| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 606 |
| 2 | Ella Fitzgerald | 195 |
| 3 | Tony Bennett | 150 |
| 4 | Diana Krall | 103 |
| 5 | Billie Holiday | 79 |
| 6 | Karen Souza | 49 |
| 7 | Jamie Cullum | 43 |
| 8 | Peggy Lee | 40 |
| 9 | Nina Simone | 39 |
| 10 | Sarah Vaughan | 38 |
| 11 | Al Jarreau | 36 |
| 12 | Dinah Washington | 32 |
| 13 | Nancy Wilson | 32 |
| 14 | Louis Armstrong | 31 |
| 15 | Stacey Kent | 30 |
| 16 | Gregory Porter | 30 |
| 17 | Melody Gardot | 26 |
| 18 | Renee Olstead | 22 |
| 19 | Julie London | 17 |
| 20 | Berk and The Virtual Band | 17 |