| Wasteland of the Free | Iris DeMent | 5:15 | ||
| Long Hot Summer Day | Turnpike Troubadours | 4:12 | ||
| Life of Sin | Sturgill Simpson | 2:26 | ||
| If I Could Only Fly | Blaze Foley | 4:04 | ||
| Waltz About Whiskey | Watchhouse | 3:46 | ||
| September Doves | Lost Dog Street Band | 4:50 | ||
| Dear John (I Sent Your Saddle Home) | John Prine | 2:25 | ||
| Everything Is Free | Gillian Welch | 4:47 | ||
| Big Cheeseburgers & Good French Fries | Blaze Foley | 2:14 | ||
| I Sang The Song | Mac Wiseman, John Prine, Peter Cooper, Thomm Jutz | 3:35 | ||
| Lone Pine Hill | Justin Townes Earle | 3:03 | ||
| Black Creek | Brent Cobb | 3:32 | ||
| Please Let Me Go Round Again | Swamp Dogg, John Prine | 4:40 | ||
| She Is My Everything | John Prine | 4:25 | ||
| Over the Red Cedar | Charlie Parr | 4:19 | ||
| I Choose You | The Steeldrivers | 3:05 | ||
| Song of the South | Alabama | 3:10 | ||
| Amie | Pure Prairie League | 4:19 | ||
| Travelin' Soldier | The Chicks | 5:43 | ||
| How Lucky | John Prine | 3:38 | ||
| Lawyers, Guns and Money | Warren Zevon | 3:30 | ||
| Unlock more with Songs Like X Pro | ||||
| Gin and Juice | The Gourds | 6:23 | ||
| Snakes and Waterfalls | Nick Shoulders | 4:02 | ||
| Feathered Indians | Tyler Childers | 3:44 | ||
| Goddamn Lonely Love - Remastered | Drive-By Truckers | 5:01 | ||
| Dearly Departed (feat. Esmé Patterson) | Shakey Graves, Esmé Patterson | 3:32 | ||
| She's All I Got | Johnny Paycheck | 2:56 | ||
| Old Ties and Companions | Watchhouse | 3:08 | ||
| Early Morning Rain | Gordon Lightfoot | 3:18 | ||
| Dang Me | Roger Miller | 1:42 | ||
| Box #10 | Jim Croce | 2:27 | ||
| Diamonds & Gasoline | Turnpike Troubadours | 3:54 | ||
| Turtles All the Way Down | Sturgill Simpson | 3:08 | ||
| Angel from Montgomery | John Prine | 3:44 | ||
| Roll Um Easy | Little Feat | 2:31 | ||
| The Muse | The Wood Brothers | 3:21 | ||
| Casey Jones - 2013 Remaster | Grateful Dead | 4:25 | ||
| Kate McCannon | Colter Wall | 4:34 | ||
| Let the Mystery Be | Iris DeMent | 2:50 | ||
| Hello Trouble | Buck Owens | 1:51 | ||
| Running on Empty | Jackson Browne | 4:51 | ||
| Longhaired Redneck | David Allan Coe | 3:20 | ||
| Southern Cross - 2005 Remaster | Crosby, Stills & Nash | 4:41 | ||
| Whiskey Bent And Hell Bound | Hank Williams, Jr. | 3:08 | ||
| Joy Of My Life | Chris Stapleton | 4:34 | ||
| Luckiest Man | The Wood Brothers | 3:53 | ||
| Down To The River To Pray - From “O Brother, Where Art Thou” Soundtrack | Alison Krauss | 2:56 | ||
| Pissin' In The Wind | Jerry Jeff Walker | 4:00 | ||
| Tight Fittin' Jeans | Conway Twitty | 2:51 | ||
