| # | Artist | Songs |
|---|---|---|
| 1 | Postmodern Jukebox | 233 |
| 2 | Ella Fitzgerald | 194 |
| 3 | Nat King Cole | 133 |
| 4 | Bing Crosby | 92 |
| 5 | Billie Holiday | 78 |
| 6 | Brian Setzer | 46 |
| 7 | The Andrews Sisters | 42 |
| 8 | Peggy Lee | 40 |
| 9 | Sammy Davis Jr. | 39 |
| 10 | Sarah Vaughan | 37 |
| 11 | Dinah Washington | 32 |
| 12 | Louis Armstrong | 30 |
| 13 | Louis Prima | 28 |
| 14 | The Puppini Sisters | 28 |
| 15 | Al Jolson | 27 |
| 16 | Mel Tormé | 26 |
| 17 | Johnny Mercer | 25 |
| 18 | Cole Porter | 24 |
| 19 | Rosemary Clooney | 22 |
| 20 | Big Bad Voodoo Daddy | 17 |