| Mississippi You're On My Mind | Jesse Winchester | 3:26 | |
| Montgomery in the Rain | Steve Young | 4:25 | |
| Rich Man's World | Eilen Jewell | 2:55 | |
| Old Shoes | Tom Waits | 4:25 | |
| Borderline | Eliza Gilkyson | 2:42 | |
| The Juarez Device (aka Texican Badman) | Terry Allen | 1:22 | |
| Accidentally Like a Martyr | Warren Zevon | 3:06 | |
| I Drink Beer | Dan Reeder | 2:53 | |
| The Learned Man | F. J. McMahon | 2:40 | |
| You Cared Enough to Lie | Eilen Jewell | 2:47 | |
| Five Hearts Breaking | Alejandro Escovedo | 4:10 | |
| Candy | Dave Rawlings Machine | 4:10 | |
| Last Train | Arlo Guthrie | 3:06 | |
| If I Cant Win | The Cactus Blossoms | 3:17 | |
| Third Rate Romance | Jesse Winchester | 3:36 | |
| Those Were (Could've Been) the Days | The Deslondes, Sam Doores | 2:29 | |
| Wrote A Song For Everyone | Mavis Staples | 3:47 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Just Like That (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:30 | |
| All of Your Stories | Jesse Winchester | 2:33 | |
| Dusty Old Man | Tift Merritt | 3:47 | |
| Unlock more with Songs Like X Pro |
| My Tennessee Mountain Home | Maria Muldaur | 3:31 | |
| Do It | Jesse Winchester | 1:27 | |
| Do You Know How It Feels to Be Lonesome? | The International Submarine Band | 3:33 | |
| Hey Little Darlin' | Zoe Muth | 3:30 | |
| Yankee Lady | Jesse Winchester | 4:02 | |
| Nobody Wants to Be You | Dan Reeder | 2:08 | |
| I Don't Care - Remastered | Justin Townes Earle | 1:55 | |
| Shake Sugaree | Rhiannon Giddens | 4:24 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Desperado | The Cactus Blossoms | 2:46 | |
| Yum Yum | The Deslondes, Riley Downing, Dan Cutler, Sam Doores, Cameron Snyder | 2:56 | |
| Wallflower | Doug Sahm | 2:39 | |
| Cowboy Song | Dan Reeder | 2:35 | |
| Defying Gravity | Jesse Winchester | 2:41 | |
| Billy the Kid | Ry Cooder | 3:48 | |
| Folsom Prison Blues / That's All Right | The International Submarine Band | 4:23 | |
| Man That I've Become | Nick Lowe | 2:53 | |
| Cortez Sail | Terry Allen | 6:10 | |
| Feed My Monkey | Ramsay Midwood | 3:18 | |
| My Last Goodbye | Ted Hawkins | 3:27 | |
| Groovy Little Things | Ted Hawkins | 3:29 | |
| Poor Boy, Long Ways From Home | Mississippi John Hurt | 2:14 | |
| A Hard Rain's Gonna Fall | The Staple Singers | 7:31 | |
| Fishing With Bill | Bill Morrissey, Greg Brown | 4:32 | |
| It Probably Always Will | The Ozark Mountain Daredevils | 3:13 | |
| Coffee Blues | Mississippi John Hurt | 3:46 | |
| Goodbye Old Missoula | Willis Alan Ramsey | 5:03 | |
| That's How Strong My Love Is | Steve Young | 3:41 | |
