| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 609 |
| 2 | Postmodern Jukebox | 232 |
| 3 | Dean Martin | 219 |
| 4 | Richard Cheese | 207 |
| 5 | Ella Fitzgerald | 194 |
| 6 | Bobby Darin | 102 |
| 7 | Brian Setzer | 46 |
| 8 | The Andrews Sisters | 43 |
| 9 | Peggy Lee | 40 |
| 10 | Sammy Davis Jr. | 39 |
| 11 | Caro Emerald | 39 |
| 12 | Louis Armstrong | 31 |
| 13 | Louis Prima | 28 |
| 14 | The Puppini Sisters | 28 |
| 15 | Johnny Mercer | 25 |
| 16 | Cole Porter | 24 |
| 17 | Roger Cicero | 16 |
| 18 | Cherry Poppin' Daddies | 16 |
| 19 | Big Bad Voodoo Daddy | 16 |
| 20 | The Mills Brothers | 15 |