| 100% | WYNTONMARSALIS | 14 | First musician to win Grammy Awards for both a jazz and a classical recording |
| 41% | CARDIB | 6 | First woman to win a Grammy for Best Rap Album as a solo artist |
| 40% | CARDIB | 6 | First woman to win a Grammy for Best Rap Album as a solo artist (2 wds.) |
| 40% | MARSALIS | 8 | First jazz musician to win a Pulitzer Prize |
| 40% | NKJEMISIN | 9 | First author to win a Hugo Award for every book in a trilogy |
| 37% | WHOOPI | 6 | ___ Goldberg, comedian who won a Grammy Award for Best Comedy Recording in 1986 |
| 37% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 36% | BASIE | 5 | Jazz great who was the first African-American man to win a Grammy |
| 36% | JONI | 4 | ___ Mitchell, multiple Grammy-winning singer-songwriter and the first female musician to become a Companion of the Order of Canada |
| 36% | BAHA | 4 | ___ Men (group that won a Grammy Award in 2001 for Best Dance Recording) |
| 36% | BEY | 3 | Queen ___ (nickname for the artist who has won a record 32 Grammy Awards) |
| 36% | BLUE | 4 | "___ (Da Ba Dee)" a hit song by Eiffel 65 that won a Grammy award for "Best Dance Recording" |
| 36% | CARDI | 5 | ___ B, hip hop star who became the first female rapper to win a Grammy for Best Rap Album |
| 35% | CAROLEKING | 10 | "You've Got a Friend" singer/pianist who was the first woman to win a Grammy for Song of the Year (2 wds.) |
| 35% | DIAHANNCARROLL | 14 | First Black performer to win a Tony Award for Lead Actress in a Musical, for "No Strings" in 1962: 2 wds. |
| 35% | SCHINDLERSLIST | 14 | 1993 film for which 46-Across won a Grammy Award and an Oscar (2 wds.) |
| 35% | GEORGSOLTI | 10 | Hungarian-British artist who holds the record for the most Grammy Awards won in a lifetime, with 31: 2 wds. |
| 35% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 35% | MYA | 3 | One-named singer who won a Grammy Award with Pink, Lil' Kim, and Christina Aguilera for "Lady Marmalade" |
| 35% | SOUL | 4 | Pixar film about a jazz musician that won the 2021 Annie Award for Best Animated Feature |
| 35% | MARY | 4 | ___ Martin, first Broadway actress to win a Tony Award for playing someone of the opposite sex |
| 35% | HARLANCOBEN | 11 | 17-Across and 30-Across novelist who is the first writer to win an Anthony Award, a Shamus Award, and an Edgar Award (2 wds.) |
| 35% | JAMESEARLJONES | 14 | First Black performer to win a Tony Award for Lead Actor in a Play, for "The Great White Hope" in 1969: 3 wds. |
| 34% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 34% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 34% | PHYLICIARASHAD | 14 | First Black performer to win a Tony Award for Lead Actress in a Play, for "A Raisin in the Sun" in 2004: 2 wds. |
| 34% | ADELE | 5 | First songwriter to win an Oscar for a James Bond theme |
| 34% | SALESMAN | 8 | "Death of a ___," first ever play to win a Tony Award for Best Production in four different years |
| 34% | SERIAL | 6 | First podcast to win a Peabody Award (2015) |
| 33% | PERCYFAITH | 10 | Bandleader/orchestrator whose instrumental version of "Theme from 'A Summer Place'" won a Grammy Award for Record of the Year in 1961 (2 wds.) |