| 100% | WINEHOUSE | 9 | Amy whose hit single "Rehab" won three Grammys |
| 55% | REHAB | 5 | Amy Winehouse hit that won three Grammys |
| 47% | HELLO | 5 | Adele hit song that won three Grammys |
| 46% | WINEHOUSE | 9 | Amy whose 2006 album "Back to Black" won five Grammys |
| 44% | HELLO | 5 | Adele hit that won three Grammys |
| 44% | REHAB | 5 | Amy Winehouse song that won three Grammys |
| 40% | ASIAM | 5 | 2007 Alicia Keys album that won three Grammys |
| 40% | REHAB | 5 | 2006 Amy Winehouse hit that won three Grammy Awards in 2008 |
| 39% | CELIA | 5 | Cruz who won three Grammys |
| 39% | RAWLS | 5 | Lou who won three Grammys |
| 39% | LOU | 3 | Singer Rawls who won three Grammys |
| 39% | ONO | 3 | Yoko who's won three Grammys |
| 37% | REM | 3 | Georgia band that won three Grammys in 1992 |
| 37% | JARS | 4 | ___ of Clay (Christian band that's won three Grammys) |
| 37% | SZA | 3 | “Kill Bill” singer who won three Grammys in 2024 |
| 36% | ANGELOU | 7 | Poet who won three Grammys for Best Spoken Word Album |
| 36% | RAITT | 5 | She won three Grammys for her 1989 album "Nick of Time" |
| 35% | VALDOONICAN | 11 | Irish entertainer whose hit singles included Walk Tall and Elusive Butterfly |
| 35% | ASHE | 4 | Arthur who won three Grand Slam singles titles |
| 34% | CHANCETHE | 9 | American singer-songwriter, ___ Rapper, who won three Grammys this year, including Best New Artist |
| 34% | BRANDI | 6 | ___ Carlile, "Broken Horses" female singer who won three Grammys at the 2023 Grammy Awards |
| 33% | RAITT | 5 | Bonnie ___, "Just Like That" female singer who won three Grammys at the 2023 Grammy Awards |
| 33% | EVERT | 5 | Chris with three Wimbledon singles wins |
| 33% | BRITNEYSPEARS | 13 | Singer whose hit single "Oops!... I Did It Again" is featured in "& Juliet" (2 wds.) |
| 33% | ELLIEGOULDING | 13 | Singer whose hit single "Love Me Like You Do" is featured in "& Juliet" (2 wds.) |
| 33% | OLIVIARODRIGO | 13 | Singer whose 2021 hit single "Drivers License" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 32% | VICARIO | 7 | Arantxa Sanchez ___, former tennis player who won three French Open singles titles |
| 32% | DOJACAT | 7 | Singer whose 2021 hit single "Kiss Me More" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 32% | SEAL | 4 | Single-named singer whose first hit was 1990's "Crazy" |