| 100% | CARMENELECTRA | 13 | Winner (with Owen Wilson and Amy Smart) of MTV's 2004 Best Kiss Award for "Starsky & Hutch": 2 wds. |
| 52% | RACHELMCADAMS | 13 | Winner (with Ryan Gosling) of MTV's 2005 Best Kiss Award for "The Notebook": 2 wds. |
| 51% | BRADLEYCOOPER | 13 | Winner (with Jennifer Lawrence) of MTV's 2013 Best Kiss Award for "Silver Linings Playbook": 2 wds. |
| 33% | RAINMAN | 7 | Winner of the Academy Award for Best Picture of 1988: 2 wds. |
| 32% | SPINNINGSILVER | 14 | 2019 Locus Award for Best Fantasy Novel winner by 27-Across that's loosely based on the tale of "Rumpelstiltskin" (2 wds.) |
| 32% | 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. |
| 31% | BRIANKVAUGHAN | 13 | 2013 and 2024 Hugo Award winner for Best Graphic Story or Comic for two volumes of his "Saga" series: 3 wds. |
| 30% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 30% | GENEHACKMAN | 11 | Winner of a Best Actor Oscar for "The French Connection" and a Best Supporting Actor Oscar for "Unforgiven": 2 wds. |
| 29% | INGRIDBERGMAN | 13 | Winner of a Best Actress Oscar for "Gaslight" and a Best Supporting Actress Oscar for "Murder on the Orient Express": 2 wds. |
| 29% | HEATH | 5 | Ledger who won MTV's 2006 Best Kiss Award (with Jake Gyllenhaal) for "Brokeback Mountain" |
| 29% | JORDANPEELE | 11 | He won the Bram Stoker Award for Best Screenplay twice, for "Get Out" and "Us": 2 wds. |
| 29% | REHAB | 5 | 2008 Grammy Award for Song of the Year and Record of the Year winner by Amy Winehouse |
| 29% | MICHAELKEATON | 13 | Actor who shared SAG Awards for Outstanding Performance by an Ensemble in a Motion Picture with the casts of 18-Across and 33-Across (2 wds.) |
| 28% | ASTRANGELOOP | 12 | Winner of Best Musical at the 75th Tony Awards, and the 2020 Pulitzer Prize for Drama |
| 28% | BENKINGSLEY | 11 | Winner of a Best Actor Oscar for playing Gandhi, the title role of 1982's Best Picture: 2 wds. |
| 28% | SACHA | 5 | Baron Cohen who won MTV's 2007 Best Kiss Award (with Will Ferrell) for "Talladega Nights" |
| 28% | AVENUEQ | 7 | Winner of the 2004 Tony Award for Best Musical |
| 28% | MARIKOTAMAKI | 12 | Writer/artist who won the 2020 Eisner Award for Best Writer for the comics series "Harley Quinn: Breaking Glass," "Laura Dean Keeps Breaking Up with Me," and "Archie" (2 wds.) |
| 27% | PHANTOMLADY | 11 | 2021 Edgar Award for Best Critical/Biographical winner by Christina Lane (2 wds.) |
| 27% | GWENVERDON | 10 | She won three Tony Awards for Best Actress in a Musical, for "Damn Yankees," "New Girl in Town," and "Redhead": 2 wds. |
| 27% | DIANEKEATON | 11 | Winner of a Best Actress Oscar for playing Annie Hall, the title role of 1977's Best Picture: 2 wds. |
| 27% | CHAINOFFOOLS | 12 | Aretha Franklin's 1967 single that won her a Grammy for Best Female R&B Vocal Performance and later a Grammy Hall Of Fame Award: 3 wds. |
| 27% | THECOMPANION | 12 | 2021 Edgar Award for Best Young Adult Fiction winner by Katie Alender (2 wds.) |
| 27% | ANGELALANSBURY | 14 | She won a record four Tony Awards for Best Actress in a Musical, for "Mame," "Dear World," "Gypsy," and "Sweeney Todd": 2 wds. |
| 27% | CHARLTONHESTON | 14 | Winner of a Best Actor Oscar for playing Judah Ben-Hur, the title role of 1959's Best Picture: 2 wds. |
| 27% | SORRYNOTSORRY | 13 | Top 10 43-Across song nominated for the 2017 MTV "Song of Summer" Video Music Award and the 2018 MTV "Best Pop Video" Video Music Award (3 wds.) |
| 27% | BENKINGSLEY | 11 | Actor born in England who won the Academy Award for Best Actor for his portrayal of Mahatma Gandhi in the movie "Gandhi": 2 wds. |
| 27% | ALANALDA | 8 | Actor with Emmy awards for "The West Wing" and "M*A*S*H" (2 wds.) |