| 100% | SAHL | 4 | First-ever comedian to appear on the cover of Time (1960) |
| 76% | JACKDEMPSEY | 11 | First athlete to appear on the cover of Time magazine |
| 72% | SAHL | 4 | Comedian who appeared on the cover of Time, 8/15/1960 |
| 71% | NAOMAMPBELL | 11 | *Woman who was the first Black model to appear on the cover of Time |
| 67% | NAOMAMPBELL | 11 | First Black model to appear on the cover of French Vogue |
| 65% | ELLIOT | 6 | Page who became the first openly trans man to appear on the cover of Time magazine (2021) |
| 63% | 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.) |
| 60% | POSESFOR | 8 | Sits to appear on the cover of, say |
| 56% | LANDON | 6 | Michael who appeared on the cover of TV Guide 22 times |
| 56% | RUN | 3 | ___-D.M.C., the first rap group to appear on the cover of Rolling Stone |
| 55% | GIGI | 4 | Model Hadid who has appeared on the cover of "Vogue" more than 30 times |
| 55% | ADELE | 5 | First person to appear simultaneously on the American and British covers of Vogue (Oct. 2021) |
| 55% | LAUREN | 6 | With 33-Across, "American Gigolo" actress who appeared on the cover of Vogue 28 times |
| 53% | RETTON | 6 | First woman to appear on the front of a Wheaties box |
| 53% | SAHL | 4 | Canadian-born comedian once featured on the cover of Time |
| 51% | THELONIOUSMONK | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 28, 1964 (2 wds.) |
| 51% | WYNTONMARSALIS | 14 | Jazz legend who appeared on the cover of "Time" magazine on October 22, 1990 (2 wds.) |
| 51% | JOHNLENNON | 10 | Former Beatle who appeared on the first cover of Rolling Stone (1967) (2 wds.) |
| 49% | OTT | 3 | Giant on the cover of Time magazine, 1945 |
| 48% | LADYDI | 6 | She was on the cover of back-to-back issues of Time in September 1997 |
| 48% | JAMAL | 5 | Journalist Khashoggi who was on the cover of Time in 2018 |
| 48% | SNOOKI | 6 | Reality TV star who appeared on the cover of Rolling Stone |
| 47% | DALI | 4 | 32-year-old artist pictured on the cover of Time magazine in 1936 |
| 47% | ERNEST | 6 | Name on the cover of ''A Farewell to Arms'' |
| 47% | ANNEMEARA | 9 | Spouse on the cover of ''Married to Laughter'' (2001) |
| 47% | MEARA | 5 | Wife on the cover of ''Married to Laughter'' (2001) |
| 47% | STAN | 4 | Name on the cover of ''How to Draw Superheroes'' |
| 47% | LUCILLEBALL | 11 | Star who appeared on the first cover of TV Guide (and who holds the record for the most TV Guide covers) (2 wds.) |
| 47% | 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.) |
| 46% | PEOPLEMAGAZINE | 14 | Mia Farrow was on the cover of its first issue |