| 100% | NEILDIAMOND | 11 | "Song Sung Blue" singer who will no longer tour due to Parkinson's disease, but still plans to write and record music: 2 wds. |
| 32% | JENNIFERLOPEZ | 13 | Singer who was nominated for a Grammy for Best Dance Recording in 2000 but lost to Cher: 2 wds. |
| 32% | SARABAREILLES | 13 | "Love Song" singer who wrote the music and lyrics for the Broadway musical "Waitress": 2 wds. |
| 31% | DOLLYPARTON | 11 | "Jolene" singer who wrote the music and lyrics for the Broadway musical "9 to 5": 2 wds. |
| 30% | THECARPENTERS | 13 | Music group with siblings as members with hit songs like "(They Long to Be) Close to You" and "We've Only Just Begun": 2 wds. |
| 29% | IGGYAZALEA | 10 | "Fancy" singer who is one of only two music acts to have their first two hit singles rank #1 and #2 simultaneously on the U.S. "Billboard" Hot 100 chart (2 wds.) |
| 29% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 29% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |
| 29% | CALVINHARRIS | 12 | Rihanna's longest-running number one single "We Found Love" was written by ___, famed Scottish DJ, singer and songwriter: 2 wds. |
| 28% | PAULMCCARTNEY | 13 | Beatles bassist and singer who never learned to read music: 2 wds. |
| 28% | FRANKSINATRA | 12 | Singer and actor for whom Paul Anka wrote the hit song "My Way": 2 wds. |
| 28% | SELENAGOMEZ | 11 | "Hands to Myself" singer who records in both English and Spanish: 2 wds. |
| 28% | DIANAROSS | 9 | American singer who was the lead singer of "The Supremes" and is known for her solo songs like "Upside Down": 2 wds. |
| 28% | ANDRAECROUCH | 12 | "Soon and Very Soon" singer who was inducted into the Gospel Music Hall of Fame in 1998: 2 wds. |
| 28% | NOLANRYAN | 9 | Pitcher who had a record seven no-hitters and played to age 46, in 1993: 2 wds. |
| 28% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (2 wds.) |
| 28% | LINDARONSTADT | 13 | "You're No Good" singer who was inducted into the Rock and Roll Hall of Fame in 2014: 2 wds. |
| 28% | ETHELWATERS | 11 | Harlem Renaissance singer and actress who was the first African American to star in her own TV show: 2 wds. |
| 27% | ERICCLAPTON | 11 | English rock and blues guitarist who is the only artist to be inducted three times into the Rock and Roll Hall of Fame: 2 wds. |
| 27% | DREWBARRYMORE | 13 | American singer SZA's song which is titled after a "Charlie's Angels" actress who also makes a cameo in the music video: 2 wds. |
| 27% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was the first Black country artist to cohost the CMA Awards (1975) and the ACM Awards (1980): 2 wds. |
| 27% | LEONARDCOHEN | 12 | Canadian singer/songwriter who wrote and recorded 34-Across in 1984 (2 wds.) |
| 27% | CYNDILAUPER | 11 | "Time After Time" singer who wrote the music and lyrics for the Broadway musical "Kinky Boots": 2 wds. |
| 27% | COFFEESONG | 10 | "The ___," song written by Bob Hilliard and Dick Miles which was recorded by Frank Sinatra in 1946: 2 wds. |
| 27% | STEVIEWONDER | 12 | Singer who signed with record company Motown when he was 11 and gave his first number-one hit at 13: 2 wds. |
| 26% | BILLYJOEL | 9 | Singer whose 1980 "Glass Houses" album includes the #1 song "It's Still Rock and Roll to Me" (2 wds.) |
| 26% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 26% | 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.) |
| 26% | DIERKSBENTLEY | 13 | Singer of 15-Across and 29-Across who was honored with an Academy of Country Music's Merle Haggard Spirit Award (2 wds.) |
| 26% | PATSYCLINE | 10 | American singer (birthday today) who was the first female solo artist inducted to the Country Music Hall of Fame: 2 wds. |