Drove Old Dixie Down | The Band | 3:31 | |
| The Weary Kind | Ryan Bingham | 4:18 | |
| Wide River To Cross | Levon Helm | 4:51 | |
| El Camino Reprise | Amos Lee, Willie Nelson | 4:14 | |
| Superman | Snoop Dogg, Willie Nelson | 2:05 | |
| Follow | Richie Havens | 6:20 | |
| You Can't Fail Me Now | Loudon Wainwright III | 3:45 | |
| Golden Bird | Levon Helm | 5:11 | |
| Just Outside Of Austin | Lukas Nelson and Promise of the Real | 4:44 | |
