| 100% | MARKMCGWIRE | 11 | Slugger who appeared on the March 23, 1998, cover of Sports Illustrated (2 wds.) |
| 73% | MARKMCGWIRE | 11 | Slugger on the cover of Sports Illustrated's March 23, 1998, issue (2 wds.) |
| 53% | 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.) |
| 50% | JOHNLENNON | 10 | Former Beatle who appeared on the first cover of Rolling Stone (1967) (2 wds.) |
| 50% | ELLEMACPHERSON | 14 | Australian model who's been on the cover of the Sports Illustrated Swimsuit Issue five times: 2 wds. |
| 49% | ELLE | 4 | Supermodel Macpherson who appeared five times on the cover of the Sports Illustrated Swimsuit Issue |
| 49% | KATEUPTON | 9 | Sports Illustrated Swimsuit Issue cover model who's #8 on the 2013 Maxim Hot 100 List: 2 wds. |
| 49% | THELONIOUSMONK | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 28, 1964 (2 wds.) |
| 49% | WYNTONMARSALIS | 14 | Jazz legend who appeared on the cover of "Time" magazine on October 22, 1990 (2 wds.) |
| 48% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 48% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 47% | KATEUPTON | 9 | "The Other Woman" actress who's been on the cover of the Sports Illustrated Swimsuit Issue four times: 2 wds. |
| 46% | 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.) |
| 45% | 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.) |
| 45% | 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.) |
| 45% | 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.) |
| 45% | TYRABANKS | 9 | "America's Next Top Model" creator who's been on the cover of the Sports Illustrated Swimsuit Issue three times: 2 wds. |
| 44% | PELE | 4 | Legendary athlete on the 6/23/75 cover of Sports Illustrated |
| 42% | TOMARNOLD | 9 | Comedian who appeared on "The Best Damn Sports Show Period" in the 2000s (2 wds.) |
| 41% | SAHL | 4 | Comedian who appeared on the cover of Time, 8/15/1960 |
| 41% | LANDON | 6 | Michael who appeared on the cover of TV Guide 22 times |
| 41% | SNOOKI | 6 | Reality TV star who appeared on the cover of Rolling Stone |
| 41% | FRANKDEFORD | 11 | Former Sports Illustrated writer who was Sportswriter of the Year six times (2 wds.) |
| 41% | ANNEHATHAWAY | 12 | "Interstellar" actress who appears in one of the stories on 27-Across (2 wds.) |
| 40% | DREWBREES | 9 | Quarterback who was Sports Illustrated's 2010 Sportsman of the Year: 2 wds. |
| 39% | LAUREN | 6 | With 33-Across, "American Gigolo" actress who appeared on the cover of Vogue 28 times |
| 39% | JOHNSLATTERY | 12 | "Mad Men" actor who appears in one of the stories on 27-Across (2 wds.) |
| 39% | ERINANDREWS | 11 | Female sportscaster who appeared on "Dancing With the Stars": 2 wds. |
| 39% | CHRISSYTEIGEN | 13 | Former Sports Illustrated Swimsuit model who was the #3 highest-earning model of 2018 (2 wds.) |
| 39% | GIGIHADID | 9 | Supermodel with 35 appearances on the cover of "Vogue" who co-hosts 32-Across (2 wds.) |