| 100% | ONAROLL | 7 | Winning, winning, and winning some more (3 wds.) |
| 64% | RUNTHISTOWN | 11 | 2009 single from Jay-Z, featuring Rihanna and Kanye West, that won the trio many awards, including two Grammys and an Emmy : 3 wds. |
| 58% | TONYLARUSSA | 11 | Athletics/Cardinals manager who won six pennants and three World Series: 3 wds. |
| 58% | LETITGO | 7 | Song from "Frozen", which won a Grammy and an Academy Award: 3 wds. |
| 58% | ALLABOUTSTEVE | 13 | 2009 film that won Razzies for Worst Actress and Worst Screen Couple: 3 wds. |
| 57% | CYYOUNGAWARD | 12 | Pitching prize won by 30-Across in 1997, 1999, and 2000: 3 wds. |
| 55% | JAMESEARLJONES | 14 | Actor who voiced Darth Vader and won two Tony Awards for Best Actor: 3 wds. |
| 54% | NKJEMISIN | 9 | Sci-fi author whose 2017 novel "The Stone Sky" won both the Hugo and Nebula Awards: 3 wds. |
| 53% | MICHAELJFOX | 11 | Actor who won Emmys for his roles on "Rescue Me," "Spin City," and "Family Ties": 3 wds. |
| 52% | ORSONSCOTTCARD | 14 | "Ender's Game" author who won a Hugo and a Nebula in the same year, twice: 3 wds. |
| 52% | ARTHURCCLARKE | 13 | "Rendezvous With Rama" author who won a Hugo and a Nebula in the same year, twice: 3 wds. |
| 52% | MARYTYLERMOORE | 14 | Laura Petrie portrayer who won Emmys in 1964 and 1966 for "The Dick Van Dyke Show": 3 wds. |
| 52% | WAITFORU | 8 | #1 hit by Future featuring Drake and Tems that won the 2023 BET Best Collaboration Award: 3 wds. |
| 52% | YAKYAK | 6 | Gab and gab some more |
| 52% | SLEEPSIN | 8 | Lies and lies some more? |
| 52% | THESHAPEOF | 10 | With 55-Across, 2017 Guillermo del Toro sci-fi/fantasy film that won Best Picture and three other Oscars: 3 wds. |
| 52% | JAMESLBROOKS | 12 | Filmmaker who won three Oscars (Best Picture, Director, and Adapted Screenplay) for 1983's "Terms of Endearment": 3 wds. |
| 52% | JUANMARICHAL | 12 | Dominican pitcher who won 243 games (third most for a Latin American pitcher) between 1960 and 1974: 2 wds. |
| 52% | PEDROMARTINEZ | 13 | Dominican pitcher who won 219 games (fifth most by a Latin American pitcher) between 1993 and 2009: 2 wds. |
| 51% | ONATEAR | 7 | Winning game after game: 3 wds. |
| 51% | YAK | 3 | Talk, talk, and talk some more |
| 51% | YAK | 3 | Talk, talk ... and talk some more |
| 51% | CASSIDYANDTHE | 13 | "Butch ___ Sundance Kid," 1969 Western film based on the outlaws Robert LeRoy Parker and Harry Longabaugh that won four Oscars: 3 wds. |
| 51% | KISSMEKATE | 10 | 1948 Broadway show, with music and lyrics by 41-Across, that won the first Tony for Best Musical: 3 wds. |
| 51% | ROBERTDENIRO | 12 | He won a Best Actor Oscar for "Raging Bull" and Best Supporting Actor for "The Godfather Part II": 3 wds. |
| 51% | THEKINGSSPEECH | 14 | 2010 historical drama about George VI that won both the Best Picture Oscar and the Best Film BAFTA: 3 wds. |
| 51% | CHARIOTSOFFIRE | 14 | 1981 historical drama about Olympic runners that won both the Best Picture Oscar and the Best Film BAFTA: 3 wds. |
| 51% | SHOHEIOHTANI | 12 | Los Angeles Angels pitcher, outfielder, and designated hitter who won the 2021 American League Most Valuable Player Award (2 wds.) |
| 50% | ATEUPASTORM | 11 | Gorged, gorged and gorged some more, informally |
| 50% | STEVENASH | 9 | Suns guard who won the NBA Most Valuable Player award in 2005 and 2006: 2 wds. |