| # | Artist | Songs |
|---|---|---|
| 1 | Emmylou Harris | 67 |
| 2 | John Prine | 60 |
| 3 | Tyler Childers | 50 |
| 4 | Rodney Crowell | 44 |
| 5 | Lucero | 41 |
| 6 | Orville Peck | 38 |
| 7 | Wilco | 33 |
| 8 | Charley Crockett | 32 |
| 9 | Neko Case | 31 |
| 10 | Shelby Lynne | 29 |
| 11 | Rosanne Cash | 28 |
| 12 | Kasey Chambers | 27 |
| 13 | Hank Williams III | 27 |
| 14 | Ryan Adams | 25 |
| 15 | Steve Earle | 24 |
| 16 | Sturgill Simpson | 23 |
| 17 | Lucinda Williams | 22 |
| 18 | Corb Lund | 20 |
| 19 | Old 97's | 19 |
| 20 | Blue Rodeo | 18 |