| 100% | ADELE | 5 | English singer-songwriter who won Grammy Awards for "25" and 14-Across |
| 73% | PEABOBRYSON | 11 | Singer/songwriter who won Grammy Awards for 34-Across and the "Beauty and the Beast" theme (2 wds.) |
| 54% | ADELE | 5 | One-named singer who won Grammys for "25" and 14-Across |
| 51% | ALJARREAU | 9 | Singer who won Grammy Awards in three different categories (jazz, pop, and R. & B.) |
| 51% | CARLY | 5 | Singer/songwriter Simon who won a Grammy and an Oscar for "Let the River Run" |
| 50% | ERICA | 5 | Singer Campbell who won a Best Gospel Album Grammy Award for "Help" |
| 49% | MYA | 3 | One-named singer who won a Grammy Award with Pink, Lil' Kim, and Christina Aguilera for "Lady Marmalade" |
| 49% | DAVID | 5 | ___ Bowie, English singer who won a Grammy Award for best music video in 1985 |
| 49% | ADELE | 5 | English singer who won the Academy Award for Best Original Song for the movie "Skyfall" |
| 48% | SEAL | 4 | Singer who won three Grammy Awards for "Kiss from a Rose" |
| 47% | SMITH | 5 | Sam ___, English singer who won the Academy Award for Best Original Song for the movie "Spectre" |
| 46% | ADELE | 5 | Singer who won a Grammy Award for Song of the Year winner for "Hello" |
| 45% | CHRISSTAPLETON | 14 | "Starting Over" singer/songwriter who won the 2021 CMA Awards for Male Vocalist of the Year, Album of the Year, Single of the Year, and Song of the Year (2 wds.) |
| 44% | TBONEBURNETT | 12 | Music legend who produced 14-Across and won a 2007 Grammy for Robert Plant and 47-Across's first collaboration, "Raising Sand" (3 wds.) |
| 44% | WYNTONMARSALIS | 14 | First musician to win Grammy Awards for both a jazz and a classical recording |
| 44% | ADELE | 5 | British singer-songwriter who won six prizes at the 2012 Grammy Awards |
| 44% | JOEL | 4 | Actor/singer Grey who won a Tony Award and an Oscar for "Cabaret" |
| 44% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 44% | MARS | 4 | Singer Bruno who won six 2017 Grammy Awards |
| 44% | SOUNDGARDEN | 11 | Grunge rock band who won the 1995 Best Hard Rock Performance Grammy for 14-Across |
| 43% | MANN | 4 | Singer Aimee who won the Grammy for "Mental Illness" |
| 43% | ENYA | 4 | Singer who won a Best New Age Album Grammy Award for "Amarantine" |
| 43% | ELLA | 4 | Jazz great Fitzgerald who won 14 Grammy Awards |
| 42% | ROSS | 4 | Diana ___, American singer who won a Grammy for lifetime achievement award in 2012 |
| 42% | KACEY | 5 | Singer Musgraves who won a 2013 Grammy for Best Country Album |
| 42% | RAITT | 5 | Singer Bonnie who won a Grammy for "Something to Talk About" |
| 42% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 42% | TAYLORSWIFT | 11 | "Love Story" singer-songwriter who won the award for Top Female Artist in Billboard 2018: 2 wds. |
| 42% | CARA | 4 | Singer Alessia who won Best New Artist at the 2018 Grammy Awards |
| 42% | CHER | 4 | American singer and actress who won the Academy Award for Best Actress for the romantic comedy "Moonstruck" |