| 100% | THEUNDEFEATED | 13 | Illustrated poetic tribute to Black Americans by Kwame Alexander and Kadir Nelson that won the 2020 Caldecott Medal (2 wds.) |
| 30% | FINDINGWINNIE | 13 | Children's book about the bear that inspired A.A. Milne by Lindsay Mattick and Sophie Blackall that won the 2016 Caldecott Medal (2 wds.) |
| 28% | THEEMISSARY | 11 | Book that won the 2018 National Book Award for Translated Literature, written by Yoko Tawada and translated by Margaret Mitsutani: 2 wds. |
| 26% | TREATMYSELF | 11 | 2020 studio album by 29-Across that features the hit singles "Nice to Meet Ya" and "No Excuses" (2 wds.) |
| 25% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 25% | SHANEBIEBER | 11 | Cleveland Indians starting pitcher who won the American League Triple Crown and the 2020 Cy Young Award (2 wds.) |
| 25% | INDUSTRYGAMES | 13 | Title track of the 2020 EP by 11-Down that also features 8-Down and 36-Down (2 wds.) |
| 25% | THEFRIEND | 9 | Book that won the 2018 National Book Award for Fiction, written by Sigrid Nunez: 2 wds. |
| 25% | MISSINGYOU | 10 | Tribute to Marvin Gaye written by Lionel Richie and sung by 50-Across that was a Top 10 hit in 1984 (2 wds.) |
| 25% | BACKHOME | 8 | "Bring Him ___," musical tribute to Nelson Mandela by Hugh Masekela: 2 wds. |
| 25% | WILTONGREGORY | 13 | First Black American cardinal, appointed by Pope Francis in 2020: 2 wds. |
| 25% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 25% | ALLYSONFELIX | 12 | American track and field sprinter who won the 2012 Olympic gold in 200 meters and has a total of 9 Olympic medals: 2 wds. |
| 24% | RADIANTCHILD | 12 | Picture book biography depicting the youth of artist Jean-Michel Basquiat by Javaka Steptoe that won the 2017 Caldecott Medal (2 wds.) |
| 24% | JIMTHORPE | 9 | Native American Olympic gold medalist and NFL All-Pro posthumously awarded the Presidential Medal of Freedom by Joe Biden: 2 wds. |
| 24% | LSUTIGERS | 9 | Team that defeated Clemson to win the 2020 NCAA FBS Championship Game, for short (2 wds.) |
| 24% | AARONRODGERS | 12 | Former Packers quarterback who won the 2011, 2014, 2020, and 2021 AP NFL MVP Awards: 2 wds. |
| 24% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 23% | BARRIERSTOENTRY | 15 | Impediments to newcomers, illustrated by black squares in rows 2, 4, 12 and 14 |
| 23% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 23% | WHITESOX | 8 | Chicago MLB team that won the World Series in 1906, 1917, and 2005 (2 wds.) |
| 23% | ALLYSONFELIX | 12 | Track and field athlete who won her record-setting 11th career medal at the 2020 Tokyo Olympics: 2 wds. |
| 23% | SOFIAKENIN | 10 | American tennis player who won the Australian Open in 2020: 2 wds. |
| 23% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 23% | JOHNVELAZQUEZ | 13 | Jockey who won the Kentucky Derby in 2011, 2017, and 2020 (2 wds.) |
| 22% | HOUSTONASTROS | 13 | Minute Maid Park team that won the 2022 World Series four games to two over the Philadelphia Phillies (2 wds.) |
| 22% | LSUTIGERS | 9 | Team that beat the Iowa Hawkeyes to win 2023 NCAA women's basketball championship, led by NCAA Tournament Most Outstanding Player Angel Reese (2 wds.) |
| 22% | ARCHIEGRIFFIN | 13 | Only player to win the 15-Across twice, in 1974 and 1975: 2 wds. |
| 22% | LOUISEGLUCK | 11 | American poet who won the 2020 Nobel Prize in Literature (2 wds.) |
| 22% | LOUISEGLUCK | 11 | American writer who won the 2020 Nobel Prize in Literature (2 wds.) |