| 100% | MIRANDALAMBERT | 14 | "Wildcard" Best Country Album Grammy winner who was born on November 10, 1983 (2 wds.) |
| 61% | DIANAKRALL | 10 | "When I Look in Your Eyes" Best Jazz Vocal Album Grammy winner who was born on November 16, 1964 (2 wds.) |
| 44% | GIUSEPPEVERDI | 13 | Italian composer who was born on October 10, 1813: 2 wds. |
| 44% | MILEYCYRUS | 10 | "Flowers" Record of the Year Grammy nominee who was born on November 23, 1992 (2 wds.) |
| 40% | JOHNLEGEND | 10 | "Ordinary People" Grammy winner who is a coach on season 25 of "The Voice" (2 wds.) |
| 40% | CARLOSSANTANA | 13 | Ten-time Grammy winner who was born July 20, 1947 (2 wds.) |
| 39% | DANANDSHAY | 10 | "Tequila" Grammy winners who are coaches on season 25 of "The Voice" (2 wds.) |
| 39% | CLAUDEMONET | 11 | "Impression, Sunrise" painter who was born in Paris on November 14, 1840: 2 wds. |
| 38% | TRAVISSCOTT | 11 | Rapper who was nominated for a Grammy for Best Rap Album in 2019 but lost to Cardi B: 2 wds. |
| 38% | REBAMCENTIRE | 12 | "Sing It Now: Songs of Faith & Hope" Grammy winner who is a coach on season 25 of "The Voice" (2 wds.) |
| 38% | JANELLEMONAE | 12 | Actress in the Best Picture winner "Moonlight" who was nominated for an Album of the Year Grammy in 2019: 2 wds. |
| 38% | RICHARDHARRIS | 13 | Actor in the Best Picture winner "Unforgiven" who was nominated for an Album of the Year Grammy in 1968: 2 wds. |
| 38% | MARIAHCAREY | 11 | Five-time Grammy winner who is the only artist whose first five singles reached #1 on the Billboard Hot 100 (2 wds.) |
| 38% | HENRYCAVILL | 11 | 18-Across, 24-Across, and 33-Across star who was born on May 5, 1983 (2 wds.) |
| 36% | PAULGAUGUIN | 11 | "Two Tahitian Women" painter who was born in Paris on June 7, 1848: 2 wds. |
| 36% | STAPLETON | 9 | 2016 Best Country Album Grammy winner |
| 35% | RICKYWILLIAMS | 13 | 1998 Heisman Trophy winner who was the runner-up on "Celebrity Big Brother 2" (2 wds.) |
| 35% | STAPLETON | 9 | Grammy winner Chris whose album "From a Room: Volume 2" was released on December 1 |
| 35% | HARRYPOTTER | 11 | Famed wizard at Hogwarts who was born on July 31st... and a hint to solve 27a, 31a, 45a, and 44d: 2 wds. |
| 33% | YITZHAKRABIN | 12 | Former Prime Minister of Israel and Nobel Peace Prize winner who was born in 1922 (2 wds.) |
| 33% | KELLYCLARKSON | 13 | "American Idol" winner who was a coach on "The Voice" for nine seasons (2 wds.) |
| 33% | FIREFLYLANE | 11 | Netflix series about two women who are longtime best friends, based on the Kristin Hannah novel: 2 wds. |
| 33% | BRADLEYCOOPER | 13 | "A Star Is Born" actor who guest-starred as himself on season 3 of "Abbott Elementary": 2 wds. |
| 33% | AMYWINEHOUSE | 12 | "Rehab" singer who was one of Tony Bennett's duet partners on his "Duets II" album: 2 wds. |
| 33% | JENNIFERLOPEZ | 13 | Singer who was nominated for a Grammy for Best Dance Recording in 2000 but lost to Cher: 2 wds. |
| 33% | PATRICKREED | 11 | American pro golfer who is best known for being the winner of the 2014 WGC-Cadillac Championship: 2 wds. |
| 33% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 33% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 33% | NATHANMORRIS | 12 | Founding member of Boyz II Men who was born on June 18, 1971 (2 wds.) |
| 32% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |