| Crayon Angels | Judee Sill | 2:45 | |
| Gravity of the Situation | Vic Chesnutt | 4:09 | |
| After You're Gone | Iris DeMent | 4:04 | |
| The Pearl | Emmylou Harris | 5:00 | |
| Failed Christian | Nick Lowe | 3:56 | |
| Small Plane | Bill Callahan | 3:56 | |
| Feeling of Beauty | Tift Merritt | 4:01 | |
| Fair Play | Van Morrison | 6:14 | |
| Shipbuilding | The Unthanks | 3:46 | |
| If I Had a Gun | Diana Jones | 3:41 | |
| Railroad Man | Eels | 4:16 | |
| Souvenirs | John Prine | 3:42 | |
| Naked Souls | Bill Callahan | 9:45 | |
| House Carpenter | Natalie Merchant | 6:00 | |
| Blue and Wonder | Richard Buckner | 3:47 | |
| Boulder to Birmingham - 2003 Remaster | Emmylou Harris | 3:33 | |
| Northstar Blues | Magnolia Electric Co., Jason Molina | 5:08 | |
| Steve McQueen | Lambchop | 4:32 | |
| See My Love | Headless Heroes | 3:50 | |
| Red Dirt Girl | Emmylou Harris | 4:16 | |
| Used Cars | Bruce Springsteen | 3:08 | |
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| Where Will I Be | Emmylou Harris | 4:15 | |
| Our Town | Iris DeMent | 5:00 | |
| Shelter from the Storm | Rodney Crowell, Emmylou Harris | 5:26 | |
| Lately I've Let Things Slide | Nick Lowe | 3:06 | |
| Song for Adam - Remastered | Jackson Browne | 5:23 | |
| On the Road to Fairfax County | The Roches | 4:46 | |
| Cheap Hotel | Ron Sexsmith | 2:18 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| Fire in the Blood / Snake Song (feat. Emmylou Harris, feat. Ralph Stanley) | The Bootleggers, Emmylou Harris, Ralph Stanley | 4:25 | |
| Love Has No Pride - 2008 Remaster | Bonnie Raitt | 3:48 | |
| Hotter Than Mojave in My Heart | Iris DeMent | 2:33 | |
| The Road | Emmylou Harris | 5:28 | |
| Flirted With You All My Life | Vic Chesnutt | 4:41 | |
| Every Little Thing | T Bone Burnett | 2:52 | |
| Drifter's Escape | Patti Smith | 3:20 | |
| Frank's Tavern | Calexico | 4:28 | |
| Pontiac | Lyle Lovett | 2:25 | |
| Streets of Arklow | Van Morrison | 4:22 | |
| Killing the Blues | Robert Plant, Alison Krauss | 4:15 | |
| Lil' Wallet Picture | Richard Buckner | 4:32 | |
| Pretty Little Cemetery | Ron Sexsmith | 2:32 | |
| The Great Valerio | Richard & Linda Thompson | 5:26 | |
| Donkey Town | Mark Knopfler, Emmylou Harris | 5:42 | |
| Summer Blowin' Town | Ron Sexsmith | 2:18 | |
| The Ballad Of Easy Rider | Fairport Convention | 4:55 | |
| I'll Regret It All In The Morning | Richard & Linda Thompson | 3:36 | |
| For Shame Of Doing Wrong | Richard & Linda Thompson | 4:44 | |
| Speedway At Nazareth - Live At Gibson Amphitheatre / June 28th 2006 | Mark Knopfler, Emmylou Harris | 6:59 | |