| Sitting On Top Of the World | Doc Watson | 3:45 | |
| Texas Tears | Terry Allen, The Panhandle Mystery Band | 4:11 | |
| Hundred Dollar Valentine | Chris Smither | 3:05 | |
| The Man Who Comes Around | Motel Mirrors, Amy LaVere, John Paul Keith, Will Sexton | 3:23 | |
| Lost On The Desert | Marty Stuart And His Fabulous Superlatives | 2:34 | |
| Desert Skies | The Marshall Tucker Band | 6:23 | |
| Bag of Weed | Grayson Capps | 5:44 | |
| Truck Stop at the End of the World | Bill Kirchen | 3:14 | |
| Slingin' Rhythm | Wayne Hancock | 3:07 | |
| The Buck Starts Here | Robbie Fulks | 3:44 | |
| Loving Her Was Easier (Than Anything I'll Ever Do Again) - Live at The Hollywood Bowl, Los Angeles, CA - April 30, 2023 | Rosanne Cash, Kris Kristofferson | 3:38 | |
| The Wonder | Kris Kristofferson | 3:09 | |
| Country Cool | Shinyribs | 3:37 | |
| I'm at Home Gettin' Hammered (While She's out Gettin' Nailed) | Jesse Dayton | 2:13 | |
| Pill Bug Blues | The Gourds | 3:59 | |
| I'm Looking for Blue Eyes | Jessi Colter | 2:16 | |
| Breakdown (A Long Way from Home) | Kris Kristofferson | 2:42 | |
| Ten More Miles to Louisiana | Tony Joe White | 2:24 | |
| Mama Needs a Margarita | Zoe Muth | 4:06 | |
| Abandonitis | Terry Allen, The Panhandle Mystery Band | 3:59 | |
| How Much I've Lied - 2002 Remaster | Gram Parsons | 2:29 | |
| Unlock more with Songs Like X Pro |
| Tear Stained Eye - 2015 Remaster | Son Volt | 4:20 | |
| Dwight Yoakam | Sarah Shook & the Disarmers | 3:40 | |
| Fried Chicken & Evil Women | Vincent Neil Emerson | 3:28 | |
| Honey I'm Homeless | The Cactus Blossoms | 3:26 | |
| Piss & Moan Blues | The Gourds | 3:17 | |
| New Delhi Freight Train | Terry Allen | 7:28 | |
| Memphis Women and Chicken | Donnie Fritts | 3:51 | |
| Sing Me on My Way | John Flynn, Arlo Guthrie, Kris Kristofferson, Kathy Mattea, Billy Swan | 5:24 | |
| High Class City Girl from the Country | Zephaniah OHora | 3:42 | |
| The Pilgrim: Chapter 33 - Live | Kris Kristofferson | 3:16 | |
| After the Storm | The Flatlanders | 3:52 | |
| My Bucket's Got a Hole in It | Chip Taylor, Carrie Rodriguez | 2:32 | |
| Streets of Baltimore - 2007 Remaster | Gram Parsons | 2:55 | |
| Yesterday's Wine (Bonus Track) [feat. George Jones & Jamey Johnson] | Blackberry Smoke, George Jones, Jamey Johnson | 4:11 | |
| Best of All Possible Worlds | Kris Kristofferson | 2:58 | |
| Greater Cincinatti | Kinky Friedman | 3:29 | |
| Night Train to Memphis | Charley Crockett | 2:19 | |
| Leavin' On My Mind | Hacienda Brothers | 2:43 | |
| Long Black Veil | Lefty Frizzell | 3:02 | |
| Pack Up Your Sorrows | Bruce Robison, Kelly Willis | 2:29 | |
| Monster Truck | Ramsay Midwood | 3:30 | |
| Jealous Man | Hoyt Axton | 1:20 | |
| Columbus Stockade Blues | Doc Watson, Richard Watson | 3:31 | |
| I Feel The Blues Moving In | Slaid Cleaves | 4:08 | |
| Black Sky | The Ozark Mountain Daredevils | 3:08 | |
| Love Makes A Fool Of Us All | Jamey Johnson, Kris Kristofferson | 3:13 | |
| Deal - Single Version | Tom T. Hall | 2:33 | |
| An Old Greyhound | Hoyt Axton | 2:54 | |
