| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 659 |
| 2 | Ella Fitzgerald | 202 |
| 3 | Tony Bennett | 164 |
| 4 | Nat King Cole | 152 |
| 5 | Diana Krall | 106 |
| 6 | Billie Holiday | 79 |
| 7 | Norah Jones | 75 |
| 8 | Harry Connick Jr. | 68 |
| 9 | Ray Charles | 65 |
| 10 | Etta James | 63 |
| 11 | Karen Souza | 49 |
| 12 | Peggy Lee | 46 |
| 13 | Nina Simone | 43 |
| 14 | Sammy Davis Jr. | 43 |
| 15 | Jamie Cullum | 43 |
| 16 | Sarah Vaughan | 40 |
| 17 | Nancy Wilson | 37 |
| 18 | Al Jarreau | 34 |
| 19 | Gregory Porter | 32 |
| 20 | Dinah Washington | 32 |