| 100% | ACADEMYAWARDS | 13 | 18-Across and 42-Across were the first Spanish actress and actor to win these honors: 2 wds. |
| 55% | LUPITANYONGO | 12 | "12 Years a Slave," 18-Across, and 32-Across star who was the first Kenyan-Mexican actress to win an Oscar (2 wds.) |
| 54% | ESPYAWARD | 9 | Ronda Rousey is the first mixed martial artist to win this athletic honor: 2 wds. |
| 49% | SAMINNOSRAT | 11 | Chef and cookbook writer whose four elements of cooking are the first words of the answers to 16-Across, 18-Across, 42-Across, and 45-Across (2 wds.) |
| 48% | MUHAMMADYUNUS | 13 | Social entrepreneur and economist who was the first Bangladeshi to win the Nobel Peace Prize: 2 wds. |
| 47% | 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.) |
| 45% | TONIMORRISON | 12 | "Beloved" author who died August 5, and who was the first African-American woman to win a Nobel Prize: 2 wds. |
| 44% | MAHERSHALAALI | 13 | First black actor to win two Oscars in the same category, and only the second to win two competitive Oscars: 2 wds. |
| 44% | 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.) |
| 44% | ETHELWATERS | 11 | Harlem Renaissance singer and actress who was the first African American to star in her own TV show: 2 wds. |
| 43% | CATEBLANCHETT | 13 | "Blue Jasmine" and "The Aviator" star who was the first Australian to win Oscars in two acting categories (2 wds.) |
| 43% | INVENTINGANNA | 13 | Shonda Rhimes miniseries starring 18-Across and 42-Across based on the true story of a con artist who pretended to be an heiress (2 wds.) |
| 43% | HARLANCOBEN | 11 | 17-Across and 30-Across novelist who is the first writer to win an Anthony Award, a Shamus Award, and an Edgar Award (2 wds.) |
| 43% | 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. |
| 42% | CANDICEBERGEN | 13 | Actress who was the first woman to host "Saturday Night Live," and the first woman to host five times (2 wds.) |
| 42% | EDITHWHARTON | 12 | 13-Across and 25-Across writer who was the first woman to win a Pulitzer Prize in Literature, for her 1920 novel "The Age of Innocence" (2 wds.) |
| 41% | AMELIAEARHART | 13 | Aviation pioneer who was the first woman to fly solo across the Atlantic: 2 wds. |
| 41% | CHRISTIANBALE | 13 | He won the Oscar and Golden Globe for Best Supporting Actor for 18-Across: 2 wds. |
| 41% | MELISSALEO | 10 | She won the Oscar and Golden Globe for Best Supporting Actress for 18-Across: 2 wds. |
| 41% | TENZINGYATSO | 12 | 14th Dalai Lama who was the first Tibetan to win the Nobel Peace Prize: 2 wds. |
| 41% | ROSIEODONNELL | 13 | "The Flintstones" actress and comedian who won $500,000 for charity on "Who Wants to Be a Millionaire" in 2000: 2 wds. |
| 41% | ANDREAMCARDLE | 13 | Tony-nominated actress who was the first to play 40-Across on Broadway (2 wds.) |
| 41% | RAMIMALEK | 9 | Actor who became the first one of Egyptian heritage to win an Oscar for Best Actor in 2019: 2 wds. |
| 41% | JEFFDANIELS | 11 | Actor who won a 2013 Emmy for playing Will McAvoy, the anchor and managing editor on 37-Across: 2 wds. |
| 40% | TINAFEY | 7 | Actress/writer who was the first woman to be head writer of "Saturday Night Live," and the third woman to host five times (2 wds.) |
| 40% | HALLEBERRY | 10 | First Black woman to win the Oscar for Best Actress: 2 wds. |
| 40% | NORMMACDONALD | 13 | Deadpan comic and voice actor who was the "Weekend Update" anchor from 1994 to 1997: 2 wds. |
| 40% | SIDNEYPOITIER | 13 | First black person to win the Academy Award for Best Actor: 2 wds. |
| 40% | WOLESOYINKA | 11 | Nigerian playwright and novelist who was the first African honored with the Nobel Prize in Literature (2 wds.) |
| 39% | JENNIFERLOPEZ | 13 | 15-Across and 27-Across singer who was the first woman honored with a "Billboard" Icon Award (2 wds) |