| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 678 |
| 2 | Postmodern Jukebox | 252 |
| 3 | Dean Martin | 238 |
| 4 | Richard Cheese | 208 |
| 5 | Ella Fitzgerald | 207 |
| 6 | Bobby Darin | 114 |
| 7 | Billie Holiday | 79 |
| 8 | Brian Setzer | 49 |
| 9 | Peggy Lee | 47 |
| 10 | The Andrews Sisters | 45 |
| 11 | Sammy Davis Jr. | 44 |
| 12 | Jamie Cullum | 44 |
| 13 | Caro Emerald | 40 |
| 14 | Louis Armstrong | 34 |
| 15 | Louis Prima | 30 |
| 16 | Adriano Celentano | 30 |
| 17 | The Puppini Sisters | 30 |
| 18 | Johnny Mercer | 25 |
| 19 | Cole Porter | 24 |
| 20 | Steve Lawrence | 22 |