| Last Train | Arlo Guthrie | 3:06 | |
| Hasten Down the Wind | Warren Zevon | 2:32 | |
| Old Five and Dimers Like Me | Billy Joe Shaver | 2:41 | |
| Big Cheeseburgers and Good French Fries | Blaze Foley | 3:23 | |
| Longer Than You've Been Alive | Old 97's | 5:52 | |
| Shores of Galilee | Shinyribs | 4:43 | |
| Old Shoes | Tom Waits | 4:25 | |
| Codeine | Jason Isbell and the 400 Unit | 5:44 | |
| Oval Room | Blaze Foley | 4:04 | |
| Mental Cruelty (feat. Kacey Musgraves) | John Prine, Kacey Musgraves | 2:23 | |
| Resignation | Paul Cauthen | 3:41 | |
| Down in My Hometown | The Flatlanders | 2:45 | |
| Mexican Cowboy | Willie Watson | 3:53 | |
| Tennessee Song | Margo Price | 4:40 | |
| Six Pack of Beer and a Pack of Cigarettes | Erik Koskinen | 3:59 | |
| Little Guys | Slaid Cleaves | 3:02 | |
| 4&20 Blues | Jeffrey Foucault | 2:58 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Far From Home | Western Centuries | 3:52 | |
| Truck Driving Man | New Riders of the Purple Sage | 6:24 | |
| Unlock more with Songs Like X Pro |
| Fat Boy | Blaze Foley | 2:37 | |
| Souvenirs | John Prine | 3:42 | |
| I Got Found | Sam Doores, Riley Downing, The Tumbleweeds | 3:37 | |
| Anytime | Arlo Guthrie | 1:50 | |
| Right Where I Belong | The Flatlanders | 4:06 | |
| Roving Gambler | Hart Valley Drifters, Jerry Garcia | 3:45 | |
| Take Home Pay | Slaid Cleaves | 2:51 | |
| Rain Roll In | Eilen Jewell | 2:47 | |
| The Juarez Device (aka Texican Badman) | Terry Allen | 1:22 | |
| Yes I Guess They Oughta Name a Drink After You | John Prine | 2:10 | |
| Six Volts | Fred Eaglesmith | 2:23 | |
| Steel Rail Blues | Gordon Lightfoot | 2:49 | |
| Sweet Tequila Blues | Chip Taylor, Carrie Rodriguez | 3:15 | |
| 12 Bar Blues | Aaron Lee Tasjan | 5:04 | |
| I Like Trains | Fred Eaglesmith | 3:30 | |
| Pineola | Lucinda Williams | 4:10 | |
| Sixteen Angels Dancing 'Cross the Moon | Chip Taylor, John Prine | 3:18 | |
| Lake Marie | John Prine | 6:00 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| Accidentally Like a Martyr | Warren Zevon | 3:06 | |
| Monster Truck | Ramsay Midwood | 3:30 | |
| Lily, Rosemary and the Jack of Hearts | Tom Russell | 9:44 | |
| The Beauty Way | Ray Wylie Hubbard | 3:29 | |
| Two More Bottles Of Wine | Delbert McClinton | 3:01 | |
| Church St. Blues | Norman Blake | 2:55 | |
| Gallo del Cielo | Tom Russell | 6:32 | |
| Jealous Man | Hoyt Axton | 1:20 | |
| You Ain't Going Nowhere | Nitty Gritty Dirt Band | 3:52 | |
