| 100% | POSESFOR | 8 | Sits to appear on the cover of, say |
| 71% | JACKDEMPSEY | 11 | First athlete to appear on the cover of Time magazine |
| 70% | SAHL | 4 | First-ever comedian to appear on the cover of Time (1960) |
| 70% | NAOMAMPBELL | 11 | First Black model to appear on the cover of French Vogue |
| 59% | 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.) |
| 58% | NAOMAMPBELL | 11 | *Woman who was the first Black model to appear on the cover of Time |
| 58% | ADELE | 5 | First person to appear simultaneously on the American and British covers of Vogue (Oct. 2021) |
| 58% | SAHL | 4 | Comedian who appeared on the cover of Time, 8/15/1960 |
| 58% | LANDON | 6 | Michael who appeared on the cover of TV Guide 22 times |
| 58% | SNOOKI | 6 | Reality TV star who appeared on the cover of Rolling Stone |
| 56% | ERNEST | 6 | Name on the cover of ''A Farewell to Arms'' |
| 56% | ANNEMEARA | 9 | Spouse on the cover of ''Married to Laughter'' (2001) |
| 56% | MEARA | 5 | Wife on the cover of ''Married to Laughter'' (2001) |
| 56% | STAN | 4 | Name on the cover of ''How to Draw Superheroes'' |
| 56% | GIGI | 4 | Model Hadid who has appeared on the cover of "Vogue" more than 30 times |
| 56% | ELLIOT | 6 | Page who became the first openly trans man to appear on the cover of Time magazine (2021) |
| 55% | LAUREN | 6 | With 33-Across, "American Gigolo" actress who appeared on the cover of Vogue 28 times |
| 55% | THELONIOUSMONK | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 28, 1964 (2 wds.) |
| 55% | WYNTONMARSALIS | 14 | Jazz legend who appeared on the cover of "Time" magazine on October 22, 1990 (2 wds.) |
| 54% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 53% | RUN | 3 | ___-D.M.C., the first rap group to appear on the cover of Rolling Stone |
| 53% | AFRO | 4 | Hairstyle on the cover of the Notorious B.I.G.'s Ready to Die |
| 53% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 53% | PANIC | 5 | DON'T ___ (phrase on the cover of the novel "Hitchhiker's Guide to the Galaxy") |
| 52% | RETTON | 6 | First woman to appear on the front of a Wheaties box |
| 52% | STEAM | 5 | ___ Locomotive, train featured on the cover of the packaging for the board game "Ticket to Ride" |
| 51% | KENNY | 5 | London-born singer-songwriter and actor who appears on the cover of 1973 album Band on the Run by Paul McCartney and Wings |
| 51% | JOHNLENNON | 10 | Former Beatle who appeared on the first cover of Rolling Stone (1967) (2 wds.) |
| 51% | MARKMCGWIRE | 11 | Slugger who appeared on the March 23, 1998, cover of Sports Illustrated (2 wds.) |