| 100% | MAHERSHALAALI | 13 | Actor whose role in 2018's "Green Book" is the longest Best Supporting Actor-winning performance (screen time 1:06:38): 2 wds. |
| 65% | ADRIENBRODY | 11 | Actor whose role in 2024's "The Brutalist" is the longest Best Actor-winning performance (screen time 2:08:30): 2 wds. |
| 56% | VIVIENLEIGH | 11 | Actress whose role in 1939's "Gone With the Wind" is the longest Best Actress-winning performance (screen time 2:23:32): 2 wds. |
| 40% | MAHERSHALAALI | 13 | Best Supporting Actor Oscar winner for the 2018 film "Green Book": 2 wds. |
| 40% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 40% | ALLISONJANNEY | 13 | She won the 2018 Oscar for Best Supporting Actress for her role in "I, Tonya": 2 wds. |
| 39% | ALLISONJANNEY | 13 | She won the 2018 SAG Award for Female Actor in a Supporting Role for "I, Tonya": 2 wds. |
| 39% | EMILYBLUNT | 10 | She won the 2019 Screen Actors Guild Award for Female Actor in a Supporting Role for "A Quiet Place": 2 wds. |
| 38% | MAHERSHALAALI | 13 | "Hidden Figures" actor who won the 2017 and 2019 Oscars for Best Supporting Actor ("Moonlight" and "Green Book"): 2 wds. |
| 37% | JASONREYNOLDS | 13 | Author whose novel "Long Way Down" won the 2018 Edgar Award in the Best Young Adult category: 2 wds. |
| 37% | BRADPITT | 8 | Best Supporting Actor Oscar winner for the 2019 film "Once Upon a Time in Hollywood": 2 wds. |
| 37% | GREENBOOK | 9 | Film for which 32-Across won the Best Supporting Actor Oscar in 2019: 2 wds. |
| 37% | SEANCONNERY | 11 | Actor born in Scotland who won the Academy Award for Best Supporting Actor for playing Jimmy Malone in "The Untouchables": 2 wds. |
| 36% | VIOLADAVIS | 10 | She won the 2017 Oscar for Best Supporting Actress for her role in "Fences": 2 wds. |
| 36% | CUBAGOODINGJR | 13 | Actor who won a Best Supporting Actor Oscar for his role in the 1996 film "Jerry Maguire" (3 wds.) |
| 36% | SAMROCKWELL | 11 | "Vice" actor who won the 2018 Oscar for Best Supporting Actor ("Three Billboards Outside Ebbing, Missouri"): 2 wds. |
| 35% | JOELGREY | 8 | "Wicked" actor who won the Best Supporting Actor Oscar for 1972's "Cabaret": 2 wds. |
| 35% | ALLISONJANNEY | 13 | Best Supporting Actress winner at the 2018 Critics' Choice Awards for her role in "I, Tonya": 2 wds. |
| 35% | VIOLADAVIS | 10 | She won the 2017 SAG Award for Female Actor in a Supporting Role for "Fences": 2 wds. |
| 35% | BRADPITT | 8 | Best Supporting Actor winner for 2019's "Once Upon a Time in Hollywood": 2 wds. |
| 35% | TOMHANKS | 8 | Best Supporting Actor nominee for 2019's "A Beautiful Day in the Neighborhood": 2 wds. |
| 35% | ANNAMAZZOLA | 11 | Author whose novel "The Unseeing" won the 2018 Edgar Award in the Best Paperback Original category: 2 wds. |
| 35% | JOHNBOYEGA | 10 | "Star Wars: The Force Awakens" actor whose latest role is as a security guard in "Detroit": 2 wds. |
| 35% | CHRISTIANBALE | 13 | Actor born in Wales who won the Academy Award for Best Supporting Actor for playing Dick Dicky Eklund in the movie "The Fighter": 2 wds |
| 35% | TIMOTHYHUTTON | 13 | Actor who won a Best Supporting Actor Oscar for his first role in a feature film (Conrad Jarrett in 1980's "Ordinary People") (2 wds.) |
| 35% | DALL | 4 | John —, Best Actor in a Supporting Role Oscar nominee for The Corn is Green |
| 34% | ACTORSGUILD | 11 | Screen ___ Awards, presented by the SAG-AFTRA, which Nicholson won for his role in "As Good As It Gets": 2 wds. |
| 34% | JOHNCROWLEY | 11 | Author whose short story "Spring Break" won the 2018 Edgar Award in the Best Short Story category: 2 wds. |
| 34% | OSCARISAAC | 10 | "Star Wars: The Rise of Skywalker" actor whose surname is a person in the book of Genesis: 2 wds. |
| 34% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |