| # | Artist | Songs |
|---|---|---|
| 1 | Frank Sinatra | 677 |
| 2 | Willie Nelson | 259 |
| 3 | Barbra Streisand | 241 |
| 4 | Dean Martin | 238 |
| 5 | Ella Fitzgerald | 207 |
| 6 | Julio Iglesias | 170 |
| 7 | Bing Crosby | 98 |
| 8 | Crystal Gayle | 87 |
| 9 | Connie Francis | 82 |
| 10 | Doris Day | 56 |
| 11 | Sammy Davis Jr. | 44 |
| 12 | Jerry Vale | 43 |
| 13 | The Platters | 36 |
| 14 | Tony Christie | 32 |
| 15 | Mitch Miller | 30 |
| 16 | Frankie Laine | 29 |
| 17 | Al Jolson | 29 |
| 18 | Patti Page | 28 |
| 19 | Mel Tormé | 27 |
| 20 | Howard Keel | 27 |