| Hard Is the Fall | Jay Farrar | 2:29 | ||
| Angeline | James McMurtry | 4:04 | ||
| The Ballad of Bitter Honey | Eef Barzelay | 3:34 | ||
| All in Down and Out | Jake Xerxes Fussell | 3:13 | ||
| Don't Be Afraid of Your Anger | Clem Snide | 3:20 | ||
| Sponge | Vic Chesnutt | 3:32 | ||
| Magnolia Tree | Truckstop Honeymoon | 3:47 | ||
| Ollie McGee | Richard Buckner | 1:46 | ||
| The Hardest Thing | Cary Ann Hearst | 3:50 | ||
| The Trip | Dave Rawlings Machine | 10:55 | ||
| Simple Twist of Fate | Jeff Tweedy | 3:43 | ||
| Everybody Wants to Feel Like You | John Prine | 3:09 | ||
| It Just Dawned on Me | John Doe, The Sadies | 2:33 | ||
| Thanks for Nothing | Middle Brother, John McCauley, Matthew Vasquez, Taylor Goldsmith | 3:44 | ||
| Diamond Bell | The Felice Brothers | 6:16 | ||
| Kids In The Street | Justin Townes Earle | 3:53 | ||
| My Morphine | Hurray For The Riff Raff | 4:05 | ||
| Bug | Vic Chesnutt | 3:17 | ||
| The Bottom of the World | Bottom of the World | 4:30 | ||
| Absentminded Melody | Joel Plaskett | 1:39 | ||
| Better Part of an Hour | The Guthries | 4:35 | ||
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| Lonesome Whistle | Billy Bragg, Joe Henry | 2:53 | ||
| Portrait | Richard Buckner | 3:10 | ||
| Handful of Stars | Peter Bruntnell | 4:29 | ||
| Oh Sister | Andrew Bird | 4:49 | ||
| Clumps | Lydia Loveless | 2:00 | ||
| Strange Faces | Daniel Romano | 3:00 | ||
| Ionlanthe | James McMurtry | 4:30 | ||
| That's How Every Empire Falls | John Prine | 5:34 | ||
| Desire | Richard Buckner | 3:51 | ||
| Just a Heart | Hurray For The Riff Raff | 3:34 | ||
| Just Like Today | Charlie Parr | 5:58 | ||
| Two Different Things | Caitlin Cary, Thad Cockrell | 4:16 | ||
| Grandaddy's Mouth | Dexateens | 3:30 | ||
| Disguised As Someone Else | Joe Pug | 3:34 | ||
| Anna Leigh | The Sadies | 3:21 | ||
| Massachusetts | Scud Mountain Boys | 3:14 | ||
| Because I Love You | Doug Paisley | 2:15 | ||
| Hanging on to You | Jay Farrar | 2:51 | ||
| Blue Umbrella | John Prine | 3:53 | ||
| When You Need a Train It Never Comes | Amanda Shires | 4:14 | ||
| I Do My Father's Drugs | Joe Pug | 2:48 | ||
| Ohio River Boat Song | Will Oldham | 3:44 | ||
| Don't Wake the Scarecrow | The Felice Brothers | 4:56 | ||
| If I've Only One Time Askin' | Daniel Romano | 2:54 | ||
| Too Drunk To Dream | Whiskeytown | 2:53 | ||
| Who Carried You | Malcolm Holcombe | 3:31 | ||
| You Can't Fail Me Now | Loudon Wainwright III | 3:45 | ||
| Trampoline | Joe Henry | 4:33 | ||
