| Whiskey Angel | The Black Lillies | 4:52 | ||
| Take it Out Back | Chuck Brodsky | 3:10 | ||
| My Sweet Annette | Drive-By Truckers | 3:51 | ||
| Shady Grove | Jerry Garcia, David Grisman | 4:19 | ||
| Lost On The Desert | Marty Stuart And His Fabulous Superlatives | 2:34 | ||
| Crossing Muddy Waters | John Hiatt | 4:05 | ||
| The Great Joe Bob (a Regional Tragedy) | Terry Allen | 4:42 | ||
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | ||
| Sixteen Angels Dancing 'Cross the Moon | Chip Taylor, John Prine | 3:18 | ||
| Ramblin' Kind | Jack Klatt | 2:51 | ||
| Samson And Delilah (feat. The Fairfield Four) | Willie Watson, The Fairfield Four | 3:03 | ||
| One Red Rose | Iris DeMent | 3:07 | ||
| Solving Problems | Brent Cobb | 2:34 | ||
| Mama Needs a Margarita | Zoe Muth | 4:06 | ||
| Down in My Hometown | The Flatlanders | 2:45 | ||
| Alabama Shamrock | Hackensaw Boys | 5:05 | ||
| Cortez Sail | Terry Allen | 6:10 | ||
| Devilsong | Shinyribs | 4:33 | ||
| Hard On You | Daniel Romano | 3:27 | ||
| Cigarette Machine | Fred Eaglesmith | 4:31 | ||
| Unwed Fathers | John Prine | 3:29 | ||
| Unlock more with Songs Like X Pro | ||||
| The Old Guard | Slaid Cleaves | 3:44 | ||
| Melinda Down the Line | Ian Fitzgerald | 5:06 | ||
| No More Crying The Blues | The Cactus Blossoms | 2:03 | ||
| Dublin Blues | Guy Clark | 4:19 | ||
| Still Fighting the War | Slaid Cleaves | 2:56 | ||
| Clocks and Spoons | John Prine | 3:14 | ||
| Self Destructive Zones | Drive-By Truckers | 4:12 | ||
| What It Takes | Fred Eaglesmith | 3:57 | ||
| Leave The Light On | Chris Smither | 3:47 | ||
| I Sang The Song | Mac Wiseman, John Prine, Peter Cooper, Thomm Jutz | 3:35 | ||
| Six Pack of Beer and a Pack of Cigarettes | Erik Koskinen | 3:59 | ||
| Livin' in the Woods in a Tree | Blaze Foley | 2:09 | ||
| Must Be the Whiskey | Chip Taylor, Carrie Rodriguez | 3:59 | ||
| I Just Lived a Country Song | Robbie Fulks, Linda Gail Lewis | 4:10 | ||
| Get A Better One | Chris Smither | 2:46 | ||
| Lisa's Birthday | Drive-By Truckers | 3:19 | ||
| Bear Creek Blues | John Prine | 4:45 | ||
| London Homesick Blues | Jerry Jeff Walker | 7:46 | ||
| Just Outside Of Austin | Lukas Nelson and Promise of the Real | 4:44 | ||
| Broke Down | Slaid Cleaves | 3:10 | ||
| Colorado | The Flying Burrito Brothers | 4:52 | ||
| Jaded Lover | Jerry Jeff Walker | 4:00 | ||
| Drunken Angel | Lucinda Williams | 3:20 | ||
| Two More Bottles Of Wine | Delbert McClinton | 3:01 | ||
| That's How I Got To Memphis | Tom T. Hall | 3:02 | ||
| Pissin' In The Wind | Jerry Jeff Walker | 4:00 | ||
| The Road Goes On Forever | Joe Ely | 4:33 | ||
| River Of Fools | Logan Ledger | 3:11 | ||
