| Little Sadie | Crooked Still | 2:35 | |
| The Legend of Jeremiah Johnson | Les Stroud | 2:57 | |
| Where Legends Are Born | Hobo Jim | 2:41 | |
| Hallelujah, I'm a Bum | Harry McClintock | 2:57 | |
| A Million Ways To Die | Alan Jackson | 2:28 | |
| When A Cowboy Trades His Spurs For Wings | Willie Watson & Tim Blake Nelson | 2:34 | |
| Fraulein (feat. Tyler Childers) | Colter Wall, Tyler Childers | 2:23 | |
| That's The Way It Is | Daniel Lanois | 4:08 | |
| Ain't I Right | Jane Archer and the Reactionaries | 3:00 | |
| Gettin' Down on the Mountain | Corb Lund | 3:28 | |
| The Railroad | Goodnight, Texas | 4:10 | |
| Boil Them Cabbage Down | The Johnson Boys | 1:42 | |
| I Wish I Was in Dixie | The Houghton Weavers | 2:37 | |
| They Call the Wind Maria | Robert Horton | 3:27 | |
| Penitentiary Blues (Original Starday Recording) | Charlie Monroe | 1:51 | |
| Take it from Day to Day | Stan Rogers | 3:26 | |
| Which Side are You On? | The Almanac Singers | 2:11 | |
| (Pardon Me) I've Got Someone to Kill | Johnny Paycheck | 2:56 | |
| Deadman's Gun (From Red Dead Redemption) | Ashtar Command | 4:15 | |
| When I Get to Heaven | John Prine | 3:42 | |
| John Paul Jones | Tommy Horton | 1:47 | |
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| Big Cheeseburgers and Good French Fries | Blaze Foley | 2:29 | |
| I'm the Only Hell (Mama Ever Raised) | Johnny Paycheck | 3:09 | |
| Snakes and Waterfalls | Nick Shoulders | 4:02 | |
| Carefree Drifter | David Rawlings & Gillian Welch | 0:49 | |
| Run Rufus Run | Dale Ann Bradley | 3:28 | |
| Clay Pigeons | Blaze Foley | 3:00 | |
| Kinky Boots | The Irish Brigade | 4:22 | |
| Dust In A Baggie | Billy Strings, Don Julin | 2:29 | |
| Crosscut Saw | Van Wagner | 4:28 | |
| In the Shadow of the Valley | Don Burnham | 3:46 | |
| When I Die, Just Let Me Go To Texas | Ed Bruce | 3:11 | |
| My Old Kentucky Home, Goodnight | John Prine | 3:45 | |
| A Little Log Shack I Can Always Call My Home | Wilf Carter | 3:06 | |
| Episode 2 (Orphans, Cougars & What Not) | Jomo and the Possum Posse | 2:00 | |
| Please Don't Bury Me | John Prine | 2:51 | |
| Phantom 309 | Red Sovine | 3:29 | |
| Watching The Apples Grow | Stan Rogers | 1:52 | |
| Where The Wild, Wild Flowers Grow | Ola Belle Reed | 2:29 | |
| River Boy | Waylon Jennings | 2:44 | |
| The Silver Ghost | Merle Haggard, The Strangers | 3:25 | |
| The Gambler | Kenny Rogers | 3:34 | |
| If It Hadn't Been For Love | The Steeldrivers | 3:59 | |
| The Devil's Right Hand | The Highwaymen | 3:14 | |
| Thanks A Lot | Ernest Tubb | 2:34 | |
| Night Rider's Lament | Jerry Jeff Walker | 4:49 | |
| Rye Whiskey | Tex Ritter | 3:14 | |
| The Game | Lonesome River Band | 2:55 | |
| Pick Along | Jim Mills | 1:59 | |
