| # | Artist | Songs |
|---|---|---|
| 1 | Dean Martin | 217 |
| 2 | Ella Fitzgerald | 194 |
| 3 | Tony Bennett | 145 |
| 4 | Nat King Cole | 133 |
| 5 | Diana Krall | 103 |
| 6 | Bobby Darin | 102 |
| 7 | Johnny Mathis | 86 |
| 8 | Aretha Franklin | 83 |
| 9 | Natalie Cole | 79 |
| 10 | Billie Holiday | 78 |
| 11 | Perry Como | 76 |
| 12 | Norah Jones | 72 |
| 13 | Harry Connick Jr. | 66 |
| 14 | Ray Charles | 60 |
| 15 | James Brown | 59 |
| 16 | Etta James | 58 |
| 17 | Doris Day | 49 |
| 18 | Dionne Warwick | 48 |
| 19 | Sam Cooke | 46 |
| 20 | The Andrews Sisters | 42 |