| 100% | 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.) |
| 59% | 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.) |
| 51% | LUPITANYONGO | 12 | Actress who won an Oscar for her first feature film role, in "12 Years a Slave": 2 wds. |
| 51% | LUPITA | 6 | With 18-Across, Kenyan-Mexican actress who won an Oscar for "12 Years a Slave" |
| 49% | 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.) |
| 48% | CATEBLANCHETT | 13 | "Blue Jasmine" and "The Aviator" star who was the first Australian to win Oscars in two acting categories (2 wds.) |
| 48% | ACADEMYAWARDS | 13 | 18-Across and 42-Across were the first Spanish actress and actor to win these honors: 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.) |
| 46% | LUPITANYONGO | 12 | Mexico-born actress who won an Oscar for her role in "12 Years a Slave": 2 wds. |
| 46% | 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.) |
| 45% | TONIMORRISON | 12 | "Beloved" author who died August 5, and who was the first African-American woman to win a Nobel Prize: 2 wds. |
| 45% | NICOLEKIDMAN | 12 | Actress who won an Oscar for Best Actress for "The Hours" and a Worst Screen Couple Razzie Award with Will Ferrell for "Bewitched": 2 wds. |
| 45% | ETHELWATERS | 11 | Harlem Renaissance singer and actress who was the first African American to star in her own TV show: 2 wds. |
| 44% | 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.) |
| 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. |
| 43% | LUPITANYONGO | 12 | Actress who won a Best Supporting Actress Oscar for her first role in a feature film (Patsey in 2013's "12 Years a Slave") (2 wds.) |
| 43% | JESSICALANGE | 12 | Actress who was nominated for an Emmy for playing 18-Across and for an Oscar for playing 32-Across (2 wds.) |
| 42% | STEFFIGRAF | 10 | Tennis player who is the only player (man or woman) to win a Grand Slam and Olympic gold medal in one year: 2 wds. |
| 42% | SHOHEIOHTANI | 12 | Japanese MLB player who was the first player in history to be a pitcher and hitter in the All-Star Game, in 2021: 2 wds. |
| 42% | CAROLEKING | 10 | "You've Got a Friend" singer/pianist who was the first woman to win a Grammy for Song of the Year (2 wds.) |
| 42% | LILLIANGISH | 11 | "The Birth of a Nation" star who is the only silent era actor to win the AFI Life Achievement Award: 2 wds. |
| 42% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |
| 42% | MUHAMMADYUNUS | 13 | Social entrepreneur and economist who was the first Bangladeshi to win the Nobel Peace Prize: 2 wds. |
| 41% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 41% | LUPITANYONGO | 12 | "12 Years a Slave" actress who debuted as pirate Maz Kanata in "Star Wars: The Force Awakens": 2 wds. |
| 41% | ALTHEAGIBSON | 12 | Tennis great who was the first person of color to win a Wimbledon championship (2 wds.) |
| 41% | WAYNEGRETZKY | 12 | Hockey legend who was the first since Bobby Orr to tally 100+ assists in a season, and did so 11 times: 2 wds. |
| 41% | CHLOEZHAO | 9 | 16-Across director who won an Academy Award for Best Director in 2021, becoming the first non-white woman to win a directing Oscar (2 wds.) |
| 41% | MANUGINOBILI | 12 | NBA star from Argentina who is one of only two players to win a EuroLeague title, an NBA championship, and an Olympic gold medal (2 wds.) |
| 41% | SANDRABULLOCK | 13 | Actress who won an Oscar for Best Actress for "The Blind Side" and a Worst Actress Razzie Award for "All About Steve": 2 wds. |