| Helen's Restaurant | Daniel Romano | 2:43 | ||
| Way Out West | Marty Stuart And His Fabulous Superlatives | 5:41 | ||
| Appalachian Girl | Pert Near Sandstone | 4:18 | ||
| Ten Miles Down the Nine Mile Road | Scott Miller | 4:13 | ||
| Katie | Fred Eaglesmith | 3:42 | ||
| Mexican Cowboy | Willie Watson | 3:53 | ||
| One Road More | The Flatlanders | 2:38 | ||
| The Road Neverending | The Tillers | 4:01 | ||
| Cowboy Song | Dan Reeder | 2:35 | ||
| Angeline | James McMurtry | 4:04 | ||
| Story of You | The Flatlanders | 2:00 | ||
| Great American Roadside | Otis Gibbs | 2:49 | ||
| Milly's Café | Fred Eaglesmith | 5:28 | ||
| Wait A Minute | The Seldom Scene | 3:35 | ||
| Heavy | Possessed by Paul James | 4:35 | ||
| Coyotes Sing Tonight | Melissa Carper, Rebecca Patek | 2:38 | ||
| Shadow of the Moon | The Flatlanders | 2:52 | ||
| Cedarwood Pines | The Brothers Comatose | 3:52 | ||
| I'll Trade You Money for Wine | Robbie Fulks | 4:33 | ||
| The Plan | The Bones of J.R. Jones | 3:41 | ||
| Like You Used To | Watchhouse | 4:37 | ||
| Unlock more with Songs Like X Pro | ||||
| Alabama Shamrock | Hackensaw Boys | 5:05 | ||
| Hog of the Foresaken | Michael Hurley | 4:35 | ||
| 12 Bar Blues | Aaron Lee Tasjan | 5:04 | ||
| Who Woulda Thunk It | Greg Brown | 4:38 | ||
| Heart Over Mind - GemsOnVHS Field Recording | Todd Day Wait, GemsOnVHS | 2:22 | ||
| The Very Best | The Good Luck Thrift Store Outfit | 2:50 | ||
| The Midnight Special | Billy Bragg, Joe Henry | 3:34 | ||
| The Weekend | Dave Rawlings Machine | 5:29 | ||
| Mama | Lula Wiles | 3:18 | ||
| All over Now | Woody Pines | 3:05 | ||
| My Blinded Heart | Watchhouse | 4:47 | ||
| What of Alicia | Terry Allen | 5:03 | ||
| House of the White Rose Boquet | Ray Wylie Hubbard | 3:23 | ||
| Unwed Fathers (feat. Liz Isenberg) | Deer Tick, Liz Isenberg | 3:39 | ||
| Shoulda Been Done | Kieran Kane, Rayna Gellert | 2:10 | ||
| Humidifier | Jonny Fritz | 2:22 | ||
| Johnny Cash | Fred Eaglesmith | 3:20 | ||
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | ||
| I Wish We Had Our Time Again | Todd Snider | 2:28 | ||
| Irene (Ravin' Bomb) | Ian Noe | 3:58 | ||
| Randall Collins | Norman Blake | 1:55 | ||
| Spinnin' On This Rock | Ramsay Midwood | 4:30 | ||
| Boy From Oklahoma | Willis Alan Ramsey | 3:54 | ||
| I Feel The Blues Moving In | Slaid Cleaves | 4:08 | ||
| King Of California | Dave Alvin | 4:50 | ||
| Feed My Monkey | Ramsay Midwood | 3:18 | ||
| Girl Of The North Country | Sam Bush | 5:17 | ||
| Painted Lady | Willis Alan Ramsey | 3:06 | ||
