| 100% | PIMP | 4 | "It's Hard out Here for a ___" (Oscar-winning hip-hop song) |
| 66% | PIMP | 4 | "It's Hard Out Here for a ___" (song from the "Hustle & Flow" soundtrack) |
| 48% | FRANKCAPRA | 10 | "It's a Wonderful Life" director who has won 3 Oscars out of 6 nominations for Best Director: 2 wds. |
| 42% | HIT | 3 | ___-Boy, hip hop music producer who won a Grammy for "Racks in the Middle" |
| 42% | HER | 3 | She won a 2021 Oscar for the song "Fight for You" |
| 41% | INERTGAS | 8 | It's hard to get a reaction out of it |
| 41% | REDCARPET | 9 | It's rolled out for a celebrity |
| 41% | LOWERLIP | 8 | It's out for a pout |
| 40% | CARDI | 5 | ___ B, hip hop star who became the first female rapper to win a Grammy for Best Rap Album |
| 40% | TARP | 4 | It's rolled out for a rain delay |
| 40% | HER | 3 | R&B artist who won a Best Original Song Oscar for "Fight for You" |
| 40% | HOLIDAYINN | 10 | 1942 film that won a Best Original Song Oscar for 34-Across: 2 wds. |
| 40% | JINGLE | 6 | __ bells, it's a festive song for winter |
| 40% | CAHN | 4 | Sammy —, lyricist who won a Best Original Song Oscar for Three Coins in a Fountain |
| 39% | STARTED | 7 | "Let's Get It ___," 2004 song by the Black Eyed Peas that won a Grammy for Best Rap Performance by a Duo or Group |
| 39% | LINE | 4 | It's drawn for a tic-tac-toe win |
| 38% | SKYFALL | 7 | Adele title song from a James Bond movie that won the Oscar for Best Original Song in 2013 |
| 37% | ONEMILLION | 10 | "__ B.C.," a 1940 fantasy film which won the Oscar for Best Special Effects for its depiction of dinosaurs: 2 wds. |
| 36% | BLANCHETT | 9 | "The House with a Clock in Its Walls" actress Cate who also won an Oscar for her role in "Blue Jasmine" |
| 36% | CARRADINE | 9 | Keith —, actor who won a Best Music, Original Song Oscar for I'm Easy from 1975's Nashville |
| 36% | BILLIEEILISH | 12 | Songwriter who won her second Oscar, for a song from 2023's "Barbie," at age 22: 2 wds. |
| 36% | MLEM | 4 | Internet slang for a cat sticking its tongue out |
| 35% | JANET | 5 | ___ Jackson, Hip Hop artist whose song "What's It Gonna Be?!" had one of the most expensive music videos |
| 35% | ENYA | 4 | Oscar nominee for the song "May It Be" |
| 35% | ENYA | 4 | Oscar nominee for the song “May It Be” |
| 35% | ANDERSONPAAK | 12 | LA hip-hop artist who won a 2019 Grammy for Best Rap Performance for "Bubblin": 2 wds. |
| 35% | OSOLEMIO | 8 | Song for which 17-Across won a Grammy |
| 35% | CALLIEKHOURI | 12 | Screenwriter who won a Best Original Screenplay Oscar for 1991's "Thelma & Louise": 2 wds. |
| 35% | EMERALDFENNELL | 14 | Screenwriter who won a Best Original Screenplay Oscar for 2020's "Promising Young Woman": 2 wds. |
| 35% | SOFIACOPPOLA | 12 | Screenwriter who won a Best Original Screenplay Oscar for 2003's "Lost in Translation": 2 wds. |