| Old North Side | Malcolm Holcombe, Iris DeMent | 4:06 | |
| Watching the Wheels | Chatham County Line | 3:53 | |
| Think About You | Eliza Gilkyson | 3:23 | |
| When You Need a Train It Never Comes | Amanda Shires | 4:14 | |
| More and More, Less and Less | Delbert McClinton & Glen Clark | 2:53 | |
| 65 Falcon | Rod Picott | 3:27 | |
| I Am the Big Easy | Ray Bonneville | 4:37 | |
| Turpentine | Kris Kristofferson | 3:06 | |
| Primer Gray | Slaid Cleaves | 3:58 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| The Man Who Couldn't Cry | Loudon Wainwright III | 6:15 | |
| Every Time You Leave | Shelby Lynne, Allison Moorer | 2:23 | |
| Another Despair | Malcolm Holcombe | 2:42 | |
| Train to Birmingham | Kevin Welch | 4:13 | |
| Taxes on the Farmer Feeds Us All | Ry Cooder | 3:56 | |
| Let's Invite Them Over (feat. Iris DeMent) | John Prine, Iris DeMent | 2:11 | |
| Take This Hammer (feat. The Fairfield Four) | Willie Watson, The Fairfield Four | 2:59 | |
| Clean Getaway | Kieran Kane, Kevin Welch, Fats Kaplin | 2:50 | |
| Life is Fine | Tom Rush | 3:39 | |
| Lavender Blue (with Iris Dement) | Keith Sykes, Iris DeMent | 3:05 | |
| Voice of Midnight | Slaid Cleaves | 3:55 | |
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| Baby Doll | Malcolm Holcombe | 2:31 | |
| Can't Find My Way Home - Bonus Track | Rosie Flores | 4:12 | |
| Flat Top Guitar | Ana Egge | 2:50 | |
| Dusty Old Man | Tift Merritt | 3:47 | |
| Sweet Georgia | Malcolm Holcombe | 3:17 | |
| Ten Miles Down the Nine Mile Road | Scott Miller | 4:13 | |
| Millionaire | Kevin Welch | 3:59 | |
| The Good Guys (Dick Tracy) | Amanda Anne Platt & the Honeycutters | 4:37 | |
| Stitch In Time | Pharis & Jason Romero | 3:51 | |
| Slippin' | Amanda Shires | 2:39 | |
| White Girl | The Milk Carton Kids | 3:44 | |
| No Goodwill Stores In Waikiki | Gurf Morlix | 3:09 | |
| Still Fighting the War | Slaid Cleaves | 2:56 | |
| People Get Old | Lori McKenna | 3:42 | |
| Every Pilgrim Needs a Highway | Craig Market, Thomm Jutz | 3:32 | |
| My Heart Aches | Eliza Gilkyson | 3:49 | |
| Sparrows and Sparrows | Malcolm Holcombe | 2:48 | |
| One Red Rose | Iris DeMent | 3:07 | |
| Shoulda Been Done | Kieran Kane, Rayna Gellert | 2:10 | |
| River Song | Tom Rush | 3:56 | |
| The Way It Dimmed | Amanda Shires | 2:11 | |
| Shy Star | Ray Bonneville | 4:04 | |
| Something To Me | Tift Merritt | 4:09 | |
| Pallbearer | Josh Turner, Iris DeMent, Marty Stuart | 4:32 | |
| Dancing With The Women At The Bar | Whiskeytown | 4:38 | |
| Satin Sheets | Willis Alan Ramsey | 2:39 | |
| Tobacco Road | Colvin & Earle | 2:49 | |
| Bidin’ My Time | Chris Hillman | 2:59 | |