| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| Omaha | The Gourds | 3:15 | |
| Wilder Than Her | Fred Eaglesmith | 4:54 | |
| Sadder Day | Western Centuries | 4:30 | |
| Whiskey Angel | The Black Lillies | 4:52 | |
| Devilsong | Shinyribs | 4:33 | |
| Oh Julia | John Moreland | 3:47 | |
| Hard Livin' | Justin Townes Earle | 2:48 | |
| Please, Please, Please | Andrew Combs | 4:27 | |
| Drivin' | Robert Ellis | 2:46 | |
| Homeless (feat. Michael Rose) | Parker Millsap, Michael Rose | 3:12 | |
| Long Wide Open Road | Darrell Scott | 5:01 | |
| Cowboy Song | Dan Reeder | 2:35 | |
| The Weekend | Dave Rawlings Machine | 5:29 | |
| Just Someone I Used To Know | Buddy Miller, Nikki Lane | 2:22 | |
| I've Been Gone | Zoe Muth and the Lost High Rollers | 4:28 | |
| Ain't Glad I'm Leaving | Justin Townes Earle | 2:32 | |
| Wrong Way to Run | Willy Tea Taylor | 2:34 | |
| Dead on the River (Rolling Down) | Ian Noe | 5:06 | |
| Mexican Cowboy | Willie Watson | 3:53 | |
| If I Cant Win | The Cactus Blossoms | 3:17 | |
| Unlock more with Songs Like X Pro |
| Fuck Up | Sarah Shook & the Disarmers | 3:21 | |
| Turtle Dove & the Crow | Watchhouse | 3:22 | |
| Keweenaw Flower | The Lowest Pair | 3:23 | |
| For Sam | Willy Tea Taylor, The River Arkansas | 4:39 | |
| Hotter Than Mojave in My Heart | Iris DeMent | 2:33 | |
| Tired of Everything | Yarn | 3:31 | |
| Love Will Only Break Your Heart | The David Mayfield Parade | 2:53 | |
| Sweet Daffodil | The Hill Country Devil | 2:27 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Blue Canoe | Blue Mountain | 4:39 | |
| Learning to Lose (feat. Willie Nelson) | Margo Price, Willie Nelson | 6:19 | |
| My Old Drunk Friend | Freakwater | 3:33 | |
| Detroit or Buffalo | Amanda Shires | 4:08 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
| Wait A Minute | The Seldom Scene | 3:35 | |
| Old Blue Dog | Charlie Parr | 5:21 | |
| Silhouette | Dave Simonett | 2:58 | |
| Tres Grand Serpent | The Deslondes, Riley Downing | 2:40 | |
| Blue and Wonder | Richard Buckner | 3:47 | |
| Off This Mountaintop | Ian Noe | 3:32 | |
| Keep It Clean | Willie Watson | 3:35 | |
| Lullaby | Willy Tea Taylor | 3:27 | |
| Hey Stranger | Watchhouse | 3:27 | |
| Worrisome Years | Greg Brown | 4:08 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Fear of Trains | William Elliott Whitmore | 4:00 | |
| I Wish It Would Rain | Rodney Crowell | 3:28 | |
| The Mountain | Levon Helm | 3:35 | |
