| 100% | DANTE | 5 | “Aristotle and ___ Discover the Secrets of the Universe” (award-winning Y.A. book by Benjamin Alire Sáenz) |
| 42% | LANE | 4 | "The Ocean at the End of the ___," 2013 novel by Neil Gaiman featuring an unnamed protagonist that won a British Book Award |
| 40% | PRIZES | 6 | Awards won by best books of the years, e.g. Orange |
| 39% | ANYTHINGGOES | 12 | 1934 show with music and lyrics by 39-Across whose 1987 and 2011 revivals both won the Tony Award for Best Revival of a Musical (2 wds.) |
| 37% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 37% | TALES | 5 | & 14D 1997 Whitbread Book of the Year Award-winning volume by Ted Hughes |
| 37% | SIGN | 4 | "___ of the Times," hit song by Harry Styles which won a Brit Award in 2018 |
| 37% | BESTMUSICAL | 11 | Award won by the starts of 17-, 25-, 39- and 52-Across and 11- and 29-Down |
| 36% | MARGARET | 8 | ___ Mitchell, novelist whose only novel "Gone with the Wind" won her a Pulitzer and a National Book Award |
| 36% | YIYUN | 5 | Li who won the PEN/Faulkner Award for Fiction for “The Book of Goose,” about a literary hoax concocted by two French teen-agers in the nineteen-fifties (April, 2023) |
| 36% | JASONMOTT | 9 | Writer whose novel "Hell of a Book" won the 2021 National Book Award for Fiction (2 wds.) |
| 36% | JASONMOTT | 9 | Author who won the 2021 National Book Award for Fiction for "Hell of a Book": 2 wds. |
| 36% | THESEAAROUNDUS | 14 | 44-Across book about the science and history of the ocean that won the 1952 National Book Award for Nonfiction (4 wds.) |
| 35% | JESMYNWARD | 10 | Author whose novels "Salvage the Bones" and "Sing, Unburied, Sing" each won a National Book Award: 2 wds. |
| 35% | RACHELCARSON | 12 | "Silent Spring" writer and namesake of the international environmental award won by 32-Across in 2019 (2 wds.) |
| 35% | 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. |
| 35% | HOLYGHOST | 9 | Book by John Sandford which was part of the "Virgil Flowers" novel series and became a NYT 2018 Bestseller: 2 wds. |
| 35% | ELEVENRINGS | 11 | "___: The Soul of Success," a book by Phil Jackson, the legendary coach of Chicago Bulls and LA Lakers: 2 wds. |
| 35% | GRAMMY | 6 | Song of the Year award won by Lorde for 36-Across |
| 34% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 34% | OBIES | 5 | Pair of awards won by A Strange Loop |
| 34% | THEEMISSARY | 11 | Book that won the 2018 National Book Award for Translated Literature, written by Yoko Tawada and translated by Margaret Mitsutani: 2 wds. |
| 34% | RAIN | 4 | "___ On Me," song by Lady Gaga and Ariana Grande that won the MTV Video Music Award for Song of the Year in 2020 |
| 33% | TONYS | 5 | Awards won by the musicals "Hamilton" and "Hadestown" |
| 33% | PEOPLE | 6 | "How to Win Friends and Influence ___," self-help book written by Dale Carnegie which is one of the best-selling books of all time |
| 33% | NOBODY | 6 | The Diary of a __, humorous book by the Grossmiths |
| 33% | BADROMANCE | 10 | A 2009 hit by Lady Gaga which won two Grammys and has gone on to become one of the best selling singles of all time: 2 wds |
| 33% | JANEHARPER | 10 | 18-Across and 33-Across writer whose novel "The Dry" won the British Book Award for Crime & Thriller Book of the Year 2018 (2 wds.) |
| 33% | CHRISSTAPLETON | 14 | "From a Room: Volume 1" singer who won the 2017 CMA Awards for Male Vocalist of the Year and Album of the Year (2 wds.) |
| 33% | WALTLONGMIRE | 12 | Sheriff of the fictional county of Absaroka, Wyoming, who is featured in 20 books by 40-Across and a 2012-2017 television series (2 wds.) |