| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 609 |
| 2 | Dean Martin | 219 |
| 3 | Ella Fitzgerald | 194 |
| 4 | Tony Bennett | 149 |
| 5 | Nat King Cole | 134 |
| 6 | Diana Krall | 104 |
| 7 | Bobby Darin | 102 |
| 8 | Johnny Mathis | 86 |
| 9 | Aretha Franklin | 83 |
| 10 | Natalie Cole | 80 |
| 11 | Billie Holiday | 78 |
| 12 | Perry Como | 76 |
| 13 | Norah Jones | 72 |
| 14 | Harry Connick Jr. | 68 |
| 15 | James Brown | 59 |
| 16 | Ray Charles | 59 |
| 17 | Etta James | 58 |
| 18 | Doris Day | 50 |
| 19 | Karen Souza | 49 |
| 20 | Dionne Warwick | 48 |