| 100% | TBONE | 5 | Burnett who won four Grammys for the "O Brother, Where Art Thou?" soundtrack: 2 wds. |
| 45% | TBONE | 5 | Burnett who's won Grammys for three different movie soundtracks: 2 wds. |
| 42% | HOLLYHUNTER | 11 | "The Piano" actress who played Penny in "O Brother, Where Art Thou?": 2 wds. |
| 42% | JOHNGOODMAN | 11 | "The Conners" actor who played Big Dan in "O Brother, Where Art Thou?": 2 wds. |
| 41% | KACEYMUSGRAVES | 14 | 19-Across and 46-Across singer who won four 2019 Grammys, including Album of the Year and Best Country Album for "Golden Hour" (2 wds.) |
| 39% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 39% | NICKIMINAJ | 10 | "Anaconda" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist four times: 2 wds. |
| 39% | QUINCYJONES | 11 | "Thriller" producer who won the 1982, 1984, and 1991 Grammys for Producer of the Year, Non-Classical: 2 wds. |
| 38% | GEORGECLOONEY | 13 | "Ocean's Eleven" actor who played Everett in "O Brother, Where Art Thou?": 2 wds. |
| 38% | STEPHENKING | 11 | "Carrie" author who won a 1996 O. Henry Award for his short story "The Man in the Black Suit": 2 wds. |
| 37% | DAVIDFOSTER | 11 | "Let's Talk About Love" producer who won the 1985, 1992, and 1994 Grammys for Producer of the Year, Non-Classical: 2 wds. |
| 35% | MISSYFRANKLIN | 13 | 17-year-old American swimmer who won four gold medals at the 2012 Olympics: 2 wds. |
| 35% | LIZAMINNELLI | 12 | "Arthur" actress who won the Best Actress Oscar for "Cabaret": 2 wds. |
| 35% | SALMANRUSHDIE | 13 | Author who won the Booker Prize for "Midnight's Children": 2 wds. |
| 35% | CHARLESYU | 9 | Author who won the 2020 National Book Award for Fiction for "Interior Chinatown": 2 wds. |
| 35% | SUSANCHOI | 9 | Author who won the 2019 National Book Award for Fiction for "Trust Exercise": 2 wds. |
| 35% | GREGGPOPOVICH | 13 | NBA coach for the Spurs who won the championship five times, including 2014: 2 wds. |
| 35% | MARGARETATWOOD | 14 | Author who won the Booker Prize for "The Blind Assassin" and "The Testaments": 2 wds. |
| 35% | NICOLEKIDMAN | 12 | Australian actress who won the Best Actress Oscar for 2002's "The Hours": 2 wds. |
| 35% | AMA | 3 | "I ___ Man of Constant Sorrow" (song in "O Brother, Where Art Thou?"): 2 wds. |
| 35% | SALMANRUSHDIE | 13 | Author who won the Man Booker Prize in 1981 for "Midnight's Children": 2 wds. |
| 35% | LORNEMICHAELS | 13 | "SNL" producer who won the Mark Twain Prize for American Humor in 2004: 2 wds. |
| 35% | ALISONKRAUSS | 12 | Singer who won her 27th Grammy for the 2011 bluegrass album "Paper Airplane": 2 wds. |
| 35% | JOELGREY | 8 | "Wicked" actor who won the Best Supporting Actor Oscar for 1972's "Cabaret": 2 wds. |
| 35% | CATEBLANCHETT | 13 | Australian actress who won the Best Actress Oscar for 2013's "Blue Jasmine": 2 wds. |
| 35% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 35% | MARTINBRODEUR | 13 | New Jersey Devils goalie who won the Vezina Trophy four times: 2 wds. |
| 35% | TYRONNLUE | 9 | NBA coach for the Cavaliers who won the championship in 2016: 2 wds. |
| 35% | ELEANORCATTON | 13 | Canadian author who won the Man Booker Prize for "The Luminaries": 2 wds. |
| 34% | ALLISONJANNEY | 13 | "Mom" star who won four Emmy Awards for playing C.J. Cregg on "The West Wing" (2 wds.) |