| 100% | SALLY | 5 | I wrote "Conversations with Friends" and won the Sunday Times Young Writer of the Year |
| 44% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 41% | SAM | 3 | ___ Smith, "Stay With Me" singer who was 22 when they won the 2015 Grammy for Record of the Year |
| 41% | 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 |
| 39% | LEES | 4 | A Z —, Durham and former Yorkshire batsman; 2014 Cricket Writers' Club Young Cricketer of the Year |
| 38% | NOBEL | 5 | With 32- and 38-Across, 2014 honor won by the writer of 15-Across |
| 38% | SPRING | 6 | I'm the time of year for cleaning and picnics |
| 38% | JORDAN | 6 | With 33-Across, golfer who won both PGA Tour Player of the Year and Rookie of the Year awards |
| 38% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 38% | FALL | 4 | I'm the time of year for apple-picking and leaf-raking |
| 37% | WINTER | 6 | I'm the time of year for cozy clothes and sipping hot chocolate |
| 37% | JUSTIN | 6 | With 35-Across, "Yummy" singer who won the Pop Album of the Year Juno in 2011 and 2016 |
| 37% | MELANIA | 7 | “___ and Me,” book sourced in part from surreptitious recordings of conversations with the First Lady (September, 2020) |
| 37% | TIAREJENNINGS | 13 | Softball player who won two championships with the University of Oklahoma and who was named Big 12 Freshman of the Year in 2021 (2 wds.) |
| 37% | MONSOON | 7 | I'm the time of year for donning umbrellas and dancing in the rain |
| 37% | LUTHERVANDROSS | 14 | His "Dance With My Father" won the 2003 Grammy for Song of the Year |
| 37% | OBAMA | 5 | Time's Person of the Year for 2008 and 2012 |
| 37% | DENG | 4 | Time's Man of the Year for 1978 and 1985 |
| 37% | GRETA | 5 | ___ Thunberg, Time's youngest Person of the Year |
| 36% | VOLODYMYR | 9 | With 27 Across, Time's Person of the Year of 2022 |
| 36% | BAD | 3 | With 7-Down, Billie Eilish hit that won the 2020 Grammy for Song of the Year |
| 36% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 36% | LEES | 4 | Alex —, 2014 Cricket Writers' Club Young Cricketer of the Year |
| 36% | LIZZO | 5 | "About Damn Time" female singer who won the 2023 Grammy for Record of the Year |
| 35% | LEES | 4 | A Z —, 2014 Cricket Writers' Club Young Cricketer of the Year |
| 35% | STEVIE | 6 | With 31-Across, "Sir Duke" singer who won the 1977 Grammy for Producer of the Year, Non-Classical |
| 35% | LEAVETHE | 8 | With 32-Across, Silk Sonic single that won the 2022 Grammy for Song of the Year: 2 wds. |
| 35% | LADYGAGA | 8 | "Rain on Me" singer who won the MTV Tricon Award, Artist of the Year, and two other awards at the 2020 MTV Video Music Awards (2 wds.) |
| 35% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 35% | GRETA | 5 | ___ Thunberg, youngest Time Person of the Year |