| 100% | ELLIEGOULDING | 13 | 15-Across and 29-Across singer whose hit single "Love Me Like You Do" was nominated for a Grammy Award (2 wds.) |
| 94% | ELLIEGOULDING | 13 | 14-Across and 45-Across singer whose hit single "Love Me Like You Do" was nominated for a Grammy Award (2 wds.) |
| 60% | ELLIEGOULDING | 13 | Singer whose hit single "Love Me Like You Do" is featured in "& Juliet" (2 wds.) |
| 56% | DOJACAT | 7 | Singer whose 2021 hit single "Kiss Me More" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 49% | OLIVIARODRIGO | 13 | Singer whose 2021 hit single "Drivers License" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 48% | PHOEBEBRIDGERS | 14 | 16-Across and 31-Across singer who was nominated for a 2020 Best New Artist Grammy Award (2 wds.) |
| 47% | BRANDICARLILE | 13 | Singer whose 2021 hit song "Right on Time" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 46% | LIVINGHISTORY | 13 | Memoir by 31-Across whose audiobook version was nominated for a Grammy Award for Best Spoken Word Album (2 wds.) |
| 45% | LILNASX | 7 | Singer whose 2021 hit song "Montero (Call Me by Your Name)" is nominated for three Grammy Awards, including Record of the Year (3 wds.) |
| 45% | WHITNEYHOUSTON | 14 | Singer and actress who played Rachel Marron in 18a and whose cover of "I Will Always Love You" became a best-selling single: 2 wds. |
| 45% | LUKASGRAHAM | 11 | Danish pop and soul band with the hit single "7 Years", that was nominated for Record of the Year in the 2017 Grammy Awards : 2 wds. |
| 44% | BRITNEYSPEARS | 13 | Singer whose hit single "Oops!... I Did It Again" is featured in "& Juliet" (2 wds.) |
| 44% | ELLIEGOULDING | 13 | "Love Me Like You Do" singer whose first and last names each start and end with the same letter: 2 wds. |
| 44% | BELIEVE | 7 | "I ___ in You," hit song by Australian singer Kylie Minogue which was nominated for a Grammy Award in 2006 |
| 43% | LOVESONG | 8 | Top 10 single by 31-Across that was nominated for two Grammy Awards (2 wds.) |
| 42% | DELREY | 6 | Singer Lana whose 2017 album "Lust for Life" was nominated for a Best Pop Vocal Album Grammy (2 wds.) |
| 42% | SIGHT | 5 | "Love at First ___," hit song by Australian singer Kylie Minogue which was nominated for a Grammy Award in 2003 |
| 42% | WHITNEYHOUSTON | 14 | "Saving All My Love for You" singer in the Rock and Roll Hall of Fame whose last name is a city in Texas (2 wds.) |
| 42% | ACTAFOOL | 8 | Single from Ludacris that was part of the soundtrack for "2 Fast 2 Furious," and was also nominated for a Grammy: 3 wds. |
| 41% | ADORE | 5 | "___ You," hit song by Harry Styles which was nominated for a Grammy award |
| 41% | SLOW | 4 | Hit song by Australian singer Kylie Minogue which was nominated for a Grammy Award in 2005 |
| 40% | FEELSLIKE | 9 | "___ Summer," hit song by Childish Gambino which was nominated for a Grammy: 2 wds. |
| 40% | JONIMITCHELL | 12 | 15-Across and 44-Across singer-songwriter who was honored with a Gershwin Award in 2023 (2 wds.) |
| 40% | MIDDLECHILD | 11 | J. Cole single from the album "Revenge of the Dreamers III" that was nominated for a Best Rap Performance Grammy Award in 2020 (2 wds.) |
| 40% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 40% | INDUSTRYBABY | 12 | 2021 #1 song by Lil Nas X and 36-Across that was nominated for a Best Melodic Rap Performance Grammy Award and won three MTV Video Music Awards (2 wds.) |
| 39% | NEEDTOKNOW | 10 | Hit single by 50-Across that was nominated for Best Melodic Rap Performance at the 2022 Grammy Awards (3 wds.) |
| 39% | BETTERNOW | 9 | Top 10 song by 42-Across that was nominated for a Best Pop Solo Performance Grammy Award (2 wds.) |
| 39% | JENNIFERLOPEZ | 13 | 15-Across and 27-Across singer who was the first woman honored with a "Billboard" Icon Award (2 wds) |
| 39% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |