| Dream Café | Greg Brown | 5:57 | |
| Daisy Mae | Jason Isbell and the 400 Unit | 2:55 | |
| Winsome Smile | Chris Smither | 3:34 | |
| Outskirts | James McMurtry | 4:07 | |
| My Old Drunk Friend | Freakwater | 3:33 | |
| The Poet Game | Greg Brown | 5:32 | |
| Coast | Eliza Gilkyson | 3:25 | |
| Wasted and Rollin' | Amanda Shires | 3:52 | |
| Poor Girl - Klein | Po' Girl | 3:10 | |
| Green Mountains and Me | Slaid Cleaves | 3:44 | |
| Dancing To The Rhythm Of Rain (feat. Tift Merritt) | Reto Burrell, Tift Merritt | 4:24 | |
| Mercy | Po' Girl | 4:56 | |
| I Shall Weep at Night | Brad Mehldau, Simone Dinnerstein, Tift Merritt | 4:49 | |
| Hundred Dollar Valentine | Chris Smither | 3:05 | |
| Life Is Bad | Shelby Lynne | 3:18 | |
| Something Less Than Something More | Caitlin Cary, Thad Cockrell | 5:08 | |
| Play a Train Song | Todd Snider | 4:09 | |
| Maiden Voyage | Caroline Herring | 3:41 | |
| Mississippi You're On My Mind | Jesse Winchester | 3:26 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Be With You | Pieta Brown | 2:27 | |
| Unlock more with Songs Like X Pro |
| Wichita Ain't so Far Away | The Delines | 2:31 | |
| Simple Gearle | Stacey Earle | 2:30 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Pass You By | Gillian Welch | 3:57 | |
| Sin City - 2007 Remaster | Beck & Emmylou Harris | 4:00 | |
| Calm Before the Storm | Eliza Gilkyson | 3:50 | |
| Don't You Fall | The Be Good Tanyas | 3:38 | |
| Sure Feels Good Anyway | Amy Ray | 4:30 | |
| After the Storm | The Flatlanders | 3:52 | |
| Prairie Girl Gone | Po' Girl | 6:21 | |
| Rex's Blues | Son Volt - Jay Farrar & Kelly Willis | 4:40 | |
| Better Times Will Come | Diana Jones | 2:53 | |
| Sweet Tequila Blues | Chip Taylor, Carrie Rodriguez | 3:15 | |
| Childish Things | James McMurtry | 4:35 | |
| Lebanon, Tennessee | Ron Sexsmith | 2:57 | |
| I'm Alright | Kim Richey | 4:01 | |
| Restless - Remastered | Alison Krauss & Union Station | 2:51 | |
| I Wish It Would Rain | Rodney Crowell | 3:28 | |
| Mixtape | Tift Merritt | 3:18 | |
| Leaving London | Puss N Boots | 3:08 | |
| Heart A Mine | Blackie & The Rodeo Kings, Mary Margaret O'Hara | 3:56 | |
| Little Darlin' | Buddy & Julie Miller | 3:31 | |
| When Will You Come Back Home | Ryan Adams & The Cardinals | 4:52 | |
| Tenessee Stud | The Little Willies | 3:49 | |
| The Things That Everybody Does | Tift Merritt | 3:05 | |
| Bottom Of The World | Alejandro Escovedo | 3:04 | |
| If The Law Don't Want You | Rodney Crowell, Mary Karr, Norah Jones | 2:51 | |
| You Can't Fail Me Now | Loudon Wainwright III | 3:45 | |
