| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 603 |
| 2 | Postmodern Jukebox | 235 |
| 3 | Dean Martin | 219 |
| 4 | Richard Cheese | 206 |
| 5 | Ella Fitzgerald | 194 |
| 6 | Bobby Darin | 107 |
| 7 | Billie Holiday | 79 |
| 8 | Brian Setzer | 47 |
| 9 | The Andrews Sisters | 44 |
| 10 | Jamie Cullum | 42 |
| 11 | Peggy Lee | 40 |
| 12 | Caro Emerald | 39 |
| 13 | Sammy Davis Jr. | 39 |
| 14 | Adriano Celentano | 32 |
| 15 | Louis Armstrong | 30 |
| 16 | The Puppini Sisters | 28 |
| 17 | Louis Prima | 27 |
| 18 | Johnny Mercer | 25 |
| 19 | Cole Porter | 20 |
| 20 | Steve Lawrence | 19 |