| Pop Pop | Durden, Cowboy, Fauss, Gizmoh | 4:17 | |
| Run Gypsy Run | Dickey Betts, Great Southern | 3:27 | |
| Cortez Sail | Terry Allen | 6:10 | |
| Ohoopee River Bottom Land | Larry Jon Wilson | 3:41 | |
| Love in the Sweetest Amnesty | Chris Hillman | 3:43 | |
| Old Man at the Mill | Iain Matthews | 2:30 | |
| Marie's Theme - Alternate Version | Michael Nesmith | 4:10 | |
| Getaway Cars | Cowboy | 4:45 | |
| Love and Satisfy | Manassas | 1:57 | |
| Propinquity | Iain Matthews | 2:51 | |
| Border Lord | Kris Kristofferson | 3:37 | |
| Do You Know How It Feels to Be Lonesome? | The International Submarine Band | 3:33 | |
| Snakes on Everything | Little Feat | 3:06 | |
| Two Can Do It Too | Amazing Rhythm Aces | 4:27 | |
| Rise Up (Easy Rider) | Brewer & Shipley | 3:15 | |
| Atlanta's Burning Down | Dickey Betts, Great Southern | 4:30 | |
| America | Kenny Knight | 3:03 | |
| Sailin' Shoes | Little Feat | 2:51 | |
| Daytime Friend | Delia Finn | 3:16 | |
| You and Me | Grinderswitch | 2:51 | |
| How Can I Miss You When You Won't Go Away | Dan Hicks & His Hot Licks | 2:39 | |
Unlock more with Songs Like X Pro |
| Southbound | Commander Cody and His Lost Planet Airmen | 2:20 | |
| Smokey Put the Sweat On Me | Kris Kristofferson | 3:08 | |
| Texican Badman | Peter Rowan | 2:05 | |
| Too Many Choices | Cowboy | 2:46 | |
| Carefree Country Day | Buffalo Springfield | 2:41 | |
| Shooting Star | Danny O'Keefe | 2:39 | |
| Bend in the Water | Gordon Lightfoot | 3:00 | |
| The End Is Not in Sight (The Cowboy Tune) - Remastered | Amazing Rhythm Aces | 3:50 | |
| Teardrops Will Fall | Ry Cooder | 3:05 | |
| All Mama's Children | J.J. Cale | 2:23 | |
| Mama Nantucket | Michael Nesmith, The First National Band | 2:39 | |
| Low Rida | Lil Pimpin DPG, Big Pimpin', Cowboy | 1:02 | |
| Rocky Top | Dillard & Clark | 2:46 | |
| OVERDOSE | Tonymuthaphukkng, Cowboy, ENOIS SCROGGINS | 4:00 | |
| At The Crossroads | Sir Douglas Quintet | 4:32 | |
| I Had My Hopes Up High - 2022 Remaster | Joe Ely | 3:31 | |
| Takin It All The Way | Cowboy | 3:07 | |
| Tule's Blues - Remastered | Warren Zevon | 3:35 | |
| Where it Starts | Jhorn, Cowboy | 4:14 | |
| Everybody Knows Your Name | Cowboy | 4:44 | |
| It's A Good Night For Singing | Jerry Jeff Walker | 3:41 | |
| Cowboy On The Run | Quicksilver Messenger Service | 3:15 | |
| Breaux Bridge Rag | Clarence "Gatemouth" Brown | 2:58 | |
| Alone | stilz moore, Cowboy | 4:12 | |
| Don’t You Cry For Me | Ronnie Lane | 4:27 | |
| Shouldn't Have Took More Than You Gave | Dave Mason | 6:02 | |
| North Cumberland Blues | Jerry Jeff Walker | 3:28 | |
| Treat Me Like A Saturday Night - 2022 Remaster | Joe Ely | 3:03 | |