| 100% | NNEDIOKORAFOR | 13 | 15-Across and 32-Across novelist who won a Hugo Award and a Nebula Award for "Binti" (2 wds.) |
| 80% | NNEDIOKORAFOR | 13 | African-American sci-fi novelist who won a Hugo Award and a Nebula Award for Best Novella (2 wds.) |
| 64% | URSULAKLEGUIN | 13 | American novelist who won eight Hugo Awards and six Nebula Awards in a writing career that spanned six decades (4 wds.) |
| 63% | OCTAVIABUTLER | 13 | African-American sci-fi novelist who won two Hugo Awards and two Nebula Awards (2 wds.) |
| 61% | ANNEMCCAFFREY | 13 | Novelist who won a Nebula Award for "Dragonrider" (2 wds.) |
| 54% | WILLIAMSTYRON | 13 | Novelist who won the National Book Award for Fiction for 15-Across (2 wds.) |
| 54% | TONIMORRISON | 12 | 18-Across and 32-Across novelist who won the 1993 Nobel Prize for Literature (2 wds.) |
| 54% | SAMUELRDELANY | 13 | Novelist who won Nebula Awards for "Babel-17" and "The Einstein Intersection" (3 wds.) |
| 53% | CHARLIZETHERON | 14 | 15-Across and 29-Across star who won a Best Actress Oscar for "Monster" and who turns 45 today (2 wds.) |
| 53% | SUSANCHOI | 9 | 15-Across and 33-Across writer who won the 2019 National Book Award for Fiction for her novel "Trust Exercise" (2 wds.) |
| 53% | JAMESMCBRIDE | 12 | 15-Across and 47-Across writer who won the 2013 National Book Award for Fiction for "The Good Lord Bird" (2 wds.) |
| 52% | ANGELINAJOLIE | 13 | Actress who won a Golden Globe, SAG Award, and Oscar for "Girl, Interrupted": 2 wds. |
| 52% | SYLVIAPLATH | 11 | American poet and novelist who won a posthumous Pulitzer Prize for "The Collected Poems" in 1982: 2 wds. |
| 52% | SANDRABULLOCK | 13 | Actress who won a Golden Globe, SAG Award, and Oscar for "The Blind Side": 2 wds. |
| 52% | EMILYHENRY | 10 | 18-Across, 26-Across, and 35-Across novelist who won the 2021, 2022, and 2023 Goodreads Choice Award for Best Romance (2 wds.) |
| 52% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 50% | ANNPATCHETT | 11 | 15-Across and 43-Across writer who won the Orange Prize for Fiction and the PEN/Faulkner Award for Fiction for "Bel Canto" (2 wds.) |
| 50% | DAVIDOYELOWO | 12 | 19-Across and 33-Across actor who won a 2015 NAACP Image Award for his portrayal of Martin Luther King Jr. in "Selma" (2 wds.) |
| 50% | AUDREYHEPBURN | 13 | Actress who won a Golden Globe for "Roman Holiday" and won their Cecil B. DeMille Award in 1990: 2 wds. |
| 49% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 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.) |
| 49% | JODIEFOSTER | 11 | Actress who won a Golden Globe for "The Silence of the Lambs" and won their Cecil B. DeMille Award in 2013: 2 wds. |
| 48% | JUDITHLIGHT | 11 | "Who's the Boss?" actress who won a Tony Award for "Other Desert Cities": 2 wds. |
| 48% | JAMESEARLJONES | 14 | "Coming 2 America" actor who won two Tony Awards for Best Actor in a Play, for "The Great White Hope" and "Fences" (3 wds.) |
| 48% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |
| 47% | JASONALEXANDER | 14 | "Seinfeld" actor who won a Tony Award for "Jerome Robbins' Broadway": 2 wds. |
| 47% | LIZAMINNELLI | 12 | Actress who won an Oscar for Best Actress for "Cabaret" and a Worst Actress Razzie Award for "Rent-a-Cop": 2 wds. |
| 47% | CHASEHEADLEY | 12 | Yankees third baseman who, in 2012, won a Gold Glove, a Silver Slugger Award and was also the NL RBI leader, playing for the Padres : 2 wds. |
| 47% | AUDRAMCDONALD | 13 | "Private Practice" actress who won a record-breaking sixth Tony Award in 2014 for her performance in "Lady Day at Emerson's Bar and Grill": 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.) |