| 100% | 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.) |
| 62% | 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.) |
| 58% | 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.) |
| 41% | LAUREN | 6 | With 33-Across, "American Gigolo" actress who appeared on the cover of Vogue 28 times |
| 39% | THELONIOUSMONK | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 28, 1964 (2 wds.) |
| 39% | WYNTONMARSALIS | 14 | Jazz legend who appeared on the cover of "Time" magazine on October 22, 1990 (2 wds.) |
| 37% | 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.) |
| 37% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 36% | KATEUPTON | 9 | "The Other Woman" actress who's been on the cover of the Sports Illustrated Swimsuit Issue four times: 2 wds. |
| 36% | BRETMICHAELS | 12 | Rock singer with Poison who finished seventh on season 3 of "The Masked Singer" as the Banana: 2 wds. |
| 36% | MICHELLEBRANCH | 14 | The Wreckers singer who appeared on "The Big Interview with Dan Rather" with her husband, Patrick Carney of the Black Keys (2 wds.) |
| 36% | JESSEMCCARTNEY | 14 | Pop singer with Dream Street who was the runner-up on season 3 of "The Masked Singer" as the Turtle: 2 wds. |
| 34% | MARKMCGWIRE | 11 | Slugger who appeared on the March 23, 1998, cover of Sports Illustrated (2 wds.) |
| 34% | KRYSTENRITTER | 13 | "Jessica Jones" actress who was on the cover of the Late Winter 2018 issue of Vogue Knitting: 2 wds. |
| 34% | SUE | 3 | WNBA great Bird who appeared with Megan Rapinoe on the cover of ESPN The Magazine's Body Issue in 2018 |
| 34% | TORISPELLING | 12 | Actress who was the Unicorn on season 1 of "The Masked Singer": 2 wds. |
| 34% | CINDYCRAWFORD | 13 | American supermodel with a beauty mark who appeared on more than 1,000 magazine covers: 2 wds. |
| 34% | ELLIOT | 6 | Page who became the first openly trans man to appear on the cover of Time magazine (2021) |
| 34% | CHADOCHOCINCO | 13 | Former name of an NFL player who appeared on "Dancing With the Stars" in 2010: 2 wds. |
| 33% | JANETJACKSON | 12 | Actress and singer who played the Evans family's neighbor Penny on "Good Times": 2 wds. |
| 33% | JOHNLENNON | 10 | Former Beatle who appeared on the first cover of Rolling Stone (1967) (2 wds.) |
| 33% | 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. |
| 33% | LANDON | 6 | Michael who appeared on the cover of TV Guide 22 times |
| 33% | ANNAKENDRICK | 12 | Actress of "Up in the Air" who rose to prominence with 1998 Broadway musical "High Society": 2 wds. |
| 33% | 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.) |
| 33% | MEMORYLANE | 10 | Old Dominion No. 4 country single with the lyrics "Yeah, I might as well live there, baby / That's where I spend most of my time" (2 wds.) |
| 33% | DIONNEWARWICK | 13 | "Walk On By" singer who was the Mouse on season 3 of "The Masked Singer": 2 wds. |
| 32% | ELLEMACPHERSON | 14 | Australian model who's been on the cover of the Sports Illustrated Swimsuit Issue five times: 2 wds. |
| 32% | CAROLCHANNING | 13 | Singer/actress who headlined the original production of "Hello, Dolly!" in 1964: 2 wds. |
| 32% | ANNEHATHAWAY | 12 | "Interstellar" actress who appears in one of the stories on 27-Across (2 wds.) |