| Don't You Wanna Know | Gráinne Duffy | 3:25 | |
| Livingston | Mary Chapin Carpenter | 5:13 | |
| Train Home | Chris Smither | 4:25 | |
| Shame on the Moon | Rodney Crowell | 4:40 | |
| Sea Fever (feat. Mark Knopfler) | William Topley | 4:35 | |
| The Sea & the Shore (feat. John Fullbright) | Amy Speace, John Fullbright | 4:14 | |
| Somewhere in the Middle (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 2:41 | |
| Still Learning How to Fly | Rodney Crowell | 4:12 | |
| Speed of the Sound of Loneliness | Nanci Griffith | 4:20 | |
| Something Smooth | Pete Alderton | 4:15 | |
| Different World | Guy Fletcher, Mark Knopfler | 4:42 | |
| There In Your Heart | Beth Hart | 4:31 | |
| Think About You | Eliza Gilkyson | 3:23 | |
| Whistle on Occasion (feat. Chuck Prophet) | Kim Richey, Chuck Prophet | 2:36 | |
| Desert Dove | Michaela Anne | 4:41 | |
| Coyotes Are Howlin' | Joe Ely | 4:18 | |
| Making Lovers Out Of Friends | Rodney Crowell | 4:30 | |
| Boots of Spanish Leather | Nanci Griffith | 6:13 | |
| Millionaire | Kevin Welch | 3:59 | |
| Shotgun Hearts | Amy Speace, The Orphan Brigade | 4:46 | |
| Time Stands Still | Chris Smither | 3:45 | |
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| Picture (feat. Sheryl Crow) | Kid Rock, Sheryl Crow | 4:58 | |
| Is It Like Today | Eliza Gilkyson | 5:49 | |
| When My Morning Comes Around | Iris DeMent | 3:51 | |
| Long As I Can See The Light | Shemekia Copeland | 3:21 | |
| King of Mexico | Bap Kennedy | 3:29 | |
| Wear Me Out | Jesse Winchester | 2:37 | |
| Jukebox | The Honeycutters | 4:36 | |
| Oh Set a Light | Chip Taylor, Carrie Rodriguez | 3:44 | |
| My Favorite Picture of You | Guy Clark | 3:32 | |
| Tell Me Anything (Turn to Gold) | Chuck Prophet | 3:22 | |
| River Girl | Kelley Mickwee | 4:47 | |
| Clean Getaway | Kieran Kane, Kevin Welch, Fats Kaplin | 2:50 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| If I Had a Heart | Slaid Cleaves | 3:46 | |
| The Road Goes On Forever | Joe Ely | 4:33 | |
| St. Olav's Gate | Tom Russell, Nanci Griffith | 3:10 | |
| Love Without You | Darius Rucker, Sheryl Crow | 3:19 | |
| Morning Is My Destination | Tift Merritt | 3:17 | |
| No Souvenirs | Melissa Etheridge | 4:34 | |
| Silver Eagle | Mark Knopfler | 5:01 | |
| Soap Box Preacher | Robbie Robertson | 5:20 | |
| Blue | Zucchero, Sheryl Crow | 4:48 | |
| I Am Your Tambourine | Tift Merritt | 3:44 | |
| Tonight Will Be Fine | Teddy Thompson | 3:36 | |
| If It Makes You Happy | Sheryl Crow | 5:23 | |
| Sometimes We Cry | Shana Morrison | 4:42 | |
| I Wish It Would Rain | Rodney Crowell | 3:28 | |
| Hold Steady / Rock Slow | Birds of Chicago | 5:15 | |