| 100% | RACHELMCADAMS | 13 | Winner (with Ryan Gosling) of MTV's 2005 Best Kiss Award for "The Notebook": 2 wds. |
| 63% | BRADLEYCOOPER | 13 | Winner (with Jennifer Lawrence) of MTV's 2013 Best Kiss Award for "Silver Linings Playbook": 2 wds. |
| 58% | CARMENELECTRA | 13 | Winner (with Owen Wilson and Amy Smart) of MTV's 2004 Best Kiss Award for "Starsky & Hutch": 2 wds. |
| 45% | RAINMAN | 7 | Winner of the Academy Award for Best Picture of 1988: 2 wds. |
| 44% | SPINNINGSILVER | 14 | 2019 Locus Award for Best Fantasy Novel winner by 27-Across that's loosely based on the tale of "Rumpelstiltskin" (2 wds.) |
| 39% | BENKINGSLEY | 11 | Winner of a Best Actor Oscar for playing Gandhi, the title role of 1982's Best Picture: 2 wds. |
| 38% | DIANEKEATON | 11 | Winner of a Best Actress Oscar for playing Annie Hall, the title role of 1977's Best Picture: 2 wds. |
| 38% | CHARLTONHESTON | 14 | Winner of a Best Actor Oscar for playing Judah Ben-Hur, the title role of 1959's Best Picture: 2 wds. |
| 37% | CHRISCOLFER | 11 | Winner of the most recent People's Choice Award for Favorite Comedic TV Actor (for "Glee"): 2 wds. |
| 36% | NATHANFILLION | 13 | Winner of the most recent People's Choice Award for Favorite Crime Drama TV Actor (for "Castle"): 2 wds. |
| 36% | ELLENPOMPEO | 11 | Winner of the most recent People's Choice Award for Favorite Dramatic TV Actress (for "Grey's Anatomy"): 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% | THEINCREDIBLES | 14 | Pixar film about a family of superheroes that won the 2005 Annie Award for Best Animated Feature: 2 wds. |
| 35% | VIOLADAVIS | 10 | Winner of the 2015 Primetime Emmy Award for Outstanding Lead Actress in a Drama Series: 2 wds. |
| 35% | DANGELORUSSEL | 13 | No. 1 guard for the LA Lakers, and Jerry West award winner in 2015 : 2 wds. |
| 35% | 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. |
| 35% | INGRIDBERGMAN | 13 | Winner of a Best Actress Oscar for "Gaslight" and a Best Supporting Actress Oscar for "Murder on the Orient Express": 2 wds. |
| 34% | SUPERBOWLMVP | 12 | Award for the star of the NFL's biggest game: 3 wds., abbr. |
| 34% | HEATH | 5 | Ledger who won MTV's 2006 Best Kiss Award (with Jake Gyllenhaal) for "Brokeback Mountain" |
| 34% | THELONDON | 9 | Young Thug song featuring J. Cole and Travis Scott that was nominated for the 2019 MTV Video Music Award for Song of Summer (2 wds.) |
| 34% | CAMILACABELLO | 13 | "Señorita" singer who shared the 2019 MTV Video Music Award for Best Collaboration with 18-Across (2 wds.) |
| 34% | SHAWNMENDES | 11 | "Señorita" singer who shared the 2019 MTV Video Music Award for Best Collaboration with 32-Across (2 wds.) |
| 34% | 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.) |
| 34% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 33% | ALLY | 4 | Sheedy who shared MTV's Silver Bucket of Excellence Award in 2005 for "The Breakfast Club" |
| 33% | TIL | 3 | ___ Tuesday (1985 winners of the MTV Video Music Award for Best New Artist) |
| 33% | EDDIEREDMAYNE | 13 | Best Actor winner for 2014's "The Theory of Everything": 2 wds. |
| 33% | CORMACMCCARTHY | 14 | Author of the 2005 novel "No Country for Old Men," which was made into a Best Picture-winning movie: 2 wds. |
| 33% | 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.) |