| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 677 |
| 2 | Michael Bublé | 313 |
| 3 | Dean Martin | 232 |
| 4 | Cliff Richard | 226 |
| 5 | Kelly Clarkson | 212 |
| 6 | Ella Fitzgerald | 208 |
| 7 | Tony Bennett | 164 |
| 8 | Mariah Carey | 163 |
| 9 | Nat King Cole | 162 |
| 10 | Josh Groban | 125 |
| 11 | Andy Williams | 120 |
| 12 | Brenda Lee | 114 |
| 13 | Shakin' Stevens | 114 |
| 14 | The Carpenters | 110 |
| 15 | Johnny Mathis | 99 |
| 16 | Bing Crosby | 98 |
| 17 | Amy Grant | 91 |
| 18 | Perry Como | 90 |
| 19 | Harry Connick Jr. | 68 |
| 20 | José Feliciano | 58 |