| 100% | THEYEAR | 7 | "Man of ___" (Annual award): 2 wds. |
| 84% | IMA | 3 | "___ man of my word": 2 wds. |
| 84% | MALCOLMBROGDON | 14 | NBA guard who won the 2022-2023 Sixth Man of the Year award while with the Boston Celtics: 2 wds. |
| 79% | LIBERTYMEDAL | 12 | Annual award bestowed by the National Constitution Center to recognize leadership in the pursuit of freedom (2 wds.) |
| 74% | HASBEEN | 7 | "He ___ a man of great fortitude throughout his life": 2 wds. |
| 72% | WALTER | 6 | ___ Payton Man of the Year, annual award presented to a philanthropic NFL player |
| 72% | AMA | 3 | "I ___ Man of Constant Sorrow" ("O Brother, Where Art Thou?" song): 2 wds. |
| 72% | DAKPRESCOTT | 11 | Dallas Cowboys quarterback who won the 2022 Walter Payton NFL Man of the Year award: 2 wds. |
| 71% | AMA | 3 | "I ___ Man of Constant Sorrow" (song in "O Brother, Where Art Thou?"): 2 wds. |
| 68% | SPIKELEE | 8 | Director of "Inside Man": 2 wds. |
| 65% | NOBELPRIZE | 10 | Annual award given to outstanding achievers, which was presented to Obama, whose birthday it is today, in the Peace category: 2 wds. |
| 65% | AMA | 3 | "I ___ Man of Constant Sorrow" (Soggy Bottom Boys song) (2 wds.) |
| 63% | DIANAGABALDON | 13 | Award-winning writer of 29-Across (2 wds.) |
| 62% | DAKPRESCOTT | 11 | Dallas Cowboys quarterback who won the 2022 Walter Payton NFL Man of the Year Award (2 wds.) |
| 62% | ISEE | 4 | 2 wds to show understanding of something |
| 61% | GOLDSTAR | 8 | Kindergarten award: 2 wds. |
| 60% | OSCAR | 5 | Annual award that's an anagram of 1-Across |
| 60% | NBA | 3 | Sixth Man of the Year Award org. |
| 59% | LITTLEBIGTOWN | 13 | "Better Man" singers who have won the Country Music Association Award for Vocal Group of the Year six times (3 wds.) |
| 58% | GOLDGLOVE | 9 | Fielder's award: 2 wds. |
| 58% | NBA | 3 | Org. with a Sixth Man of the Year Award |
| 57% | NEBULA | 6 | Annual award presented by the Science Fiction and Fantasy Writers of America |
| 56% | KURTWARNER | 10 | Arizona Cardinals quarterback awarded the Walter Payton NFL Man of the Year Award in 2008 (2 wds.) |
| 56% | BEVERLYCLEARY | 13 | Award-winning author of books for kids: 2 wds. |
| 56% | MECCA | 5 | Annual destination of about 2.5 million pilgrims |
| 56% | ELI | 3 | 2-time Super Bowl MVP Award winner Manning |
| 56% | ZACBROWNBAND | 12 | "My Old Man" singers who have been nominated for the Country Music Association Award for Vocal Group of the Year 14 times (3 wds.) |
| 56% | DON | 3 | Actor Cheadle of "Iron Man 2" |
| 56% | TIECLIP | 7 | Men's neckwear accessory: 2 wds. |
| 55% | JAMAL | 5 | Crawford who won the 2014 Sixth Man of the Year Award |