| 100% | FRANKSINATRA | 12 | Singer and actor for whom Paul Anka wrote the hit song "My Way": 2 wds. |
| 46% | SARABAREILLES | 13 | "Love Song" singer who wrote the music and lyrics for the Broadway musical "Waitress": 2 wds. |
| 44% | PAULANKA | 8 | Canadian singer/songwriter known for the hit songs "Diana" and "Put Your Head on My Shoulder" (2 wds.) |
| 42% | ANKA | 4 | Singer/songwriter Paul who wrote the memoir (and the song) "My Way" |
| 41% | ANKA | 4 | Singer-songwriter Paul who wrote the memoir (and the song) "My Way" |
| 41% | DOLLYPARTON | 11 | "Jolene" singer who wrote the music and lyrics for the Broadway musical "9 to 5": 2 wds. |
| 40% | BRYANADAMS | 10 | Canadian singer known for the hit songs "Summer of '69" and "Heaven" (2 wds.) |
| 40% | PAULMCCARTNEY | 13 | Singer and bass guitarist for the Beatles who was knighted in 1997: 2 wds. |
| 39% | JENNIFERLOPEZ | 13 | American singer and actress who has made hits like "On the Floor": 2 wds. |
| 38% | SARABAREILLES | 13 | Singer-songwriter who wrote music and lyrics for the stage adaptation of the film "Waitress" (2 wds.) |
| 37% | SARABAREILLES | 13 | Singer/songwriter who wrote music and lyrics for the stage adaptation of "Waitress" (2 wds.) |
| 36% | CYNDILAUPER | 11 | "Time After Time" singer who wrote the music and lyrics for the Broadway musical "Kinky Boots": 2 wds. |
| 36% | ANKA | 4 | Singer-songwriter Paul who wrote "My Way" and "Diana" |
| 36% | BLUEBAYOU | 9 | Top 5 hit song for 33-Across written by Roy Orbison and Joe Melson (2 wds.) |
| 35% | TIMMCGRAW | 9 | American country singer and actor from "The Blind Side" who holds a pilot license and owns a Cirrus SR22: 2 wds. |
| 35% | IRVINGBERLIN | 12 | Composer who wrote the songs for 17-Across (2 wds.) |
| 35% | LESLIEODOMJR | 12 | "One Night in Miami" singer/actor who was nominated for Oscars for Best Supporting Actor and for Best Original Song (3 wds.) |
| 35% | STEVEMARTIN | 11 | "The Pink Panther" actor who wrote the kids' book "Late for School": 2 wds. |
| 35% | SMITH | 5 | Patti ___, singer and songwriter who wrote the song "Dancing Barefoot" |
| 35% | LONELYTONIGHT | 13 | 2014 hit song for 17- and 39-Across: 2 wds. |
| 34% | CHANNINGTATUM | 13 | "Magic Mike" actor who wrote the children's book "The One and Only Sparkella": 2 wds. |
| 34% | MARIEOSMOND | 11 | Singer and talk show host who has been a spokesperson for Nutrisystem: 2 wds. |
| 34% | OHCAROL | 7 | Neil Sedaka's hit song written for musician behind "Tapestry": 2 wds. |
| 34% | STEVIEWONDER | 12 | "Piano man" with the hit song "My Cherie Amour": 2 wds. |
| 33% | TOBYKEITH | 9 | Singer (with Willie Nelson) of the 2003 song "Beer for My Horses": 2 wds. |
| 33% | MRT | 3 | Retired professional wrestler and actor who starred in "I Pity the Fool": 2 wds. |
| 33% | SARA | 4 | Singer Bareilles who wrote and composed the music for Broadway's "Waitress" |
| 33% | OCASEK | 6 | Ric who wrote the hit song "My Best Friend's Girl" |
| 33% | ITSSOEASY | 9 | Top 5 hit song for 33-Across written by Buddy Holly and Norman Petty (3 wds.) |
| 33% | WONDER | 6 | Stevie ___ and Paul McCartney, singers who collaborated on the hit song "Ebony and Ivory" |