| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 604 |
| 2 | Michael Bublé | 298 |
| 3 | Engelbert Humperdinck | 225 |
| 4 | Dean Martin | 217 |
| 5 | Ella Fitzgerald | 194 |
| 6 | Tony Bennett | 145 |
| 7 | Nat King Cole | 133 |
| 8 | Andy Williams | 107 |
| 9 | Diana Krall | 103 |
| 10 | Bobby Darin | 102 |
| 11 | Brenda Lee | 101 |
| 12 | Bing Crosby | 92 |
| 13 | Johnny Mathis | 86 |
| 14 | Glen Campbell | 83 |
| 15 | Natalie Cole | 79 |
| 16 | Billie Holiday | 78 |
| 17 | Perry Como | 76 |
| 18 | Connie Francis | 72 |
| 19 | The Drifters | 71 |
| 20 | The Everly Brothers | 70 |