| Down on Penny's Farm | Natalie Merchant | 3:43 | |
| Lint Head Gal | Phoebe Hunt, The Gatherers | 2:49 | |
| Oh Set a Light | Chip Taylor, Carrie Rodriguez | 3:44 | |
| Leaping Out | Caitlin Canty | 3:55 | |
| Terms of My Surrender | John Hiatt | 3:29 | |
| Different When It Comes To You | Bruce Cockburn | 2:57 | |
| Hearts Beat and Take a Beating | Forest Sun | 3:16 | |
| New York | Amanda Anne Platt & the Honeycutters | 4:17 | |
| You Got to Me | James McMurtry | 5:23 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Shirt | Peter Mulvey | 3:32 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Black Mountain Lullaby | Caroline Herring | 4:11 | |
| Old Friends | Chuck Prophet | 3:56 | |
| Wide Open Plain | Doug Paisley | 5:34 | |
| Flycatcher Jack and the Whippoorwill's Song (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 4:01 | |
| South | Blackie & The Rodeo Kings | 4:24 | |
| Promises to Keep | Eliza Gilkyson | 4:23 | |
| Red Pony | Dead Horses | 3:53 | |
| The Sea & the Shore (feat. John Fullbright) | Amy Speace, John Fullbright | 4:14 | |
| Hard Bargain | Ron Sexsmith | 3:12 | |
| Unlock more with Songs Like X Pro |
| Pacing The Cage | Bruce Cockburn | 4:40 | |
| I Don't Know Why | Kieran Kane, Rayna Gellert | 3:09 | |
| Unknown Legend | Caitlin Canty | 3:55 | |
| Little Rain | Hiss Golden Messenger | 3:52 | |
| The Road | Amanda Anne Platt & the Honeycutters | 2:39 | |
| Borderline | Eliza Gilkyson | 2:42 | |
| Sweet Spot | Tift Merritt | 2:50 | |
| Guilty As a Saint | Chuck Prophet | 3:52 | |
| Bury Me Under the Weeping Willow | Natalie Merchant | 3:20 | |
| River Girl | Kelley Mickwee | 4:47 | |
| Canola Fields | James McMurtry | 4:49 | |
| Boulevard Of Broken Dreams | Bill Bourne | 3:25 | |
| Learning How to Love Him | Amanda Anne Platt & the Honeycutters | 4:16 | |
| Irene Wilde | Alejandro Escovedo | 2:51 | |
| Lost John Dean | Kieran Kane, Kevin Welch, Fats Kaplin | 3:26 | |
| Willie and Nilli | Chuck Prophet | 3:48 | |
| Melinda Down the Line | Ian Fitzgerald | 5:06 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Quite a Feelin' | Barna Howard | 4:09 | |
| Graveyard Fields | The Dead Tongues | 3:45 | |
| Killer | Jenifer McKitrick, Chuck Prophet, Katharine Cole, Stephanie Lee, Todd Duda | 5:01 | |
| Never Been a Captain | The Barr Brothers | 4:41 | |
| Can't Lose Them All | Kim Richey | 3:39 | |
| A Feather's Not A Bird | Rosanne Cash | 3:18 | |
| Fading | Kim Richey | 4:44 | |
| In State | Kathleen Edwards | 3:56 | |
| Good | Kim Richey | 3:27 | |
| Lay It Down | Kim Richey | 4:14 | |
