| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 659 |
| 2 | Ella Fitzgerald | 201 |
| 3 | Tony Bennett | 162 |
| 4 | Nat King Cole | 154 |
| 5 | Diana Krall | 106 |
| 6 | Billie Holiday | 79 |
| 7 | Norah Jones | 74 |
| 8 | Harry Connick Jr. | 68 |
| 9 | Ray Charles | 64 |
| 10 | Etta James | 62 |
| 11 | Karen Souza | 49 |
| 12 | Peggy Lee | 45 |
| 13 | Jamie Cullum | 43 |
| 14 | Sammy Davis Jr. | 42 |
| 15 | Nina Simone | 41 |
| 16 | Sarah Vaughan | 40 |
| 17 | Al Jarreau | 35 |
| 18 | Nancy Wilson | 33 |
| 19 | Gregory Porter | 32 |
| 20 | Dinah Washington | 32 |