| # | Artist | Songs |
|---|---|---|
| 1 | Willie Nelson | 236 |
| 2 | Waylon Jennings | 128 |
| 3 | Cody Johnson | 95 |
| 4 | Kacey Musgraves | 73 |
| 5 | Maren Morris | 60 |
| 6 | Midland | 53 |
| 7 | Delbert McClinton | 52 |
| 8 | Tyler Childers | 50 |
| 9 | Cody Jinks | 48 |
| 10 | Rodney Crowell | 44 |
| 11 | Lucero | 41 |
| 12 | Parker McCollum | 27 |
| 13 | Slade | 25 |
| 14 | Steve Earle | 24 |
| 15 | Asleep At The Wheel | 24 |
| 16 | Gary Stewart | 24 |
| 17 | Koe Wetzel | 23 |
| 18 | The Reverend Horton Heat | 21 |
| 19 | Corb Lund | 20 |
| 20 | Aaron Watson | 19 |