| # | Title | Artist | Length |
|---|
| 1 | The Gambler | Kenny Rogers | 3:30 |
| 2 | Whiskey River | Willie Nelson | 4:04 |
| 3 | I Walk the Line | The Everly Brothers | 2:37 |
| 4 | Hard Rock Bottom of Your Heart | Randy Travis | 4:02 |
| 5 | Return of the Grievous Angel | Gram Parsons | 4:23 |
| 6 | Honey Bee | Blake Shelton | 3:30 |
| 7 | Willin' | Little Feat | 2:54 |
| 8 | Cowgirl in the Sand | The Byrds | 3:24 |
| 9 | Kentucky Rain | Eddie Rabbitt | 3:57 |
| 10 | Constant Craving | k.d. lang | 4:29 |
| 11 | Sticks and Stones | Tracy Lawrence | 3:37 |
| 12 | Sidewalks of the City | Lucinda Williams | 3:45 |
| 13 | Drunkard's Dream | Gene Parsons | 2:38 |
| 14 | The Silver Tongued Devil and I | Kris Kristofferson | 3:36 |
| 15 | Tennessee | Glen Campbell | 3:04 |
| 16 | Daddy's Hands | Holly Dunn | 3:29 |
| 17 | Love Be Still | Trick Pony | 4:15 |
| 18 | I'm So Lonesome I Could Cry | The Everly Brothers | 2:54 |
| 19 | My Tennessee Mountain Home | Maria Muldaur | 3:28 |
| 20 | Chastity's Song (Band of Thieves) | Cher | 3:01 |