| Back In the High Life Again | Warren Zevon | 3:13 | |
| This Changes Everything | Jim Lauderdale | 3:32 | |
| Irene (Ravin' Bomb) | Ian Noe | 3:58 | |
| Mama Bake a Pie (Daddy Kill a Chicken) | Drive-By Truckers | 3:19 | |
| Dusty Bottles | Willie Nelson | 3:30 | |
| What of Alicia | Terry Allen | 5:03 | |
| Dirty Life and Times | Warren Zevon | 3:15 | |
| Dwight Yoakam | Sarah Shook & the Disarmers | 3:40 | |
| I'd Have to Be Crazy | Willie Nelson | 3:24 | |
| Not A Dry Eye In The House | Jeannie Seely, Willie Nelson | 3:47 | |
| I'll Let You Pick a Window | Barna Howard | 3:34 | |
| Take It Easy | Jackson Browne | 3:51 | |
| Highway 46 | Tom Russell | 4:05 | |
| Buffalo Return to the Plains | Jimmy LaFave | 4:08 | |
| Hurtin' (On the Bottle) | Margo Price | 4:12 | |
| No Time to Cry | Iris DeMent | 6:48 | |
| Everybody's Talkin' | Willie Nelson | 3:22 | |
| South | Blackie & The Rodeo Kings | 4:24 | |
| Midnight At the Movies | Justin Townes Earle | 3:22 | |
| Learning to Lose (feat. Willie Nelson) | Margo Price, Willie Nelson | 6:19 | |
| The Bottom of the World | Bottom of the World | 4:30 | |
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| Cigarettes And Wine | Jason Isbell and the 400 Unit | 6:42 | |
| Why You Been Gone So Long, Pt. 1 | Mickey Newbury | 3:28 | |
| Songbird | Eric Clapton, Willie Nelson | 2:55 | |
| Desperate & Depressed | Margo Price | 3:31 | |
| Green Mountains and Me | Slaid Cleaves | 3:44 | |
| I Gotta Get Drunk (with Willie Nelson) | George Jones | 2:10 | |
| Living on the Run | David Allan Coe | 2:32 | |
| This Forgotten Town | The Jayhawks | 3:46 | |
| Worrisome Years | Greg Brown | 4:08 | |
| Jesus Take the Wheel (and Drive Me to a Bar) | Sam Outlaw | 3:19 | |
| Fishin' with You | Carsie Blanton | 2:16 | |
| Pale Blue Eyes | Alejandro Escovedo | 6:15 | |
| Stay Young | Don Williams | 3:07 | |
| Darkness On The Face Of The Earth | Willie Nelson | 2:33 | |
| One Good Year | Slaid Cleaves | 4:26 | |
| Cosmic Cowboy, Pt. 1 | Michael Martin Murphey | 3:57 | |
| Tell Moses | Colvin & Earle | 3:41 | |
| Invisible Blue | Logan Ledger | 3:34 | |
| Trouble Over Me | Tift Merritt | 5:08 | |
| Sinner | Aaron Lewis, Willie Nelson | 3:31 | |
| Broke Down | Slaid Cleaves | 3:10 | |
| Goodbye Old Missoula | Willis Alan Ramsey | 5:03 | |
| These Lonely Nights | Willie Nelson | 3:29 | |
| Set Me Down On A Cloud | Lukas Nelson and Promise of the Real, Lucius | 7:16 | |
| Night Life | B.B. King, Willie Nelson | 4:32 | |
| $ 1000 Wedding | Willie Nelson | 3:04 | |
| Maria (Shut Up And Kiss Me) | Willie Nelson | 4:20 | |
| If I Started Over | Lukas Nelson and Promise of the Real | 3:12 | |
