| 100% | THECONTINENTAL | 14 | First song to win an Oscar, 1934 (written by Con Conrad) |
| 53% | EMINEM | 6 | First rapper to win an Oscar for Best Original Song |
| 46% | GODFATHER | 9 | First sequel to win an Oscar for Best Picture |
| 45% | SHREK | 5 | First film to win an Oscar for Best Animated Feature |
| 45% | ADELE | 5 | First songwriter to win an Oscar for a James Bond theme |
| 42% | MORENO | 6 | First Hispanic actress to win an Oscar, Rita __ |
| 42% | MCDANIEL | 8 | First Black actress to win an Oscar, Hattie __ |
| 42% | JANNINGS | 8 | Emil __, first man to win an Oscar for Best Actor |
| 42% | EMINEM | 6 | First rapper to win a Best Original Song Oscar |
| 40% | SPANISH | 7 | Penelope Cruz, first __ actress to win an Oscar |
| 39% | BARDEM | 6 | Javier __, first Spanish actor to win an Oscar |
| 38% | ACT | 3 | One way to win an Oscar |
| 38% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 38% | MATLIN | 6 | Only deaf performer to win an Oscar |
| 37% | SHAW | 4 | Only Literature Nobelist also to win an Oscar |
| 37% | VIOLA | 5 | ___ Davis, first black actress to win an Oscar, Emmy and Tony |
| 36% | ALI | 3 | Mahershala who was the first Muslim performer to win an Oscar |
| 36% | ALI | 3 | Mahershala who was the first Muslim actor to win an Oscar |
| 36% | OTOOLE | 6 | Most-nominated Best Actor (eight times) never to win an Oscar |
| 36% | DANICAPATRICK | 13 | First woman to win an IndyCar event: 2 wds. |
| 35% | BYRD | 4 | "With ___ at the South Pole," first documentary to win an Oscar (for cinematography) |
| 35% | CATEBLANCHETT | 13 | Only person to win an Oscar for playing an Oscar-winning actress |
| 35% | VIOLADAVIS | 10 | Only African-American to win an Oscar, Tony and Emmy for acting |
| 35% | THEARTIST | 9 | Only French-produced film to win an Oscar for Best Picture (2011) |
| 35% | TWEETY | 6 | "Headliner" of the first Warner Bros. short to win an Oscar |
| 35% | INEED | 5 | "___ to Wake Up," 2006 Oscar-winning song by Melissa Etheridge |
| 35% | BIGELOW | 7 | First female to win best director Oscar |
| 34% | VITO | 4 | First role to win two acting Oscars |
| 34% | FOSSE | 5 | Only person to win an Oscar, Emmy and Tony in the same year (1973) |
| 34% | OURHOUSE | 8 | Song written by Graham Nash called “an ode to countercultural domestic bliss” |