| Silver Lining | Carl Anderson | 2:30 | |
| Lindsey Button | David Rawlings | 5:03 | |
| Birthday Song | Amanda Anne Platt & the Honeycutters | 4:15 | |
| Station Blues | Pieta Brown, Chad Cromwell | 3:14 | |
| The Asp and the Albatross | Freakwater | 3:10 | |
| Battlechain Rose | Nicki Bluhm | 3:40 | |
| Still Fighting the War | Slaid Cleaves | 2:56 | |
| Another Black Hole | Malcolm Holcombe, Futureman, Tony Joe White | 4:23 | |
| My List | Shelby Lynne, Allison Moorer | 2:52 | |
| Your Sweet and Shiny Eyes - 2008 Remaster | Bonnie Raitt | 2:47 | |
| Oh Soul | Mary Gauthier | 5:26 | |
| The Road | Amanda Anne Platt & the Honeycutters | 2:39 | |
| Calm Before the Storm | Eliza Gilkyson | 3:50 | |
| All the Way to Amsterdam | Greg Trooper | 2:59 | |
| How's About You | Dave Rawlings Machine | 3:54 | |
| House of the White Rose Boquet | Ray Wylie Hubbard | 3:23 | |
| Let the Mystery Be | Iris DeMent | 2:50 | |
| Trouble Looks Good on You | Amy Speace | 2:52 | |
| Nobody Wants to Be You | Dan Reeder | 2:08 | |
| Pilgrim (You Can't Go Home) | Dave Rawlings Machine | 7:57 | |
| Unknown Legend | Caitlin Canty | 3:55 | |
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| Sorrow Be the Bird | Lula Wiles | 3:08 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Heart of America | Margo Price | 3:16 | |
| You're Still On My Mind | Carrie Rodriguez | 2:56 | |
| On the Ropes | The Honeycutters | 3:15 | |
| You Are My Home | Amanda Shires | 3:39 | |
| Don't Speak in English | Chip Taylor, Carrie Rodriguez | 4:01 | |
| It Was a Train | Otis Gibbs | 3:10 | |
| Got Your Six | Mary Gauthier | 2:38 | |
| Basil Gone to Blossom | Caitlin Canty | 3:07 | |
| E.N.S.A.A.T. | Aaron Lee Tasjan | 4:19 | |
| King Cotton | The Secret Sisters | 3:12 | |
| Forever and Then Some | Lillie Mae | 4:49 | |
| Dallas | The Flatlanders | 3:01 | |
| Willin' | Richard Shindell | 3:15 | |
| Lonesome Old River Blues | Dom Flemons | 2:42 | |
| One Good Year | Slaid Cleaves | 4:26 | |
| 8 Gods Of Harlem | Rosanne Cash, Elvis Costello, Kris Kristofferson | 3:54 | |
| It Was Always So Easy (To Find An Unhappy Woman) | Peter Wolf | 2:40 | |
| Just Say She's A Rhymer | Mary Gauthier | 4:17 | |
| Long As I Can See The Light | Ted Hawkins | 3:13 | |
| Crocodile Man | Chris Smither | 3:33 | |
| Wildflowers | Chris Hillman | 2:51 | |
| Before You Leave | Mary Gauthier | 3:42 | |
| The River's Gonna Run | Buddy & Julie Miller | 3:59 | |
| Oh, Sister [Feat. Courtney Marie Andrews] | Logan Ledger, Courtney Marie Andrews | 3:40 | |
| Farewell Angelina | Tim O'Brien | 4:23 | |
| Flowered Dresses | Slaid Cleaves | 3:49 | |