| 100% | TATUM | 5 | Art ___, jazz pianist who covered "Over the Rainbow" four times, in 1939, 1948, 1953, and 1956 |
| 33% | CASSIDY | 7 | Eva ___, singer who covered "Over the Rainbow" in 1992 |
| 32% | BEN | 3 | Golfer Hogan who won the U.S. Open four times between 1948 and 1953 |
| 31% | DUKE | 4 | ___ Ellington, pianist who collaborated on more than 1000 compositions and is considered one of the most influential figures in jazz |
| 31% | SECRETARIAT | 11 | 95-Across who made the covers of Time, Newsweek and Sports Illustrated in the same week |
| 31% | TATUM | 5 | Art —, US jazz pianist known for his improvisation who died in 1956 |
| 29% | SHEARING | 8 | George —, British jazz pianist and composer who died in 2011 |
| 29% | MONK | 4 | Thelonious —, US jazz pianist and composer who died in 1982 |
| 29% | STATELINES | 10 | Borders represented four times in this puzzle — both in the grid and on a map |
| 28% | EVANS | 5 | Gil —, Toronto-born jazz pianist and composer who died in 1988 |
| 28% | ISRAEL | 6 | ___ Kamakawiwo'ole, "Somewhere Over the Rainbow/What a Wonderful World" singer who was born in Hawaii |
| 27% | ETTA | 4 | Jazz singer ___ James who's in the Rock and Roll Hall of Fame |
| 27% | THAD | 4 | Jazz trumpeter Jones who played in and later led the Count Basie Orchestra |
| 26% | SCOTTJOPLIN | 11 | US pianist and composer associated with the ragtime style who died in 1917 |
| 26% | DEREK | 5 | John —, actor and director who played Joshua in 1956 film The Ten Commandments |
| 26% | OBAMA | 5 | Barack who was Time's Person of the Year in 2008 and 2012 |
| 26% | ARIANA | 6 | ___ Grande, singer who covered "Over the Rainbow" at a 2017 benefit concert |
| 25% | XXXXXXXXXX | 10 | Jazz pianist who played in Miles Davis's band |
| 25% | HOGAN | 5 | Golfer who won the British Open in 1953, the only time he ever competed in it |
| 25% | LUKE | 4 | ___ Kuechly, football linebacker who retired in 2020 and made it to the Pro Bowl seven times |
| 25% | BARACKOBAMA | 11 | Political victor who was Time's Person of the Year in 2008 and 2012: 2 wds. |
| 25% | NOR | 3 | Word appearing four times in the Fifth Amendment |
| 25% | FERRELL | 7 | Comic actor who plays jazz flute in "Anchorman" and stars in the new movie "Eurovision Song Contest" |
| 25% | MARSHAL | 7 | ___ Yanda, football guard who retired in 2020 and has made it to the Pro Bowl eight times |
| 25% | MASSINE | 7 | Leonide ---, Russian ballet dancer and choreographer who played Grischa Ljubov in 1948 film drama The Red Shoes |
| 25% | TONIMORRISON | 12 | "Beloved" author who received the American Academy of Arts and Letters Gold Medal in 2019: 2 wds. |
| 25% | ELDOCTOROW | 10 | "Ragtime" author who received the American Academy of Arts and Letters Gold Medal in 2013: 3 wds. |
| 25% | BEVERLYSILLS | 12 | Opera singer who chaired Lincoln Center and received the National Medal of Arts in 1990: 2 wds. |
| 25% | THEGUARDIANS | 12 | Persecuted and endangered journalists who were Time Magazine's Persons of the Year in 2018 (2 wds.) |
| 25% | JAMAL | 5 | Journalist Khashoggi who was on the cover of Time in 2018 |