| 100% | DREWBARRYMORE | 13 | Unexpected singer of "Way Back Into Love" in 2007's "Music and Lyrics" (with Hugh Grant): 2 wds. |
| 39% | PIERCEBROSNAN | 13 | Unexpected singer of "SOS" in 2008's "Mamma Mia!" (with Meryl Streep): 2 wds. |
| 37% | CHRISTIANBALE | 13 | Unexpected singer of "Santa Fe" in 1992's "Newsies": 2 wds. |
| 35% | ANDRAECROUCH | 12 | "Soon and Very Soon" singer who was inducted into the Gospel Music Hall of Fame in 1998: 2 wds. |
| 34% | ELVISPRESLEY | 12 | "Love Me Tender" singer who was inducted into the Gospel Music Hall of Fame in 2001: 2 wds. |
| 33% | TINATURNER | 10 | "What's Love Got to Do With It" singer inducted into the Rock and Roll Hall of Fame in 2021: 2 wds. |
| 33% | KENNYCHESNEY | 12 | Singer of the 2007 #1 country hit "Beer in Mexico": 2 wds. |
| 33% | DOLLYPARTON | 11 | "Jolene" singer who was inducted into the Country Music Hall of Fame in 1999: 2 wds. |
| 33% | SARABAREILLES | 13 | Singer/songwriter who wrote music and lyrics for the stage adaptation of "Waitress" (2 wds.) |
| 33% | LADYGAGA | 8 | Singer of the #1 hits "Just Dance" and "Born This Way": 2 wds. |
| 32% | LORETTALYNN | 11 | "Coal Miner's Daughter" singer who was inducted into the Country Music Hall of Fame in 1988: 2 wds. |
| 32% | TINATURNER | 10 | "What's Love Got to Do with It" singer nominated to the Rock and Roll Hall of Fame in 2021 (2 wds.) |
| 32% | PETERFRAMPTON | 13 | Singer of “I'm in You” and “Baby, I Love Your Way” |
| 32% | YOLANDAADAMS | 12 | "Already Alright" singer who was inducted into the Gospel Music Hall of Fame in 2017: 2 wds. |
| 31% | SARABAREILLES | 13 | Singer-songwriter who wrote music and lyrics for the stage adaptation of the film "Waitress" (2 wds.) |
| 31% | SARABAREILLES | 13 | Singer of the 2007 hit "Love Song": 2 wds. |
| 31% | DEBBIEHARRY | 11 | Lead singer of Blondie who received the first Billboard Women in Music Icon Award, in 2008: 2 wds. |
| 30% | SILKSTOCKINGS | 13 | 1955 Broadway show with music and lyrics by 41-Across: 2 wds. |
| 30% | ERICCLAPTON | 11 | "Layla" guitarist and singer who was inducted into the Rock and Roll Hall of Fame in 2000: 2 wds. |
| 30% | SARABAREILLES | 13 | "Love Song" singer who wrote the music and lyrics for the Broadway musical "Waitress": 2 wds. |
| 29% | DIERKSBENTLEY | 13 | Singer of 15-Across and 29-Across who was awarded the 2018 Academy of Country Music's Merle Haggard Spirit Award (2 wds.) |
| 29% | LINDARONSTADT | 13 | "You're No Good" singer who was inducted into the Rock and Roll Hall of Fame in 2014: 2 wds. |
| 29% | ANYTHINGGOES | 12 | 1934 show with music and lyrics by 39-Across whose 1987 and 2011 revivals both won the Tony Award for Best Revival of a Musical (2 wds.) |
| 29% | YEARSAGO | 8 | Way back in the past: 2 wds. |
| 29% | AGESAGO | 7 | Way back in the past: 2 wds. |
| 29% | MANDYMOORE | 10 | Singer of the hit 2000 single "I Wanna Be With You", who also voiced the role of Rapunzel in the animated film "Tangled": 2 wds. |
| 29% | ESTREETBAND | 11 | Longtime backing group for the Boss inducted into the Rock and Roll Hall of Fame in 2014: 3 wds. |
| 29% | ALLTOMYSELF | 11 | Dan + Shay song with the lyrics "I'm jealous of the song that you've been singin' / And the way it's rollin' off your lips" (3 wds.) |
| 29% | VANHALEN | 8 | David Lee Roth's band, inducted into the Rock and Roll Hall of Fame in 2007: 2 wds. |
| 29% | DIERKSBENTLEY | 13 | Singer of "Home" and 15-Across: 2 wds. |