| Better Times Will Come | Diana Jones | 2:53 | |
| One Little Song | Gillian Welch | 3:13 | |
| Tecumseh Valley | Nanci Griffith | 4:29 | |
| Goodnight Irene | Kelly Joe Phelps | 5:39 | |
| The Oil Rigs at Night | The Delines | 4:23 | |
| Pneumonia alley | Elliott Murphy | 5:42 | |
| Venezuela | Dayna Kurtz | 4:55 | |
| Lay Me Down | Crosby & Nash | 3:36 | |
| Late For The Sky | Jackson Browne & David Lindley | 6:03 | |
| Rogers Park | Justin Townes Earle | 4:27 | |
| Wondering | Teddy Thompson, Kelly Jones | 2:38 | |
| Sweeten the Distance | Dori Freeman, Teddy Thompson | 5:12 | |
| The Highwayman (feat. Mark Knopfler) | Jimmy Webb, Mark Knopfler | 4:17 | |
| Our Town | Iris DeMent | 5:00 | |
| I Should Have Said | Bap Kennedy | 3:17 | |
| My Favorite Picture of You | Guy Clark | 3:32 | |
| A Whiter Shade of Pale | Dan Reeder | 3:36 | |
| Solitary Man | Tracy Grammer | 3:26 | |
| Say Grace | Sam Baker | 4:19 | |
| A Case of You | k.d. lang | 5:11 | |
| Hug You Like a Mountain - Radio Edit | Eliza Carthy, The Wayward Band, Teddy Thompson | 2:56 | |
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| Boots of Spanish Leather | Nanci Griffith | 6:13 | |
| Rumble Doll | Patti Scialfa | 3:25 | |
| To Ramona | Sinéad Lohan | 3:43 | |
| Everybody Knows | The Jayhawks | 4:10 | |
| It's Not Happening | The Be Good Tanyas | 2:41 | |
| Simple Gearle | Stacey Earle | 2:30 | |
| Unknown Legend | Caitlin Canty | 3:55 | |
| Everything Is Free | Gillian Welch | 4:47 | |
| You Took My Future | Teddy Thompson, Kelly Jones | 2:19 | |
| Draft Daughter's Blues aka Ootischenia | The Be Good Tanyas | 3:21 | |
| Only Fooling - Commentary | Kelly Jones, Teddy Thompson | 1:25 | |
| Arlington | The Wailin' Jennys | 4:54 | |
| It's a Dream | Neil Young | 6:29 | |
| A Love Song for Bobby Long | Grayson Capps | 4:53 | |
| Lonely Street | Bap Kennedy | 4:16 | |
| Killing the Blues | Chris Smither | 5:49 | |
| Don't Give Up (feat. Sinéad O'Connor) | Willie Nelson, Sinéad O'Connor | 6:58 | |
| Beyond the Shore | Willard Grant Conspiracy | 3:13 | |
| It's So Sweet | Jenni Muldaur, Teddy Thompson | 2:25 | |
| River Of Love | T Bone Burnett | 3:31 | |
| Once Were Brothers | Robbie Robertson | 4:24 | |
| Lights Of Taormina | Mark Knopfler | 6:09 | |
| I Miss You | Randy Newman | 3:55 | |
| Simple Twist Of Fate | Sarah Jarosz | 4:53 | |
| Brink Of Love | Teddy Thompson | 4:57 | |
| Anthem | Perla Batalla, Julie Christensen | 6:11 | |
| Silver Eagle | Mark Knopfler | 5:01 | |
| Change Of Heart | Teddy Thompson | 3:05 | |
