| 100% | SAHL | 4 | Comedian who appeared on the cover of Time, 8/15/1960 |
| 66% | SAHL | 4 | First-ever comedian to appear on the cover of Time (1960) |
| 65% | LANDON | 6 | Michael who appeared on the cover of TV Guide 22 times |
| 64% | LAUREN | 6 | With 33-Across, "American Gigolo" actress who appeared on the cover of Vogue 28 times |
| 60% | THELONIOUSMONK | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 28, 1964 (2 wds.) |
| 60% | WYNTONMARSALIS | 14 | Jazz legend who appeared on the cover of "Time" magazine on October 22, 1990 (2 wds.) |
| 58% | JACKDEMPSEY | 11 | First athlete to appear on the cover of Time magazine |
| 57% | SNOOKI | 6 | Reality TV star who appeared on the cover of Rolling Stone |
| 57% | GIGI | 4 | Model Hadid who has appeared on the cover of "Vogue" more than 30 times |
| 56% | 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.) |
| 55% | TERESA | 6 | Mother who appeared on two covers of Time |
| 55% | 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.) |
| 55% | 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.) |
| 55% | 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.) |
| 54% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 53% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 52% | ELLIOT | 6 | Page who became the first openly trans man to appear on the cover of Time magazine (2021) |
| 52% | ELLE | 4 | Supermodel Macpherson who appeared five times on the cover of the Sports Illustrated Swimsuit Issue |
| 52% | JOHNLENNON | 10 | Former Beatle who appeared on the first cover of Rolling Stone (1967) (2 wds.) |
| 52% | AHAB | 4 | Obsessed sea captain who appeared on the final season of "Once Upon a Time" |
| 52% | 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% | SAHL | 4 | Canadian-born comedian once featured on the cover of Time |
| 51% | KENNYLYNCH | 10 | London-born singer-songwriter and actor who appears on the cover of 1973 record album Band on the Run by Paul McCartney and Wings |
| 48% | OTT | 3 | Giant on the cover of Time magazine, 1945 |
| 48% | 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% | NAOMAMPBELL | 11 | First Black model to appear on the cover of French Vogue |
| 46% | WALTERS | 7 | Barbara on the cover of 15 TV Guides |
| 46% | DALI | 4 | 32-year-old artist pictured on the cover of Time magazine in 1936 |
| 45% | TOMARNOLD | 9 | Comedian who appeared on "The Best Damn Sports Show Period" in the 2000s (2 wds.) |