| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 606 |
| 2 | Dean Martin | 219 |
| 3 | Ella Fitzgerald | 195 |
| 4 | Tony Bennett | 150 |
| 5 | Nat King Cole | 138 |
| 6 | Bobby Darin | 104 |
| 7 | Diana Krall | 103 |
| 8 | Johnny Mathis | 88 |
| 9 | Aretha Franklin | 83 |
| 10 | Natalie Cole | 81 |
| 11 | Billie Holiday | 79 |
| 12 | Perry Como | 76 |
| 13 | Norah Jones | 72 |
| 14 | Harry Connick Jr. | 69 |
| 15 | Ray Charles | 60 |
| 16 | James Brown | 59 |
| 17 | Etta James | 59 |
| 18 | Dionne Warwick | 50 |
| 19 | Doris Day | 50 |
| 20 | Karen Souza | 49 |