| 100% | KEVINSPACEY | 11 | "House of Cards" star who has won two Academy Awards, one of them for "American Beauty": 2 wds |
| 59% | JACKNICHOLSON | 13 | "The Shining" actor who has won two oscars, one of them for "As Good as it Gets": 2 wds |
| 49% | STEVIEWONDER | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Innervisions": 2 wds. |
| 49% | JOHNHANES | 9 | American engineer/mixer who has won the Grammy thrice for "Best Album of the Year," including one for "24k Magic": 2 wds. |
| 48% | FRANKSINATRA | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "September of My Years": 2 wds. |
| 48% | PAULSIMON | 9 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Bridge over Troubled Water": 2 wds. |
| 48% | PRIYANKACHOPRA | 14 | Bollywood star who has won two People's Choice Awards: 2 wds. |
| 44% | ROBINWRIGHT | 11 | "House of Cards" star who was nominated for the 2017 Emmy Award for Outstanding Lead Actress in a Drama Series (2 wds.) |
| 44% | ARCHIEMANNING | 13 | Former American football quarterback who is the father of Peyton and Eli, both of whom have won two Super Bowls: 2 wds. |
| 43% | SIDNEYSHELDON | 13 | American author who wrote "If Tomorrow Comes", and won an Academy Award for "The Bachelor and the Bobby-Soxer": 2 wds. |
| 43% | 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. |
| 43% | DAKOTAJOHNSON | 13 | Actress who won two Razzie Awards for "Fifty Shades of Grey" (2 wds.) |
| 43% | JESSICATANDY | 12 | "Driving Miss Daisy" star who is the oldest winner of the Academy Award for Best Actress (2 wds.) |
| 43% | ASONG | 5 | "Sunrise: ___ of Two Humans," 1927 silent romantic drama that won the first Academy Award for Best Cinematography in 1929: 2 wds. |
| 43% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 43% | SIDNEYPOITIER | 13 | 15-Across, 30-Across, and "Lilies of the Field" star who was the first Black man to win an Academy Award for Best Actor (2 wds.) |
| 42% | MARLEEMATLIN | 12 | "Children of a Lesser God" star who is the youngest winner of the Academy Award for Best Actress (2 wds.) |
| 42% | ARTHURASHKIN | 12 | American scientist who won one half of the 2018 Nobel Prize in Physics for his work on optical tweezers: 2 wds. |
| 42% | ANNEBANCROFT | 12 | "The Miracle Worker" star who won the Oscar for Best Actress at the 35th Academy Awards (2 wds.) |
| 41% | SEANPENN | 8 | Two time Academy Award winning actor of "Mystic River" who appeared in a guest role on "Two and a Half Men": 2 wds. |
| 41% | ANDREAGASSI | 11 | Retired American tennis star who has won eight Grand Slams: 2 wds |
| 41% | ROSELAVELLE | 11 | Midfielder for the USWNT who won the Bronze Ball award and scored one of the two goals in the team's World Cup final game victory over 17-Across (2 wds.) |
| 41% | CLINTEASTWOOD | 13 | "Million Dollar Baby" director who has won 2 Oscars out of 4 nominations for Best Director: 2 wds. |
| 41% | AIMEEMANN | 9 | Grammy award winning female bassist who has been named one of the world's top ten greatest living songwriters by NPR: 2 wds. |
| 41% | HERBIEHANCOCK | 13 | American bandleader and composer who won an Academy Award for Best Original Score for the 1986 movie "Round Midnight" (2 wds.) |
| 40% | BYRONSCOTT | 10 | One of the greatest players of the LA Lakers who won three NBA Championships and went on to coach the team for two years: 2 wds. |
| 40% | MARLEEMATLIN | 12 | Performer who won an Academy Award for Best Actress for playing Sarah Norman in her film debut, "Children of a Lesser God" (2 wds.) |
| 40% | FRANKCAPRA | 10 | "It's a Wonderful Life" director who has won 3 Oscars out of 6 nominations for Best Director: 2 wds. |
| 40% | DAVIDEKELLEY | 12 | Writer/producer who has won 11 Emmy Awards, including one for Outstanding Limited Series for 29-Across (3 wds.) |
| 40% | KEVINDURANT | 11 | 2008 NBA Rookie of the Year (with the SuperSonics) who has won two championship rings: 2 wds. |