| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 609 |
| 2 | Michael Bublé | 296 |
| 3 | Engelbert Humperdinck | 224 |
| 4 | Dean Martin | 219 |
| 5 | Ella Fitzgerald | 194 |
| 6 | Tony Bennett | 149 |
| 7 | Nat King Cole | 134 |
| 8 | Andy Williams | 107 |
| 9 | Brenda Lee | 106 |
| 10 | Diana Krall | 104 |
| 11 | Bobby Darin | 102 |
| 12 | Bing Crosby | 92 |
| 13 | Johnny Mathis | 86 |
| 14 | Glen Campbell | 84 |
| 15 | Natalie Cole | 80 |
| 16 | Billie Holiday | 78 |
| 17 | Perry Como | 76 |
| 18 | The Drifters | 75 |
| 19 | The Everly Brothers | 72 |
| 20 | Connie Francis | 72 |