| Pilgrim (You Can't Go Home) | Dave Rawlings Machine | 7:57 | |
| One of These Days | Bedouine | 2:58 | |
| Late Bloomer | The Secret Sisters | 4:20 | |
| Done | Frazey Ford | 4:41 | |
| Moonshiner | Uncle Tupelo | 4:23 | |
| Learning to Lose (feat. Willie Nelson) | Margo Price, Willie Nelson | 6:19 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| Swimming Song | Kate & Anna McGarrigle | 2:29 | |
| A Case of You | Joni Mitchell | 4:23 | |
| Give That Man A Road | Gillian Welch | 2:44 | |
| Wondering How | Pieta Brown | 3:06 | |
| Bonny Light Horseman | Bonny Light Horseman, Eric D. Johnson, Josh Kaufman, Anaïs Mitchell | 4:30 | |
| I Hear Them All | Dave Rawlings Machine | 2:27 | |
| Hallelujah (I’m a Dreamer) | Luther Dickinson, Amy LaVere | 2:48 | |
| Speed of the Sound of Loneliness | Kurt Vile | 5:15 | |
| Dark Eyes | Dawn Landes, Bonnie "Prince" Billy | 4:42 | |
| Picasso | Gillian Welch | 3:41 | |
| The Swimming Song | Loudon Wainwright III | 2:27 | |
| Don't Look for Me | Jeffrey Foucault | 3:05 | |
| Here in California | Kate Wolf | 5:30 | |
| Red & White & Blue & Gold | Aoife O'Donovan | 3:20 | |
| Unlock more with Songs Like X Pro |
| The Mother | Brandi Carlile | 3:16 | |
| Hello Sunshine | Damien Jurado, Richard Swift | 3:04 | |
| Remembering Mountains | Sharon Van Etten | 3:36 | |
| It Ain't Over Yet | Rodney Crowell, Rosanne Cash, John Paul White | 5:14 | |
| Our Town | Iris DeMent | 5:00 | |
| Bodysnatchers | Dave Rawlings Machine | 5:56 | |
| Havana Burning | Dan Reeder | 2:39 | |
| Big Cheeseburgers & Good French Fries | Blaze Foley | 2:14 | |
| 16, Maybe Less | Calexico, Iron & Wine | 4:49 | |
| I Wonder Why | Kacy & Clayton, Marlon Williams | 2:05 | |
| Boots of Spanish Leather | Nanci Griffith | 6:13 | |
| Valley Of Tears | Gillian Welch | 3:15 | |
| Conversation with Death | Brooke Buckner, George Buckner, David Rawlings, Gillian Welch | 6:16 | |
| Leave The Light On | Chris Smither | 3:47 | |
| Gonna Be Leaving | Abigail Lapell | 3:10 | |
| Hey Stranger | Watchhouse | 3:27 | |
| Across the Great Divide | Nanci Griffith | 3:57 | |
| Mining For Gold | Cowboy Junkies | 1:32 | |
| Persephone | Allison Russell | 4:22 | |
| Through the Morning, Through the Night | Robert Plant, Alison Krauss | 4:00 | |
| Fly High | Jay Farrar, Will Johnson, Anders Parker, Yim Yames | 3:45 | |
| May You Never | John Martyn | 3:40 | |
| Doin' What I Did | THe BAcksliders, Rhonda Vincent, Gillian Welch, Sara Evans, Bonnie Bramlett, The Blazers, Pete Drodge | 3:26 | |
| Danny’s Song | Tift Merritt | 2:08 | |
| The Maker | Willie Nelson | 5:08 | |
| Drifters Wife | J.J. Cale | 1:40 | |
| Who Knows Where The Time Goes? | Fairport Convention | 5:09 | |
| It Hurts Me Too | Karen Dalton | 3:07 | |
