| 100% | PENN | 4 | Two-time Best Actor winner Sean |
| 90% | PENN | 4 | Two-time Best Actor Oscar winner Sean |
| 77% | THANKSINADVANCE | 15 | Two-time Best Actor winner arriving early? |
| 73% | WALTZ | 5 | Two-time Best Supporting Actor Oscar winner Christoph |
| 73% | SEAN | 4 | Two-time Best Actor Oscar winner Penn |
| 71% | TOMHANKSGIVING | 14 | Charity from a two-time Best Actor winner? |
| 64% | ALDA | 4 | Two-time Emmy winner as best actor in a comedy |
| 64% | MAHERSHALAALI | 13 | Two-time Best Supporting Actor Oscar winner who plays Wayne Hayes in season 3 of 43-Across (2 wds.) |
| 62% | HANKS | 5 | Winner of two consecutive Best Actor Oscars |
| 59% | ALI | 3 | Two-time Best Supporting Actor Mahershala |
| 59% | PENN | 4 | Two-time Oscar-winning actor Sean |
| 58% | ENO | 3 | Two-time Best Rock Album Grammy winner |
| 58% | ANG | 3 | Two-time Best Director Oscar winner ___ Lee |
| 58% | ANG | 3 | Two-time Best Director Oscar winner Lee |
| 58% | MERYL | 5 | Two-time Best Actress Oscar winner Streep |
| 58% | LEE | 3 | Two-time Best Director Oscar winner Ang |
| 58% | GOULET | 6 | Robert —, 1968 Best Actor in a Musical Tony Award winner for The Happy Time |
| 58% | LYDIA | 5 | Two-time Best Female Golfer ESPY winner Ko |
| 58% | INARRITU | 8 | Two-time Best Director Oscar winner Alejandro González __ |
| 57% | BRANDO | 6 | Two-time Best Actor, 1954 and 1972 |
| 57% | MALEK | 5 | Best Actor winner Rami |
| 57% | RAMI | 4 | Best Actor winner Malek |
| 57% | ADRIEN | 6 | Best Actor winner Brody |
| 57% | LLOYD | 5 | Frank ___, two-time Best Director Oscar winner |
| 56% | FOXX | 4 | Best Actor winner for "Ray" |
| 56% | MARIOPUZO | 9 | Two-time Oscar winner for Best Adapted Screenplay |
| 55% | ANG | 3 | Two-time Best Director winner Lee |
| 55% | SWANK | 5 | Two-time Best Actress winner Hilary |
| 55% | LUISE | 5 | Two-time Best Actress winner Rainer |
| 55% | MALEK | 5 | Best Actor winner for "Bohemian Rhapsody" |