| From the Bottle to the Bottom | Kris Kristofferson | 2:57 | |
| D.O.A. (Drunk on Arrival) | Johnny Paycheck | 2:41 | |
| Life is Fine | Tom Rush | 3:39 | |
| Kaw-Liga | Charley Pride | 2:42 | |
| Still Feeling Blue - 2002 Remaster | Gram Parsons | 2:43 | |
| I'd Jump the Mississippi | Caleb Klauder, Reeb Willms | 2:51 | |
| If I Can't Trust You with a Quarter (How Can I Trust You with My Heart?) | Zoe Muth and the Lost High Rollers | 5:07 | |
| Only the Song Survives | John Hiatt | 4:00 | |
| Me and Bobby McGee | Gordon Lightfoot | 3:46 | |
| Watermelon Time In Georgia - Single Version | Lefty Frizzell | 2:14 | |
| Driving Nails in my Coffin | Ramblin' Jack Elliott | 1:54 | |
| Drinkin' Days | Slaid Cleaves | 4:52 | |
| Kiss the World Goodbye | Kris Kristofferson | 3:00 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Midnight Communion | Delbert McClinton | 4:10 | |
| Hall of Angels | Kris Kristofferson | 3:59 | |
| Thunderbird | John Hiatt | 4:04 | |
| King Cotton | The Secret Sisters | 3:12 | |
| Who's to Bless and Who's to Blame | Kris Kristofferson | 3:29 | |
| The Last Cowboy Song | Ed Bruce | 4:57 | |
| Louisiana Man | Doug Kershaw | 2:35 | |
| Unlock more with Songs Like X Pro |
| Broken Freedom Song | Kris Kristofferson | 5:23 | |
| Truck Drivin' Man | Buck Owens | 2:34 | |
| Oh Set a Light | Chip Taylor, Carrie Rodriguez | 3:44 | |
| Trouble (with Delbert McClinton) | Iris DeMent, Delbert McClinton | 7:33 | |
| I Like Trains | Fred Eaglesmith | 3:30 | |
| Jersey Girl | Hal Ketchum | 3:42 | |
| Angels Love Bad Men | The Highwaymen, Willie Nelson, Johnny Cash, Waylon Jennings, Kris Kristofferson | 3:32 | |
| Thank You for a Life | Kris Kristofferson | 3:44 | |
| Jesus Take the Wheel (and Drive Me to a Bar) | Sam Outlaw | 3:19 | |
| The Habit | Don Edwards | 3:18 | |
| Time Stands Still | Chris Smither | 3:45 | |
| You Cared Enough to Lie | Eilen Jewell | 2:47 | |
| I'm Just an Old Chunk of Coal (But I'm Gonna Be a Diamond Some Day) | John Anderson | 3:47 | |
| Sometimes I Do | Ernest Tubb | 2:06 | |
| West Texas Heaven | Kimmie Rhodes | 3:07 | |
| Single Girl, Married Girl | Levon Helm | 3:19 | |
| Two More Bottles Of Wine | Delbert McClinton | 3:01 | |
| Till I Found You | Marty Stuart | 2:26 | |
| Drinkin' Days | Slaid Cleaves | 4:25 | |
| Lion In Winter | Hoyt Axton | 3:23 | |
| Stay Young | Don Williams | 3:07 | |
| Hobo's Lullaby | Rita Coolidge, Kris Kristofferson | 5:01 | |
| The Lights Of San Francisco | Logan Ledger | 5:01 | |
| My Baby's Gone | The Louvin Brothers | 2:46 | |
| Too Many Bridges To Cross Over - Remastered | Merle Haggard & The Strangers | 2:24 | |
| Last Of The Hobo Kings | Mary Gauthier | 5:50 | |
| I Dream Of Highways | Hoyt Axton | 2:35 | |
| The Sky Above And The Mud Below | Ramblin' Jack Elliott | 6:15 | |
