| # | Artist | Songs |
|---|---|---|
| 1 | Willie Nelson | 241 |
| 2 | Bob Dylan | 124 |
| 3 | Bonnie Raitt | 70 |
| 4 | Emmylou Harris | 69 |
| 5 | Alison Krauss | 67 |
| 6 | John Prine | 63 |
| 7 | Tyler Childers | 56 |
| 8 | k.d. lang | 52 |
| 9 | Lee Ann Womack | 49 |
| 10 | Rodney Crowell | 44 |
| 11 | Brandi Carlile | 42 |
| 12 | Elle King | 42 |
| 13 | Lucero | 41 |
| 14 | Wilco | 38 |
| 15 | Neko Case | 33 |
| 16 | Charley Crockett | 32 |
| 17 | Parker McCollum | 30 |
| 18 | The Band | 29 |
| 19 | Rosanne Cash | 28 |
| 20 | James Bay | 28 |