| # | Artist | Songs | 
|---|---|---|
| 1 | Frank Sinatra | 27 | 
| 2 | Nat King Cole | 18 | 
| 3 | Tony Bennett | 12 | 
| 4 | Anne Wilson | 9 | 
| 5 | Judy Collins | 9 | 
| 6 | Joan Baez | 8 | 
| 7 | Perry Como | 8 | 
| 8 | Johnny Mathis | 7 | 
| 9 | Andy Williams | 6 | 
| 10 | The Duprees | 6 | 
| 11 | Johnny Hartman | 5 | 
| 12 | Barbra Streisand | 4 | 
| 13 | Dean Martin | 4 | 
| 14 | Doris Day | 4 | 
| 15 | Julie London | 4 | 
| 16 | Paul Anka | 4 | 
| 17 | Queen Latifah | 4 | 
| 18 | The Marvelettes | 4 | 
| 19 | Walter Jackson | 4 | 
| 20 | Zach Williams | 4 |