| You Can Have Her | J.D. Crowe & The New South | 2:30 | |
| Get a Little Gonner | Bill Kirchen | 2:44 | |
| You Cared Enough to Lie | Eilen Jewell | 2:47 | |
| Something About a Train Sound | Irene Kelley | 3:17 | |
| Dirty Old Town | Kelsey Waldon | 2:41 | |
| Montana Cowboy | Caleb Klauder, Reeb Willms | 2:35 | |
| Lonely Ain't Hardly Alive | Robbie Fulks | 3:54 | |
| Philosophers and Fools | Western Centuries | 3:12 | |
| Won't You Come and Sing for Me? - 2021 Remaster | Hazel Dickens, Alice Gerrard | 2:45 | |
| My Time Is Gonna Come | Caleb Klauder | 3:22 | |
| She Will Get Lonesome | Caleb Klauder & Reeb Willms | 2:11 | |
| I Ain't Got No Home | The Tillers | 3:31 | |
| Two for the Road | JP Harris | 2:54 | |
| Song of the Bird | The Cactus Blossoms | 2:29 | |
| Live Real Lean | Sad Daddy | 3:07 | |
| Warm Guns | Western Centuries | 4:55 | |
| Been on the Rocks | Caleb Klauder, Reeb Willms | 2:18 | |
| Yelling At Me | Victor Koch | 3:33 | |
| Daddy Was a Drunk | Jason Dea West, Cassandra Girard, John L Richardson, Kevin Hayezy | 3:14 | |
| Lost in the City Lights | Johnny Falstaff | 3:34 | |
| Kentucky Girl | Larry Sparks | 2:53 | |
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| No Friend to Louisiann | Leo Rondeau | 3:34 | |
| Maybe We'll Wind up in Love | David Ball | 2:59 | |
| Come All Ye Fair And Tender Ladies (Arr. P. Isbey): Come All Ye Fair And Tender Ladies | Little Grasscals, Traditional | 3:25 | |
| Crazy Eyed Woman | Woody Pines | 2:44 | |
| Down in Pasco | Pat Reedy | 2:37 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Damn You | Sarah Shook & the Devil | 3:47 | |
| New Shoes | Caleb Klauder | 3:10 | |
| Red Dress | Lavender Country | 4:23 | |
| Come All You Virginia Girl | Foghorn Stringband | 3:07 | |
| You're the Reason Our Kids Are Ugly (feat. Nikki Lane) | JP Harris, Nikki Lane | 2:34 | |
| Freight Train Blues | The Weary Boys | 2:45 | |
| A Drink After Midnight | The Country Side Of Harmonica Sam | 2:47 | |
| All American Singer | Zephaniah OHora | 3:57 | |
| Going Down the Road Feelin' Bad | Dom Flemons | 2:38 | |
| Dear John (I Sent Your Saddle Home) | John Prine | 2:25 | |
| My Bucket's Got a Hole in It | Chip Taylor, Carrie Rodriguez | 2:32 | |
| You're the One | Caleb Klauder, Reeb Willms | 3:16 | |
| Worried Man Blues | Don Reno, Bill Harrell, The Tennessee Cut-Ups | 2:07 | |
| Blind Fiddler | Hoyt Axton | 2:29 | |
| Wish I Had My Time Again | Uncle Earl | 2:32 | |
| Poor Ellen Smith | Jim Mills | 2:31 | |
| Duncan & Brady (He's Been On The Job Too Long) | The Johnson Mountain Boys | 3:18 | |
| El Paso | Tom Russell | 5:38 | |
| Big Black Train | The Earls Of Leicester | 2:47 | |
| Floor To Crawl | James Hand | 2:49 | |
| You Can Feel It In Your Soul | The Earls Of Leicester | 3:02 | |
| If Wishes Were Horses | Claire Lynch | 2:36 | |
