| # | Title | Tracks | Listen |
|---|---|---|---|
| 1 | Always On My Mind | 41 |
|
| 2 | To All The Girl's I've Loved Before Julio Iglesias, Willie Nelson | 39 |
|
| 3 | On The Road Again | 38 |
|
| 4 | Mamas Don't Let Your Babies Grow Up To Be Cowboys Waylon Jennings, Willie Nelson | 35 |
|
| 5 | Beer For My Horses Toby Keith, Willie Nelson | 33 |
|
| 6 | Blue Eyes Crying In The Rain | 24 |
|
| 7 | Mendocino County Line Lee Ann Womack, Willie Nelson | 20 |
|
| 8 | Whiskey River | 17 |
|
| 9 | All Of Me | 16 |
|
| 10 | Angel Flying Too Close To The Ground | 15 |
|
| 11 | My Heroes Have Always Been Cowboys | 15 |
|
| 12 | To All The Girls I've Loved Before Willie Nelson (also Julio Iglesias) | 15 |
|
| 13 | Blue Skies | 14 |
|
| 14 | City Of New Orleans | 14 |
|
| 15 | If You've Got The Money I've Got The Time | 13 |
|
| 16 | Pancho And Lefty Merle Haggard, Willie Nelson | 13 |
|
| 17 | Georgia On My Mind | 12 |
|
| 18 | Mammas Don't Let Your Babies... Willie Nelson (also Waylon Jennings) | 12 |
|
| 19 | Good Hearted Woman Waylon Jennings, Willie Nelson | 11 |
|
| 20 | Crazy | 10 |
|