| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 654 |
| 2 | Michael Bublé | 308 |
| 3 | Dean Martin | 228 |
| 4 | Cliff Richard | 222 |
| 5 | Kelly Clarkson | 208 |
| 6 | Ella Fitzgerald | 203 |
| 7 | Tony Bennett | 164 |
| 8 | Mariah Carey | 162 |
| 9 | Nat King Cole | 160 |
| 10 | Josh Groban | 120 |
| 11 | Andy Williams | 116 |
| 12 | Brenda Lee | 112 |
| 13 | Shakin' Stevens | 110 |
| 14 | The Carpenters | 107 |
| 15 | Bing Crosby | 97 |
| 16 | Johnny Mathis | 97 |
| 17 | Amy Grant | 89 |
| 18 | Perry Como | 88 |
| 19 | Harry Connick Jr. | 68 |
| 20 | José Feliciano | 58 |