| Tex - Mex Mile | The Gourds | 3:19 | |
| Miles to Go | Eilen Jewell | 3:16 | |
| The Pilgrim, Chapter 33 | Kris Kristofferson | 3:09 | |
| Doncha Miss That Water | Malcolm Holcombe | 2:45 | |
| Me And Bobby McGee | Roger Miller | 3:16 | |
| Saginaw, Michigan | Lefty Frizzell | 3:06 | |
| You'll Never Again Be Mine | Levon Helm | 3:09 | |
| I Take My Chances | Mary Chapin Carpenter | 3:45 | |
| Mississippi You're On My Mind | Jesse Winchester | 3:26 | |
| Forgotten Coast | James McMurtry | 3:34 | |
| Different Kind Of Gone | Mary Gauthier | 3:41 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Race Among the Ruins | Gordon Lightfoot | 3:18 | |
| Life Has Its Little Ups And Downs | Charlie Rich | 3:41 | |
| 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 | |
| Steel Rail Blues | Gordon Lightfoot | 2:49 | |
| Committed to Parkview | The Highwaymen, Willie Nelson, Johnny Cash, Waylon Jennings, Kris Kristofferson | 3:20 | |
| Drunk And Lonesome (Again) | Southern Culture on the Skids | 2:53 | |
| Nobody Wins | Kris Kristofferson | 3:06 | |
| Never Cry Again | John Fullbright | 4:14 | |
| The Way I Should | Iris DeMent | 4:26 | |
| Unlock more with Songs Like X Pro |
| Borderline | Eliza Gilkyson | 2:42 | |
| Leave The Light On | Chris Smither | 3:47 | |
| Levelland | James McMurtry | 5:23 | |
| Jesus Take the Wheel (and Drive Me to a Bar) | Sam Outlaw | 3:19 | |
| Billy 4 | Gretchen Peters | 5:36 | |
| When Rita Leaves | Delbert McClinton | 4:37 | |
| I Take It On Home | Charlie Rich | 2:50 | |
| Hello In There (with Joan Baez) - Live | Kris Kristofferson, Joan Baez | 3:29 | |
| I Gotta Get Drunk (with Willie Nelson) | George Jones | 2:10 | |
| Roll Me Up | Willie Nelson, Snoop Dogg, Kris Kristofferson, Jamey Johnson | 3:25 | |
| You're Running Wild - 2003 Remaster | Emmylou Harris with Rodney Crowell | 1:43 | |
| Love Don't Live Here Anymore | Kris Kristofferson | 2:01 | |
| Lost Inside of You | Barbra Streisand, Kris Kristofferson | 2:54 | |
| Angels Love Bad Men | The Highwaymen, Willie Nelson, Johnny Cash, Waylon Jennings, Kris Kristofferson | 3:32 | |
| Truck Drivin' Man | Buck Owens | 2:34 | |
| Half-Broke Horse | Eilen Jewell | 3:26 | |
| For the Good Times | Kris Kristofferson | 3:22 | |
| Deportees | Arlo Guthrie | 3:50 | |
| Desperados Waiting for a Train | The Highwaymen, Willie Nelson, Johnny Cash, Waylon Jennings, Kris Kristofferson | 4:36 | |
| Ready For The Times To Get Better | Crystal Gayle | 2:25 | |
| High On A Mountain Top | Marty Stuart | 4:03 | |
| When The Rodeo Is Over (Where Does The Cowboy Go?) | Tanya Tucker | 4:02 | |
| Bottle To The Bottom | Dierks Bentley, Kris Kristofferson | 4:16 | |
| For The First Time | Jessi Colter | 2:40 | |
| Between The Daylight And The Dark | Mary Gauthier | 4:15 | |
| Boy From Oklahoma | Willis Alan Ramsey | 3:54 | |
| Got Me A Woman | Levon Helm | 3:12 | |
| Where Have All The Average People Gone - Single Version | Roger Miller | 3:01 | |
