| 100% | EMINEM | 6 | 16-Across, 21-Across, and 42-Across rapper who has won 15 Grammy Awards from 44 nominations |
| 38% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 38% | RIHANNA | 7 | Barbadian singer of "Unfaithful" fame who has won multiple Grammy awards and has a statue at Madame Tussauds, London |
| 38% | SHAKIRA | 7 | Colombian singer of "El Dorado" fame who has won multiple Grammy awards and has a statue at Madame Tussauds, Hollywood |
| 38% | MENATWORK | 9 | 15-Across and 33-Across rock band from Australia that won Best New Artist at the 1983 Grammy Awards (3 wds.) |
| 37% | KANYEWEST | 9 | Rapper/record producer who has won the second-most Grammy Awards among rappers (2 wds.) |
| 37% | JOHNWILLIAMS | 12 | Film music composer who has won 24 Grammy Awards, five Oscars, and four Golden Globes in the last six decades (2 wds.) |
| 37% | SNOOPDOGG | 9 | "Drop It Like It's Hot" rapper who has never won a Grammy despite 17 nominations: 2 wds. |
| 36% | MENATWORK | 9 | Australian rock band who sang 15-Across and 33-Across and won Best New Artist at the 1983 Grammy Awards (3 wds.) |
| 36% | ART | 3 | Singer ___ Garfunkel who has won eight Grammy Awards |
| 36% | ENYA | 4 | New Age vocalist who has won four Grammy Awards |
| 35% | LILWAYNE | 8 | "Lollipop" rapper who's won five Grammy Awards: 2 wds. |
| 34% | ROCK | 4 | Chris ___, comedian who has won three Grammy Awards for his comedy albums |
| 34% | NORAHJONES | 10 | "Don't Know Why" singer who has won nine Grammy Awards (2 wds.) |
| 34% | JAY | 3 | ___ Z, American rapper who has received 77 Grammy nominations |
| 34% | KANYE | 5 | Rapper West who has won 21 Grammys |
| 34% | ALISONKRAUSS | 12 | Bluegrass singer born July 23, 1971, who has won 27 Grammy Awards (2 wds.) |
| 34% | CARTER | 6 | Jimmy ___, US President who has won three Grammy awards for Best Spoken Word Album |
| 34% | BARACK | 6 | ___ Obama, US President who has won two Grammy awards for Best Spoken Word Album |
| 34% | KANYE | 5 | Rapper West who has had 69 Grammy nominations |
| 33% | ADELE | 5 | English singer-songwriter who won Grammy Awards for "25" and 14-Across |
| 33% | WILL | 4 | ___ Smith, actor and rapper who has won 4 Grammys as of 2021 |
| 33% | NNEDIOKORAFOR | 13 | 15-Across and 32-Across novelist who won a Hugo Award and a Nebula Award for "Binti" (2 wds.) |
| 32% | JULIANFELLOWES | 14 | 18-Across and 44-Across writer/creator who won an Academy Award for Best Original Screenplay for "Gosford Park" (2 wds.) |
| 32% | MEL | 3 | Brooks who has won an Oscar, Emmy, Grammy and Tony |
| 32% | MEL | 3 | Brooks who has won the Emmy, Oscar, Tony, and Grammy |
| 32% | ART | 3 | I am Garfunkel of the "Simon & Garfunkel" duo and I have won eight Grammy Awards |
| 32% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 32% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 32% | JONES | 5 | Quincy ___, American songwriter and composer who has received 80 Grammy nominations |