| 100% | NORAH | 5 | With 32-Across, "Come Away With Me" singer who won five Grammy Awards in 2003 |
| 63% | NORAH | 5 | With 22-Down, "Come Away with Me" singer who won the 2002 Best New Artist Grammy Award |
| 56% | ALISONKRAUSS | 12 | "Raising Sand" singer who won five Grammy Awards in 2009: 2 wds. |
| 56% | AMYWINEHOUSE | 12 | "Back to Black" singer who won five Grammy Awards in 2008: 2 wds. |
| 53% | EILISH | 6 | Billie ___, singer who won five Grammy awards including Record of the Year in 2020 |
| 53% | MILEY | 5 | With 32-Across, singer-songwriter who exclaimed "I just won my first Grammy!" during her performance of "Flowers" at the 2024 Grammy Awards |
| 51% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 47% | BILLIEEILISH | 12 | "Bad Guy" singer who won a record five Grammy Awards in 2020, including Best New Artist (2 wds.) |
| 46% | SAMSMITH | 8 | "Stay With Me" singer who won 14-Across in 2015: 2 wds. |
| 46% | NORAH | 5 | Grammy-winning “Come Away with Me” singer Jones |
| 46% | LEANN | 5 | With 33-Across, "Blue" singer who won the Best New Artist Grammy in 1997 |
| 45% | BILLIE | 6 | With 34-Across, "Bad Guy" singer who won a Best New Artist Grammy in 2020 |
| 45% | DAVID | 5 | ___ Bowie, English singer who won a Grammy Award for best music video in 1985 |
| 44% | OLIVIA | 6 | ___ Rodrigo, "Drivers License" singer who won the Grammy Award for Best New Artist in 2022 |
| 44% | JON | 3 | ___ Batiste, "We Are" singer who won the Grammy Award for Album of the Year in 2022 |
| 44% | SMOKEYROBINSON | 14 | "I Second That Emotion" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 44% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 43% | ROSS | 4 | Diana ___, American singer who won a Grammy for lifetime achievement award in 2012 |
| 43% | ETTA | 4 | Singer James honored with a Grammy Lifetime Achievement Award in 2003 |
| 43% | MYA | 3 | One-named singer who won a Grammy Award with Pink, Lil' Kim, and Christina Aguilera for "Lady Marmalade" |
| 42% | BADBUNNY | 8 | "Dákiti" singer who won five Billboard Music Awards, including Top Latin Artist, in 2021 (2 wds.) |
| 42% | ALJARREAU | 9 | Singer who won Grammy Awards in three different categories (jazz, pop, and R. & B.) |
| 42% | SARABAREILLES | 13 | "Love Song" singer/pianist who performed a duet with 18-Across at the Grammy Awards in 2014 (2 wds.) |
| 41% | OSLIN | 5 | Arkansas-born country singer K.T. ___, who won a Grammy in 1989 for "Hold Me" |
| 41% | POPSMOKE | 8 | "What You Know Bout Love" singer who won five Billboard Music Awards, including Top New Artist, in 2021 (2 wds.) |
| 40% | NEIL | 4 | With 15-Across, "How I Met Your Mother" actor who won a 2014 Tony Award for starring in "Hedwig and the Angry Inch" |
| 40% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 40% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 40% | NORAH | 5 | Singer Come Away With Me, Jones |
| 40% | SEAL | 4 | Singer who won three Grammy Awards for "Kiss from a Rose" |