| 100% | PLANA | 5 | The first thing to try (and hope for the best) |
| 55% | SIDNEY | 6 | Actor and director Poitier, the first black person to win an Oscar for best actor |
| 54% | DIAS | 4 | Bartolomeu ___, maritime explorer and first European to round the Cape of Good Hope |
| 51% | 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.) |
| 49% | ANG | 3 | ___ Lee, first Asian to win the Oscar for Best Director |
| 49% | CLASS | 5 | Remember the first time you were chosen as the ___ monitor (student leader) and got to be in charge for the day? Best. Day. Ever! |
| 48% | 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.) |
| 47% | DIAS | 4 | First to round the Cape of Good Hope |
| 46% | XXXXX | 5 | First thing to try |
| 46% | PRAY | 4 | Hope for the best |
| 46% | PRAYED | 6 | Hoped for the best |
| 46% | PUNS | 4 | The salon names To Dye For and Best Little Hairhouse (both real!), e.g. |
| 46% | LIUCIXIN | 8 | Author who, in 2015, became the first Asian to win the Hugo Award for Best Novel, for “The Three-Body Problem” |
| 45% | HALLEBERRY | 10 | First African-American to win the Oscar for Best Actress |
| 45% | NTAMACK | 7 | Emile —, France and Toulouse rugby union wing; first player to score a try in the Heineken Cup |
| 45% | INDIEGOGO | 9 | Online platform that was one of the first websites to offer crowdfunding for business and personal goals |
| 45% | CARDI | 5 | ___ B, hip hop star who became the first female rapper to win a Grammy for Best Rap Album |
| 45% | RITE | 4 | Learning to read and w___ is one of the first things taught in school |
| 44% | HALLEBERRY | 10 | First Black woman to win the Oscar for Best Actress: 2 wds. |
| 44% | LOSEYOURSELF | 12 | First rap track to win the Academy Award for Best Original Song |
| 44% | SYNC | 4 | Good thing for a film's audio and video to be in |
| 44% | EDIT | 4 | Change ... one hopes for the better |
| 44% | OAHU | 4 | Hawaiian island that is home to Honolulu and was the setting for "50 First Dates" |
| 44% | SIDNEYPOITIER | 13 | First black person to win the Academy Award for Best Actor: 2 wds. |
| 44% | ASEPARATION | 11 | 2011 family drama that was the first Iranian film to win an Oscar for Best Foreign Language Film (2 wds.) |
| 43% | ULLMANN | 7 | Liv —, Best Actress in a Leading Role Oscar nominee for Face to Face and The Emigrants |
| 43% | HOME | 4 | "Fun ___," Broadway play with the first female writing team to win the Tony Award for Best Score |
| 43% | AMBITIONS | 9 | Hopes and aspirations for the future |
| 42% | YENTL | 5 | Movie for which Barbra Streisand became the first ever woman to receive a Golden Globe as Best Director |
| 42% | LALALAND | 8 | 2016 Best Picture (no, wait; it wasn't!) ... and a fitting place for the answers to starred clues? |