| River | David Allan Coe | 2:13 | |
| Down in My Hometown | The Flatlanders | 2:45 | |
| When I Loved Her | Kris Kristofferson | 3:02 | |
| The L&N Don't Stop Here Anymore | June Carter Cash | 2:48 | |
| Hurt So Bad | Jaime Wyatt, Shooter Jennings | 3:49 | |
| I Never Picked Cotton | Roy Clark | 2:39 | |
| House of the White Rose Boquet | Ray Wylie Hubbard | 3:23 | |
| I Heard That You've Been Laying My Old Lady | Rusty Wier | 5:02 | |
| Needle & Thread | Eilen Jewell | 3:40 | |
| These Cowboys Born out of Their Time | Gretchen Peters | 4:12 | |
| Don't Speak in English | Chip Taylor, Carrie Rodriguez | 4:01 | |
| If I Needed You | Doc & Merle Watson | 2:36 | |
| Forgotten Coast | James McMurtry | 3:34 | |
| Steel Rail Blues | Gordon Lightfoot | 2:49 | |
| Cocaine Carolina | David Allan Coe | 2:46 | |
| Far Away | Tom Rush | 3:13 | |
| The Last Thing I Needed, the First Thing This Morning | Gary P. Nunn | 4:40 | |
| Carryin' on This Way | Dale Watson | 3:46 | |
| Trudy | The Charlie Daniels Band | 4:48 | |
| The Watchman's Gone | Gordon Lightfoot | 4:18 | |
| Star-Studded Nights | Ed Bruce | 2:40 | |
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| Childish Things | James McMurtry | 4:35 | |
| Jesus Was a Capricorn (Owed to John Prine) | Kris Kristofferson | 2:29 | |
| Someone To Give My Love To | Johnny Paycheck | 3:06 | |
| Just Someone I Used To Know | Buddy Miller, Nikki Lane | 2:22 | |
| (Ghost) Riders in the Sky: A Cowboy Legend | Charlie Daniels | 3:38 | |
| My Bucket's Got a Hole in It | Chip Taylor, Carrie Rodriguez | 2:32 | |
| The Angels Rejoiced Last Night - 2006 Remaster | Gram Parsons | 2:24 | |
| Living Legend | The Highwaymen, Willie Nelson, Johnny Cash, Waylon Jennings, Kris Kristofferson | 3:58 | |
| High Class City Girl from the Country | Zephaniah OHora | 3:42 | |
| Golden Ring - Single Version | Tammy Wynette | 3:01 | |
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| The Highway Callin' | Fred Eaglesmith | 4:34 | |
| Last Train | Arlo Guthrie | 3:06 | |
| Rough Edges | Fred Eaglesmith | 4:04 | |
| That's All It Took - 2002 Remaster | Gram Parsons | 3:01 | |
| Must Be the Whiskey | Chip Taylor, Carrie Rodriguez | 3:59 | |
| Hobo's Lullaby | Rita Coolidge, Kris Kristofferson | 5:01 | |
| Lion In Winter | Hoyt Axton | 3:23 | |
| Forever Has Come To An End | Buddy & Julie Miller | 2:50 | |
| Dust Down A Country Road | John Hiatt | 4:04 | |
| The Road Goes On Forever | Joe Ely | 4:33 | |
| Drinkin' Days | Slaid Cleaves | 4:25 | |
| Countryfied | Mel McDaniel | 2:38 | |
| Lonesome Blues | Shooter Jennings | 3:59 | |
| Cosmic Cowboy, Pt. 1 | Michael Martin Murphey | 3:57 | |
| I'm So Lonesome I Could Cry | Hank Williams | 2:48 | |
| The Winner | Kris Kristofferson | 4:58 | |
| Ready For The Times To Get Better | Crystal Gayle | 2:25 | |
