| # | Artist | Songs |
|---|---|---|
| 1 | Willie Nelson | 235 |
| 2 | Waylon Jennings | 127 |
| 3 | Cody Johnson | 94 |
| 4 | Kacey Musgraves | 73 |
| 5 | Maren Morris | 62 |
| 6 | Midland | 53 |
| 7 | Delbert McClinton | 51 |
| 8 | Cody Jinks | 48 |
| 9 | Rodney Crowell | 43 |
| 10 | Parker McCollum | 27 |
| 11 | Slade | 25 |
| 12 | Gary Stewart | 24 |
| 13 | Asleep At The Wheel | 23 |
| 14 | Steve Earle | 23 |
| 15 | The Reverend Horton Heat | 21 |
| 16 | Aaron Watson | 19 |
| 17 | Eli Young Band | 17 |
| 18 | Pat Green | 17 |
| 19 | Whiskey Myers | 17 |
| 20 | Kevin Fowler | 16 |