| # | Artist | Songs |
|---|---|---|
| 1 | Emmylou Harris | 67 |
| 2 | Alison Krauss | 66 |
| 3 | John Prine | 60 |
| 4 | Rodney Crowell | 44 |
| 5 | Lucero | 41 |
| 6 | Brandi Carlile | 38 |
| 7 | Wilco | 33 |
| 8 | Charley Crockett | 32 |
| 9 | Neko Case | 31 |
| 10 | Rosanne Cash | 28 |
| 11 | The Band | 26 |
| 12 | Ryan Adams | 25 |
| 13 | Steve Earle | 24 |
| 14 | Sturgill Simpson | 23 |
| 15 | Lucinda Williams | 22 |
| 16 | Nanci Griffith | 20 |
| 17 | Old 97's | 19 |
| 18 | Jack Greene | 18 |
| 19 | The Avett Brothers | 14 |
| 20 | Lyle Lovett | 14 |