| Jenny Reprise | Chip Taylor, Carrie Rodriguez | 3:33 | |
| Get a Little Gonner | Bill Kirchen | 2:44 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| You're Still On My Mind | Carrie Rodriguez | 2:56 | |
| Goin' Down to Memphis | Townes Van Zandt | 4:11 | |
| Free the Wind | The Flatlanders | 3:08 | |
| Freight Train | Fred Eaglesmith | 2:47 | |
| Great American Roadside | Otis Gibbs | 2:49 | |
| Air Mail Special | Marty Stuart And His Fabulous Superlatives | 2:16 | |
| Winsome Smile | Chris Smither | 3:34 | |
| Must Be the Whiskey | Chip Taylor, Carrie Rodriguez | 3:59 | |
| Flycatcher Jack and the Whippoorwill's Song (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 4:01 | |
| Oh Hally Lou | Terry Allen, The Panhandle Mystery Band | 2:01 | |
| Wishing for a Rainbow | The Flatlanders | 4:21 | |
| Semi-truck | Bill Kirchen | 2:10 | |
| Short Hair Woman | Justin Townes Earle | 2:49 | |
| Honky Tonks and Taverns | Lillie Mae | 2:19 | |
| Jesus & Elvis | Greg Brown | 3:38 | |
| Now It's Now Again | The Flatlanders | 3:33 | |
| Flat Top Guitar | Ana Egge | 2:50 | |
| Sweet Evangelina | Hoyt Axton | 3:11 | |
| Unlock more with Songs Like X Pro |
| Borderless Love | The Flatlanders | 3:16 | |
| I Don't Know Anybody in This Town | Greg Brown | 3:27 | |
| I Push Right Over | Robbie Fulks | 2:19 | |
| Keep the Home Fires Burnin' | Sarah Shook & the Disarmers | 3:03 | |
| Rocks into Sand | Bill Kirchen | 3:26 | |
| Somewhere in the Middle (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 2:41 | |
| I'd Be Lonesome | Robbie Fulks | 2:47 | |
| Adios Maria | The Cactus Blossoms | 4:09 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Cold Day in Hell | Lucinda Williams | 5:16 | |
| I Don't Work That Cheap | Bill Kirchen, Commander Cody | 2:52 | |
| Baby Do You Love Me Still? | The Flatlanders | 2:55 | |
| Big River | Darrell Scott | 3:26 | |
| Back on the Corner | John Hiatt | 3:52 | |
| Betty | Fred Eaglesmith | 2:17 | |
| Rotten Alabama | Ramsay Midwood | 3:51 | |
| Goodbye, Good-Lookin' | Robbie Fulks | 3:01 | |
| Take These Chains From My Heart | John Doe, The Sadies | 2:08 | |
| No Way I'll Never Need You | The Flatlanders | 3:17 | |
| Daddy's Little Pumpkin | Jeffrey Foucault | 2:32 | |
| I Am Your Tambourine | Tift Merritt | 3:44 | |
| Heart A Mine | Blackie & The Rodeo Kings, Mary Margaret O'Hara | 3:56 | |
| Valley Road | James McMurtry | 4:45 | |
| Keep Your Distance | Buddy & Julie Miller | 3:49 | |
| Boy From Oklahoma | Willis Alan Ramsey | 3:54 | |
| Jailhouse Tears | Lucinda Williams | 5:25 | |
| You Make My Heart Beat Too Fast | Buddy & Julie Miller | 3:12 | |
| Goodbye Old Missoula | Willis Alan Ramsey | 5:03 | |
