| 100% | SINEADOCONNOR | 13 | Singer whose "Nothing Compares 2 U" was a #1 song for four weeks in 1990 (2 wds.) |
| 63% | JANETJACKSON | 12 | Singer whose "Escapade" was a #1 song for three weeks in 1990 (2 wds.) |
| 63% | ALANNAHMYLES | 12 | Singer whose "Black Velvet" was a #1 song for two weeks in 1990 (2 wds.) |
| 44% | TRACYCHAPMAN | 12 | Singer whose song "Fast Car," from her self-titled debut album, was a #6 hit in 1988: 2 wds. |
| 43% | PAULMCCARTNEY | 13 | Former Beatle whose Maracana Stadium concert in 1990 is the second highest-attended ticketed concert for a single artist: 2 wds. |
| 43% | TINATURNER | 10 | American singer whose Maracana Stadium concert in 1988 is the third highest-attended ticketed concert for a single artist: 2 wds. |
| 43% | VASCOROSSI | 10 | Italian singer whose Enzo Ferrari Park concert in 2017 is the highest-attended ticketed concert for a single artist: 2 wds. |
| 43% | BLUEBAYOU | 9 | Roy Orbison song that was a #3 hit for 32-Across in 1977: 2 wds. |
| 42% | KATYPERRY | 9 | Starting in 2010, pop singer with a song in the top 10 of the Billboard Hot 100 for 69 consecutive weeks: 2 wds. |
| 42% | THEWEEKND | 9 | Canadian singer whose "Blinding Lights" was the #1 song on Spotify in 2020: 2 wds. |
| 42% | LADYGAGA | 8 | Singer-songwriter whose song "Shallow" from the movie "A Star Is Born" won her an Oscar in 2018: 2 wds. |
| 41% | KILLBILL | 8 | 2022 SZA song that was #1 on the Hot R&B/Hip-Hop charts for 21 weeks, a record: 2 wds. |
| 41% | MILEYCYRUS | 10 | "Party in the U.S.A." singer whose first TV series lead role was on Disney's "Hannah Montana": 2 wds. |
| 41% | JLO | 3 | Singer whose "This Is Me ... Now" album dropped in 2024, for short: 2 wds. |
| 41% | KELLYCLARKSON | 13 | Singer whose hit single "Since U Been Gone" is featured in the Broadway musical "& Juliet" (2 wds.) |
| 41% | ALJARREAU | 9 | Singer whose "Moonlighting" was the theme song for the TV show of the same name: 2 wds. |
| 40% | SINEADOCONNOR | 13 | Singer with the 1990 hit "Nothing Compares 2 U": 2 wds. |
| 40% | LUKECOMBS | 9 | Country singer whose cover of 27-Across's "Fast Car" was a #2 hit in 2023: 2 wds. |
| 40% | IFEELFORYOU | 11 | Grammy-winning song written by Prince that was a #1 hit for Chaka Khan in 1984 (4 wds.) |
| 40% | RONALDREAGAN | 12 | 40th US president for whom a DC-area airport was renamed in 1998: 2 wds. |
| 40% | SINEADOCONNOR | 13 | "Nothing Compares 2 U" singer who rocked a shaved head: 2 wds. |
| 39% | CHRISBROWN | 10 | "Forever" singer featured on three songs in Billboard's top 10 during a week in 2008: 2 wds. |
| 39% | RALPHLAUREN | 11 | US fashion designer known for shirts whose logo is a polo pony and rider: 2 wds. |
| 39% | ASHANTI | 7 | Singer whose 2002 song "Foolish" was #1 for 10 weeks |
| 39% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 39% | LEANONME | 8 | Song that was a #1 hit for Bill Withers in 1972 and for Club Nouveau in 1987: 3 wds. |
| 39% | WITHOUTYOU | 10 | 2020 song by the Kid Laroi whose remix was a top 10 hit in 2021: 2 wds. |
| 39% | JOEYFATONE | 10 | Former 'N Sync singer whose first name is also the term for a baby kangaroo: 2 wds. |
| 39% | CRISTIEKERR | 11 | American golfer who was #1 in the LPGA for five weeks in 2010: 2 wds. |
| 39% | ANITABAKER | 10 | "Sweet Love" singer whose last name is a synonym for a pastry chef: 2 wds. |