| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 659 |
| 2 | Postmodern Jukebox | 244 |
| 3 | Dean Martin | 226 |
| 4 | Richard Cheese | 211 |
| 5 | Ella Fitzgerald | 201 |
| 6 | Bobby Darin | 109 |
| 7 | Billie Holiday | 79 |
| 8 | Brian Setzer | 48 |
| 9 | Peggy Lee | 45 |
| 10 | The Andrews Sisters | 44 |
| 11 | Jamie Cullum | 43 |
| 12 | Sammy Davis Jr. | 42 |
| 13 | Caro Emerald | 40 |
| 14 | Adriano Celentano | 33 |
| 15 | Louis Prima | 32 |
| 16 | Louis Armstrong | 31 |
| 17 | The Puppini Sisters | 28 |
| 18 | Johnny Mercer | 25 |
| 19 | Cole Porter | 24 |
| 20 | Steve Lawrence | 23 |