| 100% | MAHERSHALAALI | 13 | First black actor to win two Oscars in the same category, and only the second to win two competitive Oscars: 2 wds. |
| 49% | CATEBLANCHETT | 13 | "Blue Jasmine" and "The Aviator" star who was the first Australian to win Oscars in two acting categories (2 wds.) |
| 43% | RAMIMALEK | 9 | Actor who became the first one of Egyptian heritage to win an Oscar for Best Actor in 2019: 2 wds. |
| 43% | HALLEBERRY | 10 | First Black woman to win the Oscar for Best Actress: 2 wds. |
| 42% | SIDNEY | 6 | Actor and director Poitier, the first black person to win an Oscar for best actor |
| 41% | SIDNEYPOITIER | 13 | First black person to win the Academy Award for Best Actor: 2 wds. |
| 41% | PAULSCHNEIDER | 13 | Actor who played the role of Mark Brendanawicz in "Parks and Recreation", a character that appeared only in the first two seasons: 2 wds. |
| 40% | MICHAELJORDAN | 13 | Shaquille, Willis Reed and ___, the only three to have won NBA MVP, All-Star game MVP, and Finals MVP awards in the same year: 2 wds. |
| 40% | GWENJORGENSEN | 13 | American distance runner and two-time ITU World Champion who was the first to win a triathlon gold for USA in the Olympics: 2 wds. |
| 40% | IGGYAZALEA | 10 | "Fancy" singer featured on "Problem" who in 2014 became the second ever to be simultaneously #1 and #2 with her first two hits: 2 wds. |
| 40% | FOSSE | 5 | Only person to win an Oscar, Emmy and Tony in the same year (1973) |
| 40% | JOAQUINPHOENIX | 14 | Actor who won an Oscar playing the Joker in 2019's "Joker," 11 years after Heath Ledger did the same: 2 wds. |
| 40% | 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. |
| 40% | GEOFFREYRUSH | 12 | "Shine" star who was the first Australian to be nominated for Oscars in two acting categories (2 wds.) |
| 39% | ARCHIEGRIFFIN | 13 | Only player to win the 15-Across twice, in 1974 and 1975: 2 wds. |
| 39% | SIDNEYPOITIER | 13 | 15-Across, 30-Across, and "Lilies of the Field" star who was the first Black man to win an Academy Award for Best Actor (2 wds.) |
| 38% | PHYLICIARASHAD | 14 | First Black performer to win a Tony Award for Lead Actress in a Play, for "A Raisin in the Sun" in 2004: 2 wds. |
| 38% | ACADEMYAWARDS | 13 | 18-Across and 42-Across were the first Spanish actress and actor to win these honors: 2 wds. |
| 38% | JASONROBARDS | 12 | He won two Best Supporting Actor Oscars, for "All the President's Men" and "Julia": 2 wds. |
| 38% | RITAMORENO | 10 | Actress who attended the 2018 Oscars in the same dress she wore to the 1962 Oscars, when she won Best Supporting Actress: 2 wds. |
| 38% | JOSECANSECO | 11 | Retired ballplayer who was the first to hit 40 homers and steal 40 bases in the same season: 2 wds. |
| 38% | 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.) |
| 38% | NATEROBINSON | 12 | Only player to win the NBA Slam Dunk Contest three times, in 2006, 2009, and 2010: 2 wds. |
| 37% | JONES | 5 | James Earl ___, actor and first African-American man to win the Tony Award in the Leading Actor category |
| 37% | KURTWARNER | 10 | Undrafted quarterback who won two MVP awards and led the St. Louis Rams to a win in the 2000 Super Bowl: 2 wds. |
| 37% | BJORNBORG | 9 | One of only two players in the modern era to win five straight 17-Across Gentlemen's Singles Finals (1976-1980): 2 wds. |
| 37% | ROGERFEDERER | 12 | One of only two players in the modern era to win five straight 17-Across Gentlemen's Singles Finals (2003-2007): 2 wds. |
| 37% | KOBEBRYANT | 10 | LA Lakers legend fondly remembered as "Black Mamba" who is the only player in NBA history to have two jersey numbers retired by the same team: 2 wds. |
| 36% | JAMESEARLJONES | 14 | First Black performer to win a Tony Award for Lead Actor in a Play, for "The Great White Hope" in 1969: 3 wds. |
| 36% | BRYANCRANSTON | 13 | "Breaking Bad" actor who won two Tony Awards for Best Actor in a Play, for "All the Way" and "Network" (2 wds.) |