| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 609 |
| 2 | Dean Martin | 219 |
| 3 | Ella Fitzgerald | 194 |
| 4 | Tony Bennett | 149 |
| 5 | Bobby Darin | 102 |
| 6 | Billie Holiday | 78 |
| 7 | Harry Connick Jr. | 68 |
| 8 | Doris Day | 50 |
| 9 | The Andrews Sisters | 43 |
| 10 | Peggy Lee | 40 |
| 11 | Sammy Davis Jr. | 39 |
| 12 | Wayne Newton | 32 |
| 13 | Louis Armstrong | 31 |
| 14 | Louis Prima | 28 |
| 15 | Al Jolson | 27 |
| 16 | Mel Tormé | 26 |
| 17 | Daniel Boaventura | 26 |
| 18 | Johnny Mercer | 25 |
| 19 | Cole Porter | 24 |
| 20 | Rosemary Clooney | 22 |