| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 678 |
| 2 | Ella Fitzgerald | 207 |
| 3 | Nat King Cole | 165 |
| 4 | Tony Bennett | 164 |
| 5 | Diana Krall | 107 |
| 6 | Billie Holiday | 79 |
| 7 | Norah Jones | 79 |
| 8 | Ray Charles | 69 |
| 9 | Harry Connick Jr. | 68 |
| 10 | Etta James | 65 |
| 11 | Karen Souza | 49 |
| 12 | Peggy Lee | 47 |
| 13 | Sammy Davis Jr. | 44 |
| 14 | Jamie Cullum | 43 |
| 15 | Nina Simone | 42 |
| 16 | Sarah Vaughan | 41 |
| 17 | Nancy Wilson | 39 |
| 18 | Judy Garland | 35 |
| 19 | Louis Armstrong | 34 |
| 20 | Al Jarreau | 34 |