| 100% | TWEETY | 6 | "Headliner" of the first Warner Bros. short to win an Oscar |
| 49% | ADELE | 5 | Singer of the first James Bond movie theme song ever to win an Academy Award |
| 47% | CAPRA | 5 | Director of the first film to win all five top Oscars (Best Picture, Director, Actor, Actress and Screenplay) |
| 47% | ALI | 3 | Mahershala who was the first Muslim performer to win an Oscar |
| 47% | ALI | 3 | Mahershala who was the first Muslim actor to win an Oscar |
| 47% | RAMIMALEK | 9 | Actor who became the first one of Egyptian heritage to win an Oscar for Best Actor in 2019: 2 wds. |
| 43% | GODFATHER | 9 | First sequel to win an Oscar for Best Picture |
| 43% | FOSSE | 5 | Only person to win an Oscar, Emmy and Tony in the same year (1973) |
| 43% | EMINEM | 6 | First rapper to win an Oscar for Best Original Song |
| 43% | SHREK | 5 | First film to win an Oscar for Best Animated Feature |
| 43% | ADELE | 5 | Singer who won an Oscar for the theme to "Skyfall" |
| 43% | CURIE | 5 | Surname of the first woman to win a Nobel prize |
| 43% | MORENO | 6 | First Hispanic actress to win an Oscar, Rita __ |
| 43% | MCDANIEL | 8 | First Black actress to win an Oscar, Hattie __ |
| 42% | THECONTINENTAL | 14 | First song to win an Oscar, 1934 (written by Con Conrad) |
| 42% | ADELE | 5 | First songwriter to win an Oscar for a James Bond theme |
| 42% | DEMME | 5 | Director Jonathan who won an Oscar for "The Silence of the Lambs" |
| 42% | SPANISH | 7 | Penelope Cruz, first __ actress to win an Oscar |
| 41% | EVELYNASHFORD | 13 | The first track and field athlete to run 100 meters under 11 seconds in an Olympic Games and who has won a total of 5 Olympic medals: 2 wds. |
| 41% | SIDNEY | 6 | Actor and director Poitier, the first black person to win an Oscar for best actor |
| 41% | ICET | 4 | One of the first musicians to have an "explicit content" sticker on an album |
| 41% | BYRD | 4 | "With ___ at the South Pole," first documentary to win an Oscar (for cinematography) |
| 41% | LUISE | 5 | ___ Rainer, the first person to win back-to-back Oscars |
| 40% | MARIE | 5 | First name of the first woman to win a Nobel Prize |
| 40% | BARDEM | 6 | Javier __, first Spanish actor to win an Oscar |
| 40% | ANG | 3 | Lee who was the first Asian to win a best-director Oscar |
| 39% | POITIER | 7 | Sidney who was the first African-American to win a Best Actor Oscar |
| 39% | POITIER | 7 | Sidney who was the first African American to win a Best Actor Oscar |
| 39% | RATEDR | 6 | Like eight of the past ten films to win the Best Picture Oscar |
| 39% | JANNINGS | 8 | Emil __, first man to win an Oscar for Best Actor |