| # | Artist | Songs |
|---|---|---|
| 1 | Willie Nelson | 239 |
| 2 | Johnny Cash | 207 |
| 3 | Hank Williams, Jr. | 155 |
| 4 | Waylon Jennings | 134 |
| 5 | Marty Robbins | 96 |
| 6 | Creed Fisher | 51 |
| 7 | Cody Jinks | 51 |
| 8 | Koe Wetzel | 25 |
| 9 | Jerry Reed | 24 |
| 10 | Michael Martin Murphey | 23 |
| 11 | The Highwaymen | 23 |
| 12 | Leon Russell | 20 |
| 13 | Colter Wall | 11 |
| 14 | Nikki Lane | 8 |
| 15 | Paul Cauthen | 7 |
| 16 | Billy Strings | 7 |
| 17 | Tompall Glaser | 6 |
| 18 | Dougie Poole | 2 |
| 19 | Don Bowman | 2 |
| 20 | Jaime Wyatt | 1 |