| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 659 |
| 2 | Willie Nelson | 244 |
| 3 | Barbra Streisand | 233 |
| 4 | Dean Martin | 226 |
| 5 | Ella Fitzgerald | 201 |
| 6 | Julio Iglesias | 167 |
| 7 | Bing Crosby | 91 |
| 8 | Connie Francis | 79 |
| 9 | Crystal Gayle | 78 |
| 10 | Doris Day | 54 |
| 11 | Jerry Vale | 43 |
| 12 | Sammy Davis Jr. | 42 |
| 13 | The Platters | 31 |
| 14 | Mitch Miller | 31 |
| 15 | Tony Christie | 30 |
| 16 | Frankie Laine | 29 |
| 17 | Al Jolson | 28 |
| 18 | Mel Tormé | 27 |
| 19 | Howard Keel | 25 |
| 20 | Michael Feinstein | 24 |