| 100% | GIGIHADID | 9 | Supermodel with 35 appearances on the cover of "Vogue" who co-hosts 32-Across (2 wds.) |
| 46% | BENSTILLER | 10 | Male "Zoolander" star featured on the cover of Vogue in February 2016: 2 wds. |
| 45% | RYANLOCHTE | 10 | Male Olympic swimming medalist featured on the cover of Vogue in June 2012: 2 wds. |
| 44% | KRYSTENRITTER | 13 | "Jessica Jones" actress who was on the cover of the Late Winter 2018 issue of Vogue Knitting: 2 wds. |
| 43% | MARTHASTEWART | 13 | Entrepreneur and lifestyle guru who was on the cover of the Holiday 2011 issue of Vogue Knitting: 2 wds. |
| 43% | CAITLYNJENNER | 13 | TV personality making her first public appearance on the July cover of Vanity Fair: 2 wds. |
| 41% | SAMHEUGHAN | 10 | Scottish actor on "Outlander" who co-hosts 57-Across with 35-Across (2 wds.) |
| 41% | LAUREN | 6 | With 33-Across, "American Gigolo" actress who appeared on the cover of Vogue 28 times |
| 40% | MICHELLEOBAMA | 13 | Former First Lady and "Becoming" author who was on the cover of the Winter 2021/22 issue of Vogue Knitting: 2 wds. |
| 39% | NAOMICAMPBELL | 13 | "American Horror Story: Hotel" actress who was the first black model on the cover of French Vogue : 2 wds. |
| 38% | ELLEMACPHERSON | 14 | Australian model who's been on the cover of the Sports Illustrated Swimsuit Issue five times: 2 wds. |
| 38% | GEORGECLOONEY | 13 | Male "Up in the Air" star featured on the cover of Vogue in June 2000: 2 wds. |
| 38% | MADDENNFL | 9 | Video game franchise that featured 15-Across on the cover of the 2011 version: 2 wds. |
| 38% | ADAMLAMBERT | 11 | Runner-up on the eighth season of American Idol, who has collaborated with the British rock band "Queen" as lead vocalist: 2 wds. |
| 37% | AUDRAMCDONALD | 13 | Six-time Tony-winning actress who co-hosted the Tony Awards with 43-Across in 2021 (2 wds.) |
| 37% | THELONIOUSMONK | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 28, 1964 (2 wds.) |
| 37% | WYNTONMARSALIS | 14 | Jazz legend who appeared on the cover of "Time" magazine on October 22, 1990 (2 wds.) |
| 37% | 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.) |
| 37% | 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.) |
| 37% | 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.) |
| 37% | TANFRANCE | 9 | "Queer Eye" style expert who co-hosts 32-Across (2 wds.) |
| 37% | ALFONSORIBEIRO | 14 | "Dancing With the Stars" host who played one of Ricky's friends on 19-Across: 2 wds. |
| 36% | WARREN | 6 | With 35-Across, actor who played Clyde, one of the title characters on the run in 1967's "Bonnie and Clyde" |
| 36% | 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% | LESLIEODOMJR | 12 | "Hamilton" Tony winner who co-hosted the Tony Awards with 31-Across in 2021 (3 wds.) |
| 35% | HALEYBENNETT | 12 | "The Girl on the Train" actress who co-starred with Denzel Washington in "The Magnificent Seven" (2 wds.) |
| 35% | GRAHAMMCTAVISH | 14 | Scottish actor on "Outlander" who co-hosts 57-Across with 16-Across (2 wds.) |
| 35% | MARKMCGWIRE | 11 | Slugger who appeared on the March 23, 1998, cover of Sports Illustrated (2 wds.) |
| 35% | MARKMCGWIRE | 11 | Slugger on the cover of Sports Illustrated's March 23, 1998, issue (2 wds.) |