| 100% | VITOCORLEONE | 12 | Academy Award-winning role for both 20- and 26-Across |
| 50% | LOUGRANT | 8 | Role for which Ed Asner won both comedy and drama Emmys |
| 48% | JOKER | 5 | Oscar-winning role for both Heath Ledger and Joaquin Phoenix |
| 46% | EMMY | 4 | Award won for 39- and 41-Across's programs |
| 44% | 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. |
| 44% | MILLS | 5 | Hayley ___, British actress who won the Academy Juvenile Award for her role in "Pollyanna" |
| 44% | FOUR | 4 | Number of Emmy Awards for acting won by both Bryan Cranston and Dennis Franz |
| 44% | EMILYHENRY | 10 | 18-Across, 26-Across, and 35-Across novelist who won the 2021, 2022, and 2023 Goodreads Choice Award for Best Romance (2 wds.) |
| 43% | NELL | 4 | Carter who won both a Tony and an Emmy for her role in Ain't Misbehavin' |
| 43% | ARCHIEMANNING | 13 | College Football Hall of Famer whose sons Peyton and Eli both won the NFL Man of the Year award named for 18-Across (2 wds.) |
| 43% | BEBE | 4 | ___ Neuwirth, actress who played Lilith Sternin on "Cheers" and won two Emmy Awards for her role |
| 43% | RHEA | 4 | ___ Perlman, actress who played Carla Tortelli on "Cheers" and won four Emmy Awards for her role |
| 43% | TED | 3 | ___ Danson, actor who played Sam Malone on "Cheers" and won two Emmy Awards for his role |
| 43% | CLINTBLACK | 10 | 18-Across, 26-Across, and 35-Across country singer who won four 1989 Academy of Country Music Awards, including Top Male Vocalist (2 wds.) |
| 43% | KINTE | 5 | Role for both Burton and Amos in a 1977 miniseries |
| 43% | CARLYSIMON | 10 | Artist who won an Academy, Golden Globe and Grammy Award for 1989's "Let the River Run" |
| 42% | ANYTHINGGOES | 12 | 1934 show with music and lyrics by 39-Across whose 1987 and 2011 revivals both won the Tony Award for Best Revival of a Musical (2 wds.) |
| 41% | ALI | 3 | Academy Award winner for "Moonlight" and "Green Book" |
| 41% | NOMADLAND | 9 | 50-Across film that won Academy Awards in 2021 for Best Picture, Best Actress, and Best Director |
| 41% | WESTSIDESTORY | 13 | 24-Across won both a Tony and an Oscar for this |
| 40% | EMMY | 4 | Award won by Kieran Culkin for his role on "Succession" |
| 40% | OSCARS | 6 | Awards won by Mahershala Ali for “Moonlight” and “Green Book” |
| 40% | ANITA | 5 | "West Side Story" role that won Oscars for both Rita Moreno and Ariana DeBose |
| 40% | KILLINTIME | 10 | Album by 45-Across featuring the singles 18-Across and 26-Across that won the 1989 Album of the Year Academy of Country Music Award (2 wds.) |
| 39% | OSCAR | 5 | Award won by Kieran Culkin for his role in "A Real Pain" |
| 39% | EMMY | 4 | Award won by Elaine Stritch for her recurring role on "30 Rock" |
| 39% | MEDEA | 5 | Role for which Judith Anderson, Zoe Caldwell and Diana Rigg won Tonys |
| 39% | ISSA | 4 | Rae who won NAACP Image Awards in 2022 for both acting in and writing "Insecure" |
| 39% | SCHINDLERSLIST | 14 | 1993 film for which 46-Across won a Grammy Award and an Oscar (2 wds.) |
| 39% | MORGANFREE | 10 | Academy Award winner who has played both a U.S. president and God |