| 100% | HGWELLS | 7 | "The Time Machine" author whose image appears on the "Sgt. Pepper" cover: 3 wds. |
| 77% | WCFIELDS | 8 | "My Little Chickadee" actor whose image appears on the "Sgt. Pepper" cover: 3 wds. |
| 67% | MAEWEST | 7 | "I'm No Angel" actress whose image appears on the "Sgt. Pepper" cover: 2 wds. |
| 61% | BOBDYLAN | 8 | "Blowin' in the Wind" singer whose image appears on the cover of the Beatles' "Sgt. Pepper's Lonely Hearts Club Band" album: 2 wds. |
| 46% | ALEXISSMITH | 11 | Singer/actress who appeared on the May 3, 1971, cover of Time Magazine with the headline "That Old Magic Relights Broadway" (2 wds.) |
| 43% | HGWELLS | 7 | "The Time Machine" author: 3 wds. |
| 41% | AREYOUTHERE | 11 | American sitcom "___, Chelsea?" in which Laura Prepon plays the author whose book the drama was based on: 3 wds. |
| 41% | MAYAANGELOU | 11 | "I Know Why the Caged Bird Sings," 18-Across, and 31-Across writer whose image appears on the first coin in the American Women Quarters series (2 wds.) |
| 39% | JAMESTAYLOR | 11 | Singer/songwriter who appeared on the March 1, 1971, cover of Time Magazine with the headline "The New Rock: Bittersweet and Low" (2 wds.) |
| 39% | BEVERLYSILLS | 12 | Singer/songwriter who appeared on the November 22, 1971, cover of Time Magazine with the corner banner "America's Queen of Opera" (2 wds.) |
| 38% | THELONIOUSMONK | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 28, 1964 (2 wds.) |
| 38% | WYNTONMARSALIS | 14 | Jazz legend who appeared on the cover of "Time" magazine on October 22, 1990 (2 wds.) |
| 37% | JACKDEMPSEY | 11 | First athlete to appear on the cover of Time magazine |
| 37% | SAHL | 4 | Comedian who appeared on the cover of Time, 8/15/1960 |
| 37% | SAHL | 4 | First-ever comedian to appear on the cover of Time (1960) |
| 37% | LANDON | 6 | Michael who appeared on the cover of TV Guide 22 times |
| 37% | JOHNLENNON | 10 | Former Beatle who appeared on the first cover of Rolling Stone (1967) (2 wds.) |
| 37% | MARKMCGWIRE | 11 | Slugger who appeared on the March 23, 1998, cover of Sports Illustrated (2 wds.) |
| 36% | ELLIOT | 6 | Page who became the first openly trans man to appear on the cover of Time magazine (2021) |
| 36% | KATVOND | 7 | Celebrity tattoo artist who appeared on the TV show "LA Ink": 3 wds. |
| 36% | NAOMAMPBELL | 11 | *Woman who was the first Black model to appear on the cover of Time |
| 36% | GIGI | 4 | Model Hadid who has appeared on the cover of "Vogue" more than 30 times |
| 35% | LAUREN | 6 | With 33-Across, "American Gigolo" actress who appeared on the cover of Vogue 28 times |
| 35% | WELLS | 5 | The Time Machine author |
| 35% | POE | 3 | Writer next to Jung on the ''Sgt. Pepper'' cover |
| 35% | TUBMAN | 6 | Harriet whose image is scheduled to appear on the twenty-dollar bill |
| 34% | MARYANNEEVANS | 13 | Author of "The Mill on the Floss" who wrote under the pen name George Eliot: 3 wds. |
| 34% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 34% | LOUISARMSTRONG | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 21, 1949, the first of only five jazz musicians to do so (2 wds.) |
| 34% | TONESANDI | 9 | Australian singer whose "Dance Monkey" was the #2 song on Spotify in 2020: 3 wds. |