| 100% | PREMEEMOHAMED | 13 | Writer whose "And What Can We Offer You Tonight" won the Nebula Award for Best Novella in 2022 (2 wds.) |
| 53% | PDJELICLARK | 11 | Writer whose "A Master of Djinn" won the Nebula Award for Best Novel in 2022 (3 wds.) |
| 40% | WIZKHALIFA | 10 | "See You Again" rapper who won the BET Award for Best New Artist in 2011: 2 wds. |
| 39% | GABRIELLEZEVIN | 14 | 16-Across and 28-Across writer whose novel "Tomorrow, and Tomorrow, and Tomorrow" won the Goodreads Choice Award Winner for Best Fiction in 2022 (2 wds.) |
| 39% | TESSGUNTY | 9 | Writer whose novel "The Rabbit Hutch" won the 2022 National Book Award for Fiction (2 wds.) |
| 38% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 37% | MARYMARTIN | 10 | She won three Tony Awards for Best Actress in a Musical, for "South Pacific," "Peter Pan," and "The Sound of Music": 2 wds. |
| 37% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 36% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 36% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 36% | RODDYRICCH | 10 | "The Box" rapper who won the BET Award for Best New Artist in 2020: 2 wds. |
| 36% | LINDSEYVONN | 11 | Alpine skier who won the Best Female Athlete ESPY Award in 2010 and 2011: 2 wds. |
| 36% | SERENAWILLIAMS | 14 | Tennis player who won the Best Female Athlete ESPY Award in 2003 and 2013: 2 wds. |
| 36% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 36% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 36% | JORDANPEELE | 11 | He won the Bram Stoker Award for Best Screenplay twice, for "Get Out" and "Us": 2 wds. |
| 36% | RONDAROUSEY | 11 | Mixed martial artist who won the Best Female Athlete ESPY Award in 2014 and 2015: 2 wds. |
| 36% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 35% | REGINAKING | 10 | She won the 2019 Oscar for Best Supporting Actress for her role in "If Beale Street Could Talk": 2 wds. |
| 35% | BRYANCRANSTON | 13 | "Breaking Bad" actor who won two Tony Awards for Best Actor in a Play, for "All the Way" and "Network" (2 wds.) |
| 35% | GWENVERDON | 10 | She won three Tony Awards for Best Actress in a Musical, for "Damn Yankees," "New Girl in Town," and "Redhead": 2 wds. |
| 35% | RENEEZELLWEGER | 14 | Actress who won the Academy Award for Best Actress in 2020 for playing the title role in "Judy" (2 wds.) |
| 35% | JOAQUINPHOENIX | 14 | Actor who won the Academy Award for Best Actor in 2020 for playing the title role in "Joker" (2 wds.) |
| 35% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 35% | MARTINESPADA | 12 | Writer whose collection "Floaters" won the 2021 National Book Award for Poetry (2 wds.) |
| 35% | JONATHANGROFF | 13 | "Frozen" voice actor who won the 2024 Best Leading Actor in a Musical Tony for "Merrily We Roll Along": 2 wds. |
| 35% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 35% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 34% | CHARLESYU | 9 | Writer whose novel "Interior Chinatown" won the 2020 National Book Award for Fiction (2 wds.) |
| 34% | SUSANCHOI | 9 | Writer whose novel "Trust Exercise" won the 2019 National Book Award for Fiction (2 wds.) |