| 100% | JOHNCROWLEY | 11 | Author whose short story "Spring Break" won the 2018 Edgar Award in the Best Short Story category: 2 wds. |
| 74% | JASONREYNOLDS | 13 | Author whose novel "Long Way Down" won the 2018 Edgar Award in the Best Young Adult category: 2 wds. |
| 72% | ANNAMAZZOLA | 11 | Author whose novel "The Unseeing" won the 2018 Edgar Award in the Best Paperback Original category: 2 wds. |
| 48% | STEPHENKING | 11 | "Carrie" author who won a 1996 O. Henry Award for his short story "The Man in the Black Suit": 2 wds. |
| 48% | ALICEMUNRO | 10 | Canadian short story author who won the 2013 Nobel Prize in Literature: 2 wds. |
| 45% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 44% | KATRINALENK | 11 | 30-Across singer/actress who won the 2018 Tony Award for Best Actress in a Musical (2 wds.) |
| 44% | TAYLORSWIFT | 11 | "Love Story" singer-songwriter who won the award for Top Female Artist in Billboard 2018: 2 wds. |
| 44% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 44% | FORTUNESMILES | 13 | Adam Johnson short story collection that won the National Book Award for Fiction in 2015 (2 wds.) |
| 44% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 44% | ALEXBERENSON | 12 | Novelist whose "The Faithful Spy" won the 2007 Edgar Award for Best First Novel (2 wds.) |
| 43% | BRUCEDESILVA | 12 | Novelist whose "Rogue Island" won the 2011 Edgar Award for Best First Novel (2 wds.) |
| 43% | JASONMATTHEWS | 13 | Novelist whose "Red Sparrow" won the 2014 Edgar Award for Best First Novel (2 wds.) |
| 42% | MICHELLEZAUNER | 14 | Singer whose memoir "Crying in H Mart" won the 2021 Goodreads Choice Award for Best Memoir & Autobiography (2 wds.) |
| 42% | GABRIELLEZEVIN | 14 | 16-Across and 28-Across writer whose novel "Tomorrow, and Tomorrow, and Tomorrow" won the Goodreads Choice Award Winner for Best Fiction in 2022 (2 wds.) |
| 41% | AIMEEMANN | 9 | Former 'Til Tuesday lead singer whose "Mental Illness" won Best Folk Album at the 2018 Grammy Awards (2 wds.) |
| 41% | EBONYFLOWERS | 12 | Writer/artist who won the 2020 Eisner Award for Best Short Story for "Hot Comb" (2 wds.) |
| 41% | ISME | 4 | "This ___," Keala Settle song that won the 2018 Golden Globe Award for Best Original Song: 2 wds. |
| 41% | NEILGAIMAN | 10 | "American Gods" novelist who won the 2018 Audie Award for Narration by the Author for his story collection "Norse Mythology" (2 wds.) |
| 41% | SIGRIDNUNEZ | 11 | "Salvation City" author whose "The Friend" won the 2018 National Book Award for Fiction (2 wds.) |
| 40% | STEVEMARTIN | 11 | "L.A. Story" actor whose "The Crow: New Songs for the 5-String Banjo" won the Best Bluegrass Album Grammy in 2010: 2 wds. |
| 40% | THEWEEKND | 9 | Singer with an oddly spelled name whose "Starboy" won Best Urban Contemporary Album at the 2018 Grammy Awards (2 wds.) |
| 40% | ALICEWALKER | 11 | "The Color Purple" author who won a 1986 O. Henry Award for her short story "Kindred Spirits": 2 wds. |
| 40% | LOUISEERDRICH | 13 | "The Round House" author who won a 1987 O. Henry Award for her short story "Fleur": 2 wds. |
| 40% | WONDERWOMAN | 11 | Superhero film by Patty Jenkins that won the 2018 Hugo Award for Best Dramatic Presentation: 2 wds. |
| 40% | FOOFIGHTERS | 11 | Band whose "Run" won the 2018 Grammy for Best Rock Song: 2 wds. |
| 39% | ALLISONJANNEY | 13 | She won the 2018 SAG Award for Female Actor in a Supporting Role for "I, Tonya": 2 wds. |
| 39% | RODDYRICCH | 10 | "The Box" rapper who won the BET Award for Best New Artist in 2020: 2 wds. |
| 39% | NEILGAIMAN | 10 | Author whose YA novel "The Graveyard Book" won the Newbery Medal in 2009: 2 wds. |