| 100% | TONYBENNETT | 11 | 2018 AP Coach of the Year who shares his name with the singer of "I Left My Heart in San Francisco": 2 wds. |
| 47% | TONYBENNETT | 11 | "I Left My Heart in San Francisco" singer honored with the 2017 Gershwin Prize for Popular Song (2 wds.) |
| 46% | TONYBENNETT | 11 | "I Left My Heart in San Francisco" singer who's an accomplished painter: 2 wds. |
| 41% | MARS | 4 | Bruno ___, "Leave the Door Open" singer who shares his name with the god of war in Roman mythology |
| 40% | FREDDIEMERCURY | 14 | Queen lead singer who shares his name with the smallest planet in the solar system (2 wds.) |
| 39% | 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. |
| 37% | MICHAELSTIPE | 12 | Singer who came up with "It's the End of the World as We Know It (And I Feel Fine)" in his sleep: 2 wds. |
| 37% | BRUNOMARS | 9 | "Uptown Funk" singer who shares his name with the fourth planet from the sun (2 wds.) |
| 36% | JOHNLEGEND | 10 | "All of Me" singer and "The Voice" coach who was named People's Sexiest Man Alive in 2019: 2 wds. |
| 36% | ERICCLAPTON | 11 | "Layla" guitarist who shares his first name with the prince in "The Little Mermaid": 2 wds. |
| 35% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 35% | JENNIFERLOPEZ | 13 | "Let's Get Loud" singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| 35% | TONYBENNETT | 11 | "I Left My Heart in San Francisco" singer (1926-2023) |
| 35% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 34% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 34% | CONWAYTWITTY | 12 | Country Music Hall of Fame singer who shared four consecutive CMA Awards for Vocal Duo of the Year with 28-Across in the 1970s (2 wds.) |
| 34% | TONY | 4 | Singer Bennett whose signature song was "I Left My Heart in San Francisco" |
| 34% | CAITLINCLARK | 12 | Iowa Hawkeyes championship game scoring leader who was named AP Player of the Year and Naismith College Player of the Year in 2023 (2 wds.) |
| 34% | DAWNSTALEY | 10 | University of South Carolina women's basketball coach who was named Naismith Coach of the Year in 2020, 2022, and 2023 (2 wds.) |
| 34% | TARAVANDERVEER | 14 | Stanford University women's basketball coach who was named Naismith Coach of the Year in 1990, 2011, and 2021 (2 wds.) |
| 33% | DANHURLEY | 9 | Head coach of 13-Across who was named Naismith Coach of the Year in 2024 (2 wds.) |
| 33% | BLANCO | 6 | "The Git Up" singer Brown who shares his name with a type of vino |
| 33% | TIMBERLAKE | 10 | Justin ___, a singer famous for his hit single "Cry Me a River", who starred in the film "Friends with Benefits": 2 wds. |
| 33% | BENNETT | 7 | Tony __ sang I Left My Heart in San Francisco |
| 33% | ARIANAGRANDE | 12 | 17-Across and 39-Across singer who was named Billboard's 2018 Woman of the Year (2 wds.) |
| 33% | GEORGESTRAIT | 12 | "I Cross My Heart" country singer named the ACM Artist of the Decade for the 2000s: 2 wds. |
| 33% | ILEFT | 5 | "___ My Heart in San Francisco": 2 wds. |
| 33% | STEFFIGRAF | 10 | Tennis player who won the AP Athlete of the Year award in 1989: 2 wds. |
| 33% | RICHARDWRIGHT | 13 | Pink Floyd keyboardist who shares a name with the author of "Native Son" (2 wds.) |
| 33% | PATSUMMITT | 10 | University of Tennessee women's basketball coach who was named Naismith Coach of the Year in 1987, 1989, 1994, 1998, and 2004 (2 wds.) |