| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 659 |
| 2 | Dean Martin | 226 |
| 3 | Ella Fitzgerald | 201 |
| 4 | Tony Bennett | 162 |
| 5 | Bobby Darin | 109 |
| 6 | Billie Holiday | 79 |
| 7 | Harry Connick Jr. | 68 |
| 8 | Doris Day | 54 |
| 9 | Peggy Lee | 45 |
| 10 | The Andrews Sisters | 44 |
| 11 | Sammy Davis Jr. | 42 |
| 12 | Wayne Newton | 32 |
| 13 | Louis Prima | 32 |
| 14 | Louis Armstrong | 31 |
| 15 | Daniel Boaventura | 29 |
| 16 | Al Jolson | 28 |
| 17 | Mel Tormé | 27 |
| 18 | Rosemary Clooney | 27 |
| 19 | Johnny Mercer | 25 |
| 20 | Cole Porter | 24 |