| 100% | ADELE | 5 | One-named singer who won Grammys for "25" and 14-Across |
| 58% | ADELE | 5 | English singer-songwriter who won Grammy Awards for "25" and 14-Across |
| 58% | MYA | 3 | One-named singer who won a Grammy Award with Pink, Lil' Kim, and Christina Aguilera for "Lady Marmalade" |
| 54% | MARS | 4 | Singer Bruno who won Grammys for Record, Album, and Song of the Year in 2018 |
| 54% | HER | 3 | One-named singer who won the Academy Award for Best Original Song in 2021 for "Fight for You" from the film "Judas and the Black Messiah" |
| 50% | ENYA | 4 | One-named singer who has won four Best New Age Album Grammys |
| 49% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 48% | BECK | 4 | Jeff ___, guitarist who won Grammys for performing songs like "Plan B" and "Dirty Mind" |
| 47% | ZAYN | 4 | "Pillowtalk" singer who won the Billboard Music Award for New Artist of the Year as a member of One Direction in 2013 and as a solo artist in 2017 |
| 47% | LEXICOGRAPHERS | 14 | Ones who produced the clues for 20-, 25- and 45-Across |
| 46% | ENYA | 4 | One-named Irish singer who has won four Best New Age Album Grammys |
| 46% | STEVIEWONDER | 12 | "Superstition" singer who has won 25 Grammys: 2 wds. |
| 45% | ETTA | 4 | Singer ___ James who's won blues and jazz Grammys |
| 45% | KACEYMUSGRAVES | 14 | 19-Across and 46-Across singer who won four 2019 Grammys, including Album of the Year and Best Country Album for "Golden Hour" (2 wds.) |
| 44% | LORDE | 5 | "Royals" singer who won 14-Across in 2014 |
| 44% | DANGELO | 7 | One-named R&B singer who won a Grammy for his 2014 album "Black Messiah" |
| 44% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 44% | PEABOBRYSON | 11 | Singer/songwriter who won Grammy Awards for 34-Across and the "Beauty and the Beast" theme (2 wds.) |
| 43% | THUNDERCAT | 10 | Former Suicidal Tendencies bassist who won two Grammys as a solo act, for the hit song "These Walls" and the album 28-Across |
| 43% | CYNDI | 5 | Singer Lauper who has won an Emmy, a Tony, and two Grammys |
| 43% | ADELE | 5 | One-named singer who won the 2016 Album of the Year |
| 43% | FETTYWAP | 8 | "Trap Queen" singer who won 14-Across in 2016: 2 wds. |
| 43% | ENYA | 4 | One-named singer who speaks English and Gaelic |
| 42% | SAMSMITH | 8 | "Stay With Me" singer who won 14-Across in 2015: 2 wds. |
| 42% | AMYWINEHOUSE | 12 | British singer who won five Grammys in 2008, including Best New Artist, and died of alcohol poisoning in 2011: 2 wds. |
| 42% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 42% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 42% | RACHAELRAY | 10 | Chef who won two Emmys for Outstanding Talk Show and one for Outstanding Service Show (2 wds.) |
| 42% | NICO | 4 | One-named singer who was a muse for Andy Warhol |
| 41% | ADELE | 5 | Singer who won an Oscar for "Skyfall" |