| Call Him Daylight | Hiss Golden Messenger | 3:32 | |
| The Asp and the Albatross | Freakwater | 3:10 | |
| Big Sur | Jay Farrar, Benjamin Gibbard | 3:24 | |
| Cigarettes Coffee and Booze | The Minus 5 | 4:24 | |
| Devil's in the Jukebox (with The Pariah Dogs) | Ray LaMontagne, The Pariah Dogs | 3:59 | |
| When You Need a Train It Never Comes | Amanda Shires | 4:14 | |
| Atlanta | Centro-matic | 3:52 | |
| Slow Surprise | Chris Smither | 3:42 | |
| When Bitter Met Sweet | The Honeycutters | 3:41 | |
| Biloxi | Hiss Golden Messenger | 2:51 | |
| Green Mountains and Me | Slaid Cleaves | 3:44 | |
| The El | Rhett Miller | 3:09 | |
| Brady | Backyard Tire Fire | 4:06 | |
| Hymn #35 | Joe Pug | 3:11 | |
| Black T-Shirt | Slaid Cleaves | 3:14 | |
| When You're Gone | Amanda Shires | 3:06 | |
| Friends Like Those | Robert Ellis | 4:07 | |
| North | Blackie & The Rodeo Kings | 3:20 | |
| She Don't Have to See You | Golden Smog | 4:01 | |
| Oyster and Pearl | Amy Ray, Phil Cook, Brad Cook, Justin Vernon | 4:00 | |
| Acuff-Rose | Uncle Tupelo | 2:35 | |
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| The Door Was Always Open | Joe Pug | 2:49 | |
| Feeling of Beauty | Tift Merritt | 4:01 | |
| Think About You | Eliza Gilkyson | 3:23 | |
| Where'd You Hide The Body | James McMurtry | 3:40 | |
| Red & White & Blue & Gold | Aoife O'Donovan | 3:20 | |
| Young When I Left Home | The Good Luck Thrift Store Outfit | 4:28 | |
| The Arrow | The Black Lillies, Jill Andrews | 5:11 | |
| A Good Country Mile | Kevn Kinney | 8:32 | |
| Irene (Ravin' Bomb) | Ian Noe | 3:58 | |
| Needed | Robbie Fulks | 5:07 | |
| Break of Day | Steppin' In It | 4:34 | |
| Lonesome Whistle | Watchhouse | 3:40 | |
| Walking Each Other Home | Mary Gauthier | 4:17 | |
| God Willin' & the Creek Don't Rise (with The Pariah Dogs) | Ray LaMontagne, The Pariah Dogs | 3:09 | |
| My Beloved | Diana Jones | 3:29 | |
| Cleveland County Blues | John Moreland | 3:52 | |
| Whiskey in My Whiskey | The Felice Brothers | 3:48 | |
| Ruby and Carlos | James McMurtry | 6:35 | |
| The Calm and the Crying Wind | Trampled by Turtles | 3:58 | |
| Baltimore | Israel Nash | 5:20 | |
| Mostly Water | Bap Kennedy | 3:23 | |
| 18 Wheels | Fred Eaglesmith | 5:01 | |
| Just By Myself | Greg Brown | 6:50 | |
| Daydreaming | Middle Brother, John McCauley, Matthew Vasquez, Taylor Goldsmith | 4:50 | |
| The Way | Scott Miller | 3:46 | |
| Please Do Not Let Me Go | Ryan Adams | 3:35 | |
| Danny’s Song | Tift Merritt | 2:08 | |
| Another Free Woman | Blackie & The Rodeo Kings, Sara Watkins | 3:30 | |
