| Chalk | Buddy & Julie Miller, Buddy Miller, Julie Miller | 3:40 | |
| Only She Knows | Frankie Lee | 4:04 | |
| Crooked Kind of Free | Thomas Csorba | 4:05 | |
| Lessons in Gravity | Amanda Anne Platt & the Honeycutters | 5:20 | |
| Strange Fascination | Chatham County Line, Sharon Van Etten | 4:18 | |
| Anyhow | Kelsey Waldon | 2:58 | |
| Live Forever | Willie Nelson, Lucinda Williams | 3:00 | |
| Burn One With John Prine | Roger Harvey | 3:35 | |
| Nowhere, Baby | The Secret Sisters | 4:39 | |
| Kathy | Luther Dickinson, Allison Russell, Birds of Chicago | 4:17 | |
| Pawnshop Dollar Bills | The Dead Tongues | 8:07 | |
| Back Row (Live) | Amanda Anne Platt & the Honeycutters | 4:56 | |
| I Let You Down | Yarn | 5:16 | |
| Oh My Love | The Small Glories | 3:20 | |
| National Treasure | Willy Tea Taylor, The Turkey Buzzards | 3:21 | |
| Old North State | Emily Scott Robinson | 3:12 | |
| I Still Believe in You | Sean McConnell | 3:31 | |
| I'm Only Human | Michaela Anne | 2:55 | |
| Through the Dark | Slaid Cleaves | 3:03 | |
| Lonely Love Affair | Watchhouse | 4:05 | |
| Father | Robert Ellis | 4:57 | |
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| Shoulda Been Done | Kieran Kane, Rayna Gellert | 2:10 | |
| Will You | Viv & Riley | 3:18 | |
| Vaquero | James McMurtry | 4:41 | |
| The 13th Apostle | Sean McConnell, The Wood Brothers | 3:27 | |
| Cocaine Cowboys | Ana Egge | 3:55 | |
| Birthday Song | Amanda Anne Platt & the Honeycutters | 4:15 | |
| The Band Plays On | Bob Schneider | 2:57 | |
| Wide Awake | Julian Taylor | 4:18 | |
| Sister Golden Hair | Anna Ash | 3:30 | |
| Love Is Just A Wrecking Ball | Del Barber | 4:20 | |
| Millionaire | Kevin Welch | 3:59 | |
| Rye Grass Riders | Samantha Rise | 4:02 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Good As Gold | Sarah Shook & the Disarmers | 3:13 | |
| Downtown | The Cactus Blossoms | 3:14 | |
| The Last Tear | Lilly Hiatt | 3:31 | |
| Too Stoned to Cry - 2019 Recut | Andrew Combs | 3:24 | |
| Tell Me | Kristina Murray | 3:42 | |
| Truck Stop Shower | Smooth Hound Smith | 3:10 | |
| Comin' and Goin' | Sway Wild, Birds of Chicago | 4:27 | |
| Traveling After Dark | Aaron Lee Tasjan | 3:49 | |
| It's Never Too Late to Call | Paul Thorn | 3:01 | |
| That River | Margo Cilker | 3:09 | |
| Nightmares | Gasoline Lollipops | 4:41 | |
| Back When I Cared | Lukas Nelson and Promise of the Real | 3:38 | |
| Hand Me A Light | Lukas Nelson and Promise of the Real | 3:35 | |
| 12th of June | Lyle Lovett | 4:54 | |
| Skip A Rope | Logan Ledger | 3:47 | |
