| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Old Shoes | Tom Waits | 4:25 | |
| Mexican Cowboy | Willie Watson | 3:53 | |
| Now It's Now Again | The Flatlanders | 3:33 | |
| You're Dreaming | The Cactus Blossoms | 3:25 | |
| Sitting On Top Of the World | Doc Watson | 3:45 | |
| I Sang The Song | Mac Wiseman, John Prine, Peter Cooper, Thomm Jutz | 3:35 | |
| How Lucky | John Prine | 3:38 | |
| My Bucket's Got a Hole in It | Chip Taylor, Carrie Rodriguez | 2:32 | |
| It Ain't Over Yet | Rodney Crowell, Rosanne Cash, John Paul White | 5:14 | |
| Keep It Clean | Willie Watson | 3:35 | |
| Story of You | The Flatlanders | 2:00 | |
| Looking at the World Through a Windshield | Son Volt | 3:08 | |
| My Mind's Got a Mind of Its Own | Jimmie Dale Gilmore | 2:31 | |
| Memories | Swamp Dogg, John Prine | 4:47 | |
| Just Us Kids | James McMurtry | 5:08 | |
| Codeine | Jason Isbell and the 400 Unit | 5:44 | |
| Mama Bake a Pie (Daddy Kill a Chicken) | Drive-By Truckers | 3:19 | |
| Downtown Tonight | John Gorka | 3:05 | |
| Willin' | Little Feat | 2:54 | |
| Return Into Dust | Gordon Lightfoot | 3:09 | |
| Unlock more with Songs Like X Pro |
| Ain't Got a Place | James McMurtry | 2:41 | |
| Death of the Last Stripper | Terry Allen, The Panhandle Mystery Band | 3:19 | |
| Golden Embers | Watchhouse | 4:45 | |
| If You Were The Woman And I Was The Man | Cowboy Junkies, John Prine | 3:14 | |
| Yes I Guess They Oughta Name a Drink After You | John Prine | 2:10 | |
| No Depression | Uncle Tupelo | 2:20 | |
| The Man Who Couldn't Cry | Loudon Wainwright III | 6:15 | |
| Shadow of the Moon | The Flatlanders | 2:52 | |
| Draft Daughter's Blues aka Ootischenia | The Be Good Tanyas | 3:21 | |
| One's On The Way (feat. Margo Price) | Loretta Lynn, Margo Price | 2:41 | |
| Oh Soul | Mary Gauthier | 5:26 | |
| Keep 'Em on They Toes | Brent Cobb | 2:43 | |
| Play a Train Song | Todd Snider | 4:09 | |
| Walking Down the Line | Eilen Jewell | 3:37 | |
| Song For A Deck Hands Daughter | James McMurtry | 3:30 | |
| Mexican Home (feat. John Prine) | Chris Knight, John Prine | 5:05 | |
| Desperado | The Cactus Blossoms | 2:46 | |
| Captain's Song (Sorley Boy) | The Orphan Brigade, John Prine | 3:11 | |
| Something To Love | Jason Isbell and the 400 Unit | 3:39 | |
| Me and Bobby McGee | Gordon Lightfoot | 3:46 | |
| Fishing With Bill | Bill Morrissey, Greg Brown | 4:32 | |
| I Drink | Mary Gauthier | 4:30 | |
| Goodbye Old Missoula | Willis Alan Ramsey | 5:03 | |
| Where Have All The Average People Gone - Single Version | Roger Miller | 3:01 | |
| The River Knows Your Name | John Hiatt | 4:25 | |
| She's That Kind Of Mystery | Bill Morrissey | 3:29 | |
| Guadalupe | Tom Russell | 6:04 | |
| You Were On My Mind | Colvin & Earle | 2:56 | |
