| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 606 |
| 2 | Michael Bublé | 303 |
| 3 | Engelbert Humperdinck | 226 |
| 4 | Dean Martin | 219 |
| 5 | Ella Fitzgerald | 195 |
| 6 | Tony Bennett | 150 |
| 7 | Nat King Cole | 138 |
| 8 | Brenda Lee | 108 |
| 9 | Andy Williams | 106 |
| 10 | Bobby Darin | 104 |
| 11 | Diana Krall | 103 |
| 12 | Bing Crosby | 92 |
| 13 | Johnny Mathis | 88 |
| 14 | Glen Campbell | 84 |
| 15 | Natalie Cole | 81 |
| 16 | Billie Holiday | 79 |
| 17 | Perry Como | 76 |
| 18 | The Drifters | 74 |
| 19 | Connie Francis | 73 |
| 20 | The Everly Brothers | 70 |