| 100% | CMA | 3 | Org. that voted Keith Urban 2018 Entertainer of the Year |
| 63% | CMA | 3 | Group that named Keith Urban Entertainer of the Year in 2018: Abbr. |
| 49% | CMA | 3 | Entertainer of the Year org. |
| 48% | CMA | 3 | Org. that named Garth Brooks Entertainer of the Year six times |
| 45% | CMA | 3 | Group that voted Luke Combs its 2021 Entertainer of the Year: Abbr. |
| 43% | AVA | 3 | Director DuVernay who was awarded Entertainer of the Year at the 2018 NAACP Image Awards |
| 42% | CMA | 3 | Nashville org. that voted “Fast Car” its 2023 song of the year |
| 41% | CMA | 3 | Org. that awarded Taylor Swift "Entertainer of the Year" in 2009 and 2011 |
| 41% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 40% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 40% | CMA | 3 | Group that has named Garth Brooks Entertainer of the Year seven times (Abbr.) |
| 40% | CMA | 3 | Nashville org. that hasn’t named a female Entertainer of the Year since Taylor Swift, in 2011 |
| 39% | LAS | 3 | ___ Vegas Entertainer of the Year |
| 39% | CMA | 3 | Group that named Taylor Swift Entertainer of the Year twice (Abbr.) |
| 39% | ADS | 3 | Org. that names a "Word of the Year" |
| 38% | CMAS | 4 | Award show that has named Garth Brooks Entertainer of the Year six times, briefly |
| 38% | CMA | 3 | Group that named Luke Combs Entertainer of the Year in 2021 (Abbr.) |
| 38% | HARPERLEE | 9 | Author of the book that Times readers voted the best of the last hundred and twenty-five years |
| 38% | LIZZO | 5 | Singer named Time's 2019 Entertainer of the Year |
| 37% | LIZZO | 5 | Singer named Entertainer of the Year in 2019 by Time magazine |
| 36% | NBA | 3 | Sixth Man of the Year Award org. |
| 36% | LUKEBRYAN | 9 | "Strip It Down" singer and 2015 CMA Entertainer of the Year: 2 wds. |
| 35% | MONTHOFMAYBE | 12 | Part of the year that's filled with possibility? |
| 35% | THATSWHATILIKE | 14 | Bruno Mars song that won the 2018 Song of the Year Grammy (4 wds.) |
| 35% | CLEOPATRA | 9 | Only highest-grossing film of the year that lost money |
| 35% | CMAS | 4 | Awards show whose most recent female Entertainer of the Year was Taylor Swift, in 2011 |
| 35% | CAPOT | 5 | Horse of the Year that won the 1949 Preakness and Belmont |
| 34% | USAF | 4 | Org. that holds the annual Mustache March each year |
| 34% | CMA | 3 | Group that has named Garth Brooks its Entertainer of the Year a record seven times: Abbr. |
| 34% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |