| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 604 |
| 2 | Ella Fitzgerald | 194 |
| 3 | Tony Bennett | 147 |
| 4 | Nat King Cole | 140 |
| 5 | Diana Krall | 105 |
| 6 | Billie Holiday | 79 |
| 7 | Norah Jones | 73 |
| 8 | Harry Connick Jr. | 69 |
| 9 | Ray Charles | 60 |
| 10 | Etta James | 59 |
| 11 | Karen Souza | 49 |
| 12 | Jamie Cullum | 42 |
| 13 | Peggy Lee | 41 |
| 14 | Nina Simone | 39 |
| 15 | Sammy Davis Jr. | 39 |
| 16 | Sarah Vaughan | 38 |
| 17 | Al Jarreau | 36 |
| 18 | Dinah Washington | 32 |
| 19 | Nancy Wilson | 32 |
| 20 | Stacey Kent | 30 |