| 100% | JOHNLENNON | 10 | Former Beatle who appeared on the first cover of Rolling Stone (1967) (2 wds.) |
| 61% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 58% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 57% | 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.) |
| 54% | SNOOKI | 6 | Reality TV star who appeared on the cover of Rolling Stone |
| 51% | 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.) |
| 50% | MARKMCGWIRE | 11 | Slugger who appeared on the March 23, 1998, cover of Sports Illustrated (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.) |
| 49% | MICHELLEOBAMA | 13 | Former First Lady and "Becoming" author who was on the cover of the Winter 2021/22 issue of Vogue Knitting: 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.) |
| 46% | 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.) |
| 46% | 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.) |
| 46% | RINGOSTARR | 10 | The Beatles drummer who is #14 on Rolling Stone's 100 Greatest Drummers of All Time (2 wds.) |
| 45% | CHADOCHOCINCO | 13 | Former name of an NFL player who appeared on "Dancing With the Stars" in 2010: 2 wds. |
| 43% | WARRENSAPP | 10 | Former NFL player who appeared on "Dancing With the Stars" in 2008: 2 wds. |
| 43% | NAOMICAMPBELL | 13 | British supermodel who was the first Black model on the cover of Vogue France: 2 wds. |
| 42% | KEITHRICHARDS | 13 | Rolling Stones guitarist who played a pirate in the third and fourth "Pirates of the Caribbean" films: 2 wds. |
| 42% | MICKJAGGER | 10 | Lead singer of the Rolling Stones who turned 77 on July 26, 2020 (2 wds.) |
| 41% | KEITHMOON | 9 | English drummer rated second-greatest drummer by Rolling Stone who was part of the band "The Who": 2 wds. |
| 41% | MICHAELSAM | 10 | Former NFL draft pick who appeared on "Dancing With the Stars" in 2015: 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% | ANNEHATHAWAY | 12 | "Interstellar" actress who appears in one of the stories on 27-Across (2 wds.) |
| 41% | MOSS | 4 | Actress Elisabeth who's been on the cover of Rolling Stone, ironically |
| 41% | MALIAOBAMA | 10 | Former First Daughter born on the Fourth of July, 1998: 2 wds. |
| 40% | 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. |
| 40% | MIA | 3 | Actress Farrow who was on the first cover of People magazine in 1974 |
| 40% | RUN | 3 | ___-D.M.C., the first rap group to appear on the cover of Rolling Stone |
| 40% | LUISTIANT | 9 | Former 27-Across pitcher who appeared as a guest star on the "Now Pitching, Sam Malone" episode of "Cheers" (2 wds.) |