| Amie | Pure Prairie League | 4:19 | ||
| They Killed John Henry | Justin Townes Earle | 2:46 | ||
| Saskatchewan in 1881 | Colter Wall | 2:51 | ||
| L.A. County | Lyle Lovett | 3:19 | ||
| The Outskirts | Trampled by Turtles | 5:53 | ||
| How Lucky | Kurt Vile, John Prine | 3:23 | ||
| Dog | Charlie Parr | 3:59 | ||
| Canola Fields | James McMurtry | 4:49 | ||
| Steel Rail Blues | Gordon Lightfoot | 2:49 | ||
| Manhattan Island Serenade | Vincent Neil Emerson | 2:41 | ||
| She Is My Everything | John Prine | 4:25 | ||
| I Still Sing the Old Songs | David Allan Coe | 3:41 | ||
| Desert Skies | The Marshall Tucker Band | 6:23 | ||
| You Can Have the Crown | Sturgill Simpson | 2:50 | ||
| Spanish Pipedream | John Prine | 2:41 | ||
| Hard Travelin' | Watchhouse | 2:42 | ||
| Winsome Smile | Chris Smither | 3:34 | ||
| I'm Not Drunk I'm Just Drinking | Mack Allen Smith | 2:05 | ||
| That's the Way That the World Goes 'Round | John Prine | 3:20 | ||
| Let the Mystery Be | Iris DeMent | 2:50 | ||
| Time > Breathe Reprise > | Greensky Bluegrass | 5:38 | ||
| Unlock more with Songs Like X Pro | ||||
| Cortez Sail | Terry Allen | 6:10 | ||
| Champaign, Illinois | Old 97's | 3:25 | ||
| Those Were (Could've Been) the Days | The Deslondes, Sam Doores | 2:29 | ||
| Fire on the Mountain | The Marshall Tucker Band | 3:56 | ||
| Over the Red Cedar | Charlie Parr | 4:19 | ||
| All the Pretty Colors | Sturgill Simpson | 2:18 | ||
| Dixie Chicken | Little Feat | 3:59 | ||
| On the Line | Billy Strings | 3:49 | ||
| Paradise | John Prine | 3:15 | ||
| Atlantic City | The Band | 5:14 | ||
| Jamestown Ferry | Charley Crockett | 3:06 | ||
| Bruised Orange (Chain of Sorrow) | John Prine | 5:21 | ||
| I Am a Pilgrim | The Byrds | 3:39 | ||
| On The Road Again (feat. The Fairfield Four) | Willie Watson, The Fairfield Four | 2:27 | ||
| Feed My Monkey | Ramsay Midwood | 3:18 | ||
| Steel Rail Blues | Gordon Lightfoot | 2:53 | ||
| Two More Bottles Of Wine | Delbert McClinton | 3:01 | ||
| Unknown Legend | Shovels & Rope, Shakey Graves | 4:28 | ||
| Working Man Blues | Merle Haggard | 2:36 | ||
| Ophelia - Remastered 2000 | The Band | 3:32 | ||
| Just Outside Of Austin | Lukas Nelson and Promise of the Real | 4:44 | ||
| Mama Tried - Remastered 2001 | Merle Haggard & The Strangers | 2:12 | ||
| The Road Goes On Forever | The Highwaymen | 4:41 | ||
| Goodbye Old Missoula | Willis Alan Ramsey | 5:03 | ||
| Melissa | Allman Brothers Band | 3:55 | ||
| Purple Rain | Dwight Yoakam | 4:42 | ||
| Midnight Blues | Leftover Salmon | 3:12 | ||
| Jeremiah | Sierra Ferrell | 3:03 | ||
