| Take Home Pay | Slaid Cleaves | 2:51 | ||
| Fifty Miles of Elbow Room (Featuring Gillian Welch) | James Alan Shelton | 3:31 | ||
| Westbound Train | Robert Ellis | 4:07 | ||
| Sally Ann | Wild Ponies | 2:59 | ||
| Goodbye Summer | Jonny Fritz | 3:30 | ||
| Bluebird Wine | Rodney Crowell | 4:11 | ||
| Wasteland | Dead Man Winter | 4:42 | ||
| Wayside / Back in Time | Gillian Welch | 3:28 | ||
| Old Shoes | Tom Waits | 4:25 | ||
| I Got You (At the End of the Century) | Chatham County Line | 2:44 | ||
| Your Sweet and Shiny Eyes - 2008 Remaster | Bonnie Raitt | 2:47 | ||
| All The Lilacs In Ohio | John Hiatt, Jerry Douglas | 3:29 | ||
| Bells Of Harlem | Dave Rawlings Machine | 4:07 | ||
| Boxcar | Shovels & Rope | 4:41 | ||
| Got Your Six | Mary Gauthier | 2:38 | ||
| Kansas | Fred Eaglesmith | 3:44 | ||
| The One to Save | Trampled by Turtles | 4:27 | ||
| The Cuckoo Bird | Willie Watson | 3:12 | ||
| Swing Me Down | Danny Schmidt | 3:55 | ||
| Perfect Timing | Drive-By Truckers | 2:57 | ||
| You Can't Save Everybody (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:12 | ||
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| Adios Maria | The Cactus Blossoms | 4:09 | ||
| Ruby | Dave Rawlings Machine | 4:54 | ||
| Black T-Shirt | Slaid Cleaves | 3:14 | ||
| One for the One | John Hiatt | 4:18 | ||
| Shanty Boat | The Tillers | 4:17 | ||
| New Orleans | Dead Man Winter | 4:09 | ||
| Six White Horses | Gillian Welch | 3:38 | ||
| Cartoon Gold | Drive-By Truckers | 3:15 | ||
| Green Mountains and Me | Slaid Cleaves | 3:44 | ||
| Nashville 1972 | Rodney Crowell | 3:53 | ||
| Dusty Old Man | Tift Merritt | 3:47 | ||
| Here in the Kitchen | Dan Reeder | 1:28 | ||
| The Way It Dimmed | Amanda Shires | 2:11 | ||
| When A Cowboy Trades His Spurs For Wings | Gillian Welch, David Rawlings | 3:03 | ||
| Honky Tonks and Taverns | Lillie Mae | 2:19 | ||
| Goodbye My Son | The Good Luck Thrift Store Outfit | 3:25 | ||
| Lonesome Old River Blues | Dom Flemons | 2:42 | ||
| Only the Song Survives | John Hiatt | 4:00 | ||
| It's Too Easy | Dave Rawlings Machine | 3:08 | ||
| Back in My Day Blues | Otis Gibbs | 3:14 | ||
| So Good | Peter Rowan Bluegrass Band, Gillian Welch, Dave Rawlings | 2:46 | ||
| Wedding Bells | Buddy Miller, Richard Thompson | 4:45 | ||
| Love Is so Easy | Hayes Carll | 3:04 | ||
| Love Is Just A Wrecking Ball | Del Barber | 4:20 | ||
| Highway 17 | Rodney Crowell | 4:54 | ||
| Feed My Monkey | Ramsay Midwood | 3:18 | ||
| The River's Gonna Run | Buddy & Julie Miller | 3:59 | ||
| The Winner | Kris Kristofferson | 4:58 | ||
