| Old Man at the Mill | Iain Matthews | 2:30 | |
| Willin' | Commander Cody and His Lost Planet Airmen | 3:38 | |
| Low Rida | Lil Pimpin DPG, Big Pimpin', Cowboy | 1:02 | |
| Dim Lights, Thick Smoke (And Loud, Loud Music) | Manassas | 2:16 | |
| Leaving Louisiana in the Broad Daylight | Rodney Crowell | 3:24 | |
| Do You Know How It Feels to Be Lonesome? | The International Submarine Band | 3:33 | |
| Dancing the Night Away - Remastered | Amazing Rhythm Aces | 5:40 | |
| Take a Giant Step - 1969 Version | Taj Mahal | 4:15 | |
| How Can a Poor Man Stand Such Times and Live? | Ry Cooder | 2:46 | |
| Shooting Star | Danny O'Keefe | 2:39 | |
| Long May You Run - 2017 Remaster | The Stills-Young Band | 3:48 | |
| Early Morning Riser | Pure Prairie League | 5:06 | |
| Homeland Refugee | The Flatlanders | 3:58 | |
| Bend in the Water | Gordon Lightfoot | 3:00 | |
| Funny | Alvin Lee | 2:50 | |
| Luxury Liner | The International Submarine Band | 2:48 | |
| King of the Cowboys - Remastered | Amazing Rhythm Aces | 4:00 | |
| Lincoln Town | John Hiatt | 4:03 | |
| I Must Be Somebody Else You've Known | The International Submarine Band | 2:20 | |
| Stop and Start It All Again | Johnathan Edwards | 3:00 | |
| Border Lord | Kris Kristofferson | 3:37 | |
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| Damn My Nigga | Mr Creepy Loc, Cowboy, Aktive | 4:13 | |
| Grow Too Old | Bobby Charles | 4:02 | |
| Hasten Down the Wind | Warren Zevon | 2:32 | |
| The Road | Danny O'Keefe | 3:49 | |
| Steel Rail Blues | Gordon Lightfoot | 2:49 | |
| Good Time Charlie's Got the Blues | Danny O'Keefe | 2:43 | |
| Kite Woman | JD Souther | 3:06 | |
| Biloxi | Jesse Winchester | 3:19 | |
| Detroit or Buffalo | Barbara Keith | 4:31 | |
| Rise Up (Easy Rider) | Brewer & Shipley | 3:15 | |
| When the Circus Comes | Los Lobos | 3:16 | |
| Sure to Fall | Valerie June | 2:51 | |
| Burning the Ballroom Down | Amazing Rhythm Aces | 5:18 | |
| Lowlands | The Ozark Mountain Daredevils | 3:44 | |
| Ft KS | Cowboy | 3:45 | |
| At The Crossroads | Sir Douglas Quintet | 4:32 | |
| It Was Always So Easy (To Find An Unhappy Woman) | Peter Wolf | 2:40 | |
| Nobody Else's Man | Cowboy | 4:29 | |
| Ain't That Pretty | Ted Hawkins | 2:58 | |
| Anna Mani Manai | Timmy, Cowboy | 2:24 | |
| Northeast Texas Women | Willis Alan Ramsey | 5:51 | |
| It Probably Always Will | The Ozark Mountain Daredevils | 3:13 | |
| Innocence Song | Cowboy | 1:56 | |
| Steel Rail Blues | Gordon Lightfoot | 2:53 | |
| At The Crossroads - Alternate Mix | Sir Douglas Quintet | 4:37 | |
| B.B. King Medley: Sweet Little Angel/It's My Own Fault/How Blue Can You Get | Hour Glass | 7:11 | |
| There Stands The Glass | Ted Hawkins | 2:33 | |
| Cosmic Cowboy, Pt. 1 | Michael Martin Murphey | 3:57 | |