| # | Artist | Songs |
|---|---|---|
| 1 | Willie Nelson | 238 |
| 2 | The Mavericks | 122 |
| 3 | Intocable | 100 |
| 4 | Zach Bryan | 93 |
| 5 | Emmylou Harris | 66 |
| 6 | Elle King | 43 |
| 7 | Lucero | 41 |
| 8 | Wilco | 38 |
| 9 | Randy Newman | 38 |
| 10 | The Band | 27 |
| 11 | Koe Wetzel | 25 |
| 12 | Steve Earle | 24 |
| 13 | Lucinda Williams | 22 |
| 14 | Old 97's | 19 |
| 15 | The Avett Brothers | 15 |
| 16 | Cross Canadian Ragweed | 14 |
| 17 | The Civil Wars | 14 |
| 18 | City And Colour | 14 |
| 19 | Robbie Fulks | 12 |
| 20 | Shaboozey | 12 |