| # | Artist | Songs |
|---|---|---|
| 1 | Willie Nelson | 251 |
| 2 | Johnny Cash | 216 |
| 3 | Hank Williams, Jr. | 160 |
| 4 | Waylon Jennings | 137 |
| 5 | Marty Robbins | 99 |
| 6 | Creed Fisher | 54 |
| 7 | Cody Jinks | 54 |
| 8 | Jerry Reed | 29 |
| 9 | Koe Wetzel | 26 |
| 10 | Leon Russell | 24 |
| 11 | Michael Martin Murphey | 24 |
| 12 | The Highwaymen | 22 |
| 13 | Colter Wall | 12 |
| 14 | Nikki Lane | 8 |
| 15 | Paul Cauthen | 8 |
| 16 | Billy Strings | 8 |
| 17 | Tompall Glaser | 7 |
| 18 | Tim Montana | 4 |
| 19 | Roger Alan Wade | 3 |
| 20 | Hellbound Glory | 3 |