| 100% | JOHNLEGEND | 10 | Artist on "Songland" whose "Glory," with Common, won an Oscar for Best Song in 2015: 2 wds. |
| 50% | LADYGAGA | 8 | Singer/actress whose "Shallow" won an Oscar for Best Original Song: 2 wds. |
| 45% | LUDOVICBOURCE | 13 | French composer who won an Oscar for Best Original Score for 2011's "The Artist" (2 wds.) |
| 45% | LETITGO | 7 | "Frozen" song that won an Oscar for Best Original Song in 2014 (3 wds.) |
| 44% | NICOLEKIDMAN | 12 | Actress who won an Oscar for Best Actress for "The Hours" and a Worst Screen Couple Razzie Award with Will Ferrell for "Bewitched": 2 wds. |
| 44% | ENNIOMORRICONE | 14 | Italian composer who won an Oscar for Best Original Score for 2015's "The Hateful Eight" (2 wds.) |
| 43% | KEVINCOSTNER | 12 | Actor who plays Frank Farmer in 18a and has also won an Oscar for Best Director for "Dances with Wolves": 2 wds. |
| 43% | CITYOFSTARS | 11 | "La La Land" song that won an Oscar for Best Original Song in 2017 (3 wds.) |
| 41% | ISAACHAYES | 10 | "Soul Man" singer who won an Academy Award for Best Original Song for his work on the film "Shaft": 2 wds. |
| 41% | EDMUNDGWENN | 11 | "Mister 880" actor who won an Oscar for playing Kris Kringle in the 1947 Christmas classic "Miracle on 34th Street" (2 wds.) |
| 41% | CLINTEASTWOOD | 13 | Actor and filmmaker who won an Oscar for Best Director at 74 for "Million Dollar Baby": 2 wds. |
| 41% | SAMSMITH | 8 | Singer-songwriter whose song "Writing's on the Wall" from the movie "Spectre" won him an Oscar in 2015: 2 wds. |
| 41% | FIGHTFORYOU | 11 | "Judas and the Black Messiah" song that won an Oscar for Best Original Song in 2021 (3 wds.) |
| 41% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 41% | SAMSMITH | 8 | Nonbinary singer who won an Oscar for the Bond theme "Writing's on the Wall": 2 wds. |
| 40% | JENNIFERHUDSON | 14 | Actress who won an Oscar for her first feature film role, in "Dreamgirls": 2 wds. |
| 40% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title role in 39-Across: 2 wds. |
| 40% | JAMIEFOXX | 9 | Actor who won an Oscar for portraying Ray Charles in a 2004 biopic: 2 wds. |
| 40% | NICOLEKIDMAN | 12 | "Moulin Rouge!" and "The Hours" star who was the first Australian to win an Oscar for Best Actress and the first to be nominated in consecutive years (2 wds.) |
| 40% | MARLONBRANDO | 12 | "On the Waterfront" actor who won an Oscar for portraying 40-Across in 1972's "The Godfather": 2 wds. |
| 40% | JULIEANDREWS | 12 | Actress who won an Oscar for her first feature film role, in "Mary Poppins": 2 wds. |
| 40% | MACKLEMORE | 10 | Artist on NBC's "Songland" whose "The Heist," with Ryan Lewis, won a 2014 Grammy for best rap album |
| 40% | RAMIMALEK | 9 | Actor who became the first one of Egyptian heritage to win an Oscar for Best Actor in 2019: 2 wds. |
| 40% | LIZAMINNELLI | 12 | Actress who won an Oscar for Best Actress for "Cabaret" and a Worst Actress Razzie Award for "Rent-a-Cop": 2 wds. |
| 40% | LUPITANYONGO | 12 | Actress who won an Oscar for her first feature film role, in "12 Years a Slave": 2 wds. |
| 39% | TRAININGDAY | 11 | 2001 thriller directed by Antoine Fuqua that won an Oscar for Best Actor (2 wds.) |
| 39% | SANDRABULLOCK | 13 | Actress who won an Oscar for Best Actress for "The Blind Side" and a Worst Actress Razzie Award for "All About Steve": 2 wds. |
| 39% | WHITECHRISTMAS | 14 | Irivng Berlin song sung by 53-Across in 16-Across that won an Oscar for Best Original Song (2 wds.) |
| 39% | WHATWASI | 8 | With 48-Across, Billie Eilish hit from "Barbie" that won an Oscar for Best Original Song: 3 wds. |
| 39% | GOSFORDPARK | 11 | 2001 drama directed by Robert Altman that won an Oscar for Best Original Screenplay (2 wds.) |