| 100% | TBONE | 5 | Burnett who's won Grammys for three different movie soundtracks: 2 wds. |
| 52% | TBONE | 5 | Burnett who won four Grammys for the "O Brother, Where Art Thou?" soundtrack: 2 wds. |
| 37% | SUREBET | 7 | Racehorse who's guaranteed to win, for example: 2 wds. |
| 36% | THEBOX | 6 | 2020 Roddy Ricch chart-topper nominated for three Grammys: 2 wds. |
| 35% | KLAYTHOMPSON | 12 | Warriors shooting guard who's won three NBA championships, and whose dad Mychal also has two NBA titles: 2 wds. |
| 34% | JAMESLBROOKS | 12 | Filmmaker who won three Oscars (Best Picture, Director, and Adapted Screenplay) for 1983's "Terms of Endearment": 3 wds. |
| 34% | ONO | 3 | Yoko who's won three Grammys |
| 33% | STEVIEWONDER | 12 | "Superstition" singer who has won 25 Grammys: 2 wds. |
| 32% | TIGERWOODS | 10 | Golfer who won three U.S. Opens (2 wds.) |
| 32% | NKJEMISIN | 9 | African-American sci-fi novelist who won three consecutive Hugo Awards for Best Novel (3 wds.) |
| 32% | ANGELOU | 7 | Poet who won three Grammys for Best Spoken Word Album |
| 31% | JOHNSALLEY | 10 | First NBA player to win a championship in three different decades and who is also a vegan activist: 2 wds. |
| 31% | GENOAURIEMMA | 12 | Winning coach for all ten of UConn's victories: 2 wds. |
| 31% | LILWAYNE | 8 | "Lollipop" rapper who's won five Grammy Awards: 2 wds. |
| 31% | BILLWALSH | 9 | American football coach who won three Super Bowls for San Francisco 49ers: 2 wds. |
| 31% | JUSTINBIEBER | 12 | "Sorry" singer who's won 23 Teen Choice Awards: 2 wds. |
| 30% | TWOHEARTS | 9 | 1988 Phil Collins hit from the "Buster" movie soundtrack: 2 wds. |
| 30% | ROBERTDOWNEYJR | 14 | Former "SNL" regular who was Oscar-nominated for three movies, including 2023's "Oppenheimer": 3 wds., abbr. |
| 30% | JULIAGARNER | 11 | "Inventing Anna" actress who won three Emmy Awards for playing Ruth Langmore on "Ozark" (2 wds.) |
| 30% | QUINCYJONES | 11 | "Thriller" producer who won the 1982, 1984, and 1991 Grammys for Producer of the Year, Non-Classical: 2 wds. |
| 29% | PHILMICKELSON | 13 | Golfer who won three Masters Tournaments (2 wds.) |
| 29% | ALLISONJANNEY | 13 | Actress who won Emmys for her roles on "Mom," "Masters of Sex," and "The West Wing": 2 wds. |
| 29% | JUDITHLIGHT | 11 | "Who's the Boss?" actress who won a Tony Award for "Other Desert Cities": 2 wds. |
| 29% | CELIA | 5 | Cruz who won three Grammys |
| 29% | RAWLS | 5 | Lou who won three Grammys |
| 29% | KRISJENKINS | 11 | Player who threw the winning, buzzer-beating three-pointer for 22-Across: 2 wds. |
| 29% | JOHNWILLIAMS | 12 | "Jaws" and "Star Wars" composer who has won 26 Grammys: 2 wds. |
| 29% | TOMBRADY | 8 | New England quarterback who's won a record six Super Bowls: 2 wds. |
| 29% | JOANCRAWFORD | 12 | Actress who won an Oscar for 1945's "Mildred Pierce": 2 wds. |
| 29% | SALMANRUSHDIE | 13 | Author who won the Booker Prize for "Midnight's Children": 2 wds. |