| $13 Beers | Chicago Farmer | 3:17 | |
| Cigarette Trees | The Local Honeys | 2:43 | |
| Misery and Gin | Jaime Wyatt | 4:24 | |
| Fuck This Town | Robbie Fulks | 2:24 | |
| Parting Words | Sarah Shook & the Disarmers | 3:15 | |
| Mississippi Goddam (feat. Adia Victoria & Kyshona Armstrong) | Kelsey Waldon, Adia Victoria, Kyshona | 4:54 | |
| Silver & Gold | Sam Doores, Riley Downing, The Tumbleweeds | 2:22 | |
| Saving Myself for Jesus | Birdcloud | 2:22 | |
| If I Can't Trust You with a Quarter (How Can I Trust You with My Heart?) | Zoe Muth and the Lost High Rollers | 5:07 | |
| That River | Margo Cilker | 3:09 | |
| South Dakota Wild One | The Deslondes, Riley Downing | 3:23 | |
| Carole With An E | Brennen Leigh | 3:35 | |
| Learning to Lose (feat. Willie Nelson) | Margo Price, Willie Nelson | 6:19 | |
| Johnny Cash | Fred Eaglesmith | 3:20 | |
| Chino | Kassi Valazza | 6:08 | |
| Kentucky, 1988 | Kelsey Waldon | 4:04 | |
| Don't Wanna Cry | Emily Nenni | 2:26 | |
| No More Crying The Blues | The Cactus Blossoms | 2:03 | |
| Sunday Sun | Garrett T. Capps | 3:46 | |
| Trust Jesus | Slobberbone | 4:14 | |
| Sinkhole | Drive-By Truckers | 3:27 | |
| Unlock more with Songs Like X Pro |
| I Remember Carolina | Margo Cilker | 4:54 | |
| Hell's Canyon | Lost Dog Street Band | 5:41 | |
| Howard Hughes Blues | Robert Ellis, Courtney Hartman | 2:50 | |
| Won't Fence Us In | Nick Shoulders | 2:34 | |
| Trinity Lane | Lilly Hiatt | 3:53 | |
| Stoplight Kisses | The Cactus Blossoms | 2:17 | |
| Shooter | Angela Autumn | 4:15 | |
| King Cotton | The Secret Sisters | 3:12 | |
| What It Takes - Audiotree Live Version | Sarah Shook & the Disarmers, Audiotree | 2:59 | |
| Less Honkin' More Tonkin' | The Deslondes, Riley Downing | 1:42 | |
| My Sweet Annette | Drive-By Truckers | 3:51 | |
| Take 'Em Away | Old Crow Medicine Show | 3:34 | |
| Trouble | Sophie Gault, Logan Ledger | 3:47 | |
| Fuck Me Up | Pokey LaFarge | 3:40 | |
| Jars At Home | Trampled by Turtles | 2:09 | |
| Paper Cowboy | Margo Price | 6:15 | |
| Laugh to Keep from Crying | Emily Nenni | 3:44 | |
| Welcome to Hard Times | Charley Crockett | 3:05 | |
| I Wont Let You Down - GemsOnVHS Field Recording | Josh Okeefe, Cora Carpenter, GemsOnVHS | 2:38 | |
| Daddy's Cup | Drive-By Truckers | 5:53 | |
| Can't Stay Long | Scott H. Biram | 3:18 | |
| (This Ain't A) Sad Song | The Deslondes, Sam Doores | 3:21 | |
| Tennessee Song | Margo Price | 4:40 | |
| Lesson | Sarah Shook & the Disarmers | 2:45 | |
| Nobody Gives a Damn About Songs Anymore | John Moreland | 3:15 | |
| All Blue | Luke Bell | 3:21 | |
| Playground / Battlefield | Joseph Huber | 4:20 | |
| Monster Truck | Ramsay Midwood | 3:30 | |
