| Simple Gearle | Stacey Earle | 2:30 | |
| Infamous Angel | Iris DeMent | 3:46 | |
| Spring Wind | Greg Brown | 4:34 | |
| Gone by the Ol' Sunrise | Malcolm Holcombe, Iris DeMent | 3:00 | |
| Red Dog Tracks | Chip Taylor, Carrie Rodriguez | 4:47 | |
| Better Times Will Come | Diana Jones | 2:53 | |
| You Must Go | Lilly Hiatt | 5:02 | |
| When You Need a Train It Never Comes | Amanda Shires | 4:14 | |
| All The Lilacs In Ohio | John Hiatt, Jerry Douglas | 3:29 | |
| Your Lonely Heart | Carrie Rodriguez | 2:58 | |
| Mr. Bojangles | Jerry Jeff Walker | 5:28 | |
| Ford Econoline | Chuck Prophet | 3:41 | |
| Nothing Good Can Come from This | Amy Speace | 3:11 | |
| Heal Me | Sarah Shook & the Disarmers | 3:08 | |
| One Red Rose | Iris DeMent | 3:07 | |
| Isn't That So | Jesse Winchester | 2:25 | |
| Draft Daughter's Blues aka Ootischenia | The Be Good Tanyas | 3:21 | |
| Short Haired Woman Blues | Dave Rawlings Machine | 6:43 | |
| Till I'm Too Old to Die Young (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:29 | |
| I'll Take My Sorrow Straight | Iris DeMent | 3:27 | |
| New Damnation Alley | Malcolm Holcombe, Iris DeMent | 4:20 | |
| Unlock more with Songs Like X Pro |
| Here in California | Kate Wolf | 5:30 | |
| Worrisome Years | Greg Brown | 4:08 | |
| Jukebox | The Honeycutters | 4:36 | |
| We'll Sweep out the Ashes in the Morning - 2007 Remaster | Gram Parsons | 3:14 | |
| Must Be the Whiskey | Chip Taylor, Carrie Rodriguez | 3:59 | |
| Drunken Barber's Hand | Slaid Cleaves | 2:41 | |
| Pretty Girl | Diana Jones | 3:10 | |
| Goodnight Rhonda Lee | Nicole Atkins | 2:33 | |
| Mr. Bojangles | David Bromberg | 7:28 | |
| Two Different Things | Caitlin Cary, Thad Cockrell | 4:16 | |
| Powderfinger | Cowboy Junkies | 5:45 | |
| Mississippi You're On My Mind | Jesse Winchester | 3:26 | |
| Birthday Song | Amanda Anne Platt & the Honeycutters | 4:15 | |
| Adios to California | John Hiatt | 3:47 | |
| East of Eden | Tom Rush | 3:29 | |
| From an Airplane | Iris DeMent | 2:45 | |
| Willin' | Richard Shindell | 3:15 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Next Door Down | Stacey Earle | 4:35 | |
| Mr. & Mrs. Used to Be (feat. Iris DeMent) | John Prine, Iris DeMent | 2:36 | |
| Flycatcher Jack and the Whippoorwill's Song (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 4:01 | |
| That's All It Took - 2002 Remaster | Gram Parsons | 3:01 | |
| Red Dirt Girl | Emmylou Harris | 4:05 | |
| That's What Makes You Strong | Jesse Winchester | 3:10 | |
| Mama's Opry | Nitty Gritty Dirt Band, Iris DeMent | 4:23 | |
| One Good Year | Slaid Cleaves | 4:26 | |
| I Am Your Tambourine | Tift Merritt | 3:44 | |
| Heart A Mine | Blackie & The Rodeo Kings, Mary Margaret O'Hara | 3:56 | |
