| 'Til I Get It Right | John Doe, The Sadies | 3:19 | |
| When New York Had Her Heart Broke | John Hiatt | 5:08 | |
| After the Rain | Chuck Prophet | 3:35 | |
| Streets of Baltimore - 2007 Remaster | Gram Parsons | 2:55 | |
| Walkin' to New Orleans | Gurf Morlix | 4:38 | |
| Old Enough (feat. Ricky Scaggs and Ashley Monroe) | The Raconteurs, Ricky Scaggs, Ashley Monroe | 5:45 | |
| Lost Highway | The Handsome Family | 2:59 | |
| Meat Off the Bone | The Gourds | 3:46 | |
| When You Need a Train It Never Comes | Amanda Shires | 4:14 | |
| Clay Pigeons | Gurf Morlix | 3:25 | |
| Pale Blue Eyes | Alejandro Escovedo | 6:15 | |
| Harvest Moon Blues | Zoe Muth and the Lost High Rollers | 4:46 | |
| Winsome Smile | Chris Smither | 3:34 | |
| A Little Bit of Bad | NRBQ | 3:21 | |
| Myrna Lee | Blue Mountain | 3:45 | |
| Ford Econoline | Chuck Prophet | 3:41 | |
| Midnight Train | David Rawlings | 3:18 | |
| Clear Night | The Gourds | 2:41 | |
| Back of a Bible | Patterson Hood | 4:28 | |
| Bloody 98 | Blue Mountain | 2:47 | |
| Breakdown On 20th Ave. South | Buddy & Julie Miller, Buddy Miller, Julie Miller | 3:54 | |
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| Mama Bake a Pie (Daddy Kill a Chicken) | Drive-By Truckers | 3:19 | |
| Ruby | Dave Rawlings Machine | 4:54 | |
| Sure to Fall | Valerie June | 2:51 | |
| The Man Who Couldn't Cry | Loudon Wainwright III | 6:15 | |
| Let's Go Running | Blue Mountain | 4:49 | |
| Donald And Lydia | Steve Goodman | 4:51 | |
| You're Still On My Mind | Carrie Rodriguez | 2:56 | |
| Leaving Time | Patterson Hood | 3:31 | |
| Wasn't Born To Follow | The Sadies | 2:29 | |
| Brand New Heartache - 2006 Remaster | Gram Parsons | 2:26 | |
| He Don't Care About Me | Kelly Willis | 2:31 | |
| If I Can't Trust You with a Quarter (How Can I Trust You with My Heart?) | Zoe Muth and the Lost High Rollers | 5:07 | |
| Unforgiven | Bap Kennedy | 3:37 | |
| Harper Valley Pta | Bruce Robison, Kelly Willis | 3:45 | |
| My Old Friend | John Hiatt | 3:50 | |
| Hush, Sorrow | Buddy & Julie Miller, Buddy Miller, Julie Miller | 4:02 | |
| How I Got To Memphis | The V-Roys | 4:38 | |
| Do It | Jesse Winchester | 1:27 | |
| Rock Salt And Nails | Buddy & Julie Miller | 4:17 | |
| Broke Down | Slaid Cleaves | 3:10 | |
| Spookin' The Horses | Fred Eaglesmith | 4:07 | |
| Let Your Loss Be Your Lesson | Robert Plant, Alison Krauss | 4:01 | |
| I Feel The Blues Moving In | Slaid Cleaves | 4:08 | |
| Lily, Rosemary and the Jack of Hearts | Tom Russell | 9:44 | |
| Long Black Veil | Rosanne Cash, Jeff Tweedy | 3:10 | |
| It Was Always So Easy (To Find An Unhappy Woman) | Peter Wolf | 2:40 | |
| Gone To Texas | Terry Allen | 6:22 | |
| Chicago | Ramsay Midwood | 4:50 | |
