| 100% | BENSTILLER | 10 | Male "Zoolander" star featured on the cover of Vogue in February 2016: 2 wds. |
| 73% | GEORGECLOONEY | 13 | Male "Up in the Air" star featured on the cover of Vogue in June 2000: 2 wds. |
| 67% | RYANLOCHTE | 10 | Male Olympic swimming medalist featured on the cover of Vogue in June 2012: 2 wds. |
| 44% | MARTHASTEWART | 13 | Entrepreneur and lifestyle guru who was on the cover of the Holiday 2011 issue of Vogue Knitting: 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% | MICHELLEOBAMA | 13 | Former First Lady and "Becoming" author who was on the cover of the Winter 2021/22 issue of Vogue Knitting: 2 wds. |
| 42% | THELONIOUSMONK | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 28, 1964 (2 wds.) |
| 42% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 41% | GERE | 4 | First man featured on the cover of the U.S. edition of Vogue |
| 41% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 40% | NAOMICAMPBELL | 13 | British supermodel who was the first Black model on the cover of Vogue France: 2 wds. |
| 40% | GIGIHADID | 9 | Supermodel with 35 appearances on the cover of "Vogue" who co-hosts 32-Across (2 wds.) |
| 38% | 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.) |
| 38% | ELLEMACPHERSON | 14 | Australian model who's been on the cover of the Sports Illustrated Swimsuit Issue five times: 2 wds. |
| 38% | MADDENNFL | 9 | Video game franchise that featured 15-Across on the cover of the 2011 version: 2 wds. |
| 37% | ALICIAKEYS | 10 | "No One" singer featured on the 2009 Jay Z hit "Empire State of Mind": 2 wds. |
| 37% | WARMBODIES | 10 | Film released in February 2013 starring Nicholas Hoult that features walking corpses: 2 wds. |
| 37% | MARKMCGWIRE | 11 | Slugger on the cover of Sports Illustrated's March 23, 1998, issue (2 wds.) |
| 37% | ZEBRACROSSING | 13 | Prominent feature of the street on the cover of 48-Across (2 wds.) |
| 37% | MARKRYLANCE | 11 | "Bridge of Spies" star featured in the 2017 WWII film "Dunkirk": 2 wds. |
| 37% | TYRABANKS | 9 | "America's Next Top Model" creator who's been on the cover of the Sports Illustrated Swimsuit Issue three times: 2 wds. |
| 36% | ALA | 3 | In the style of, on a menu: 2 wds. |
| 36% | ALA | 3 | In the manner of, on a menu: 2 wds. |
| 36% | ASTO | 4 | On the topic of, in memos (2 wds.) |
| 36% | MIRANDALAMBERT | 14 | "Vice" singer who came in third on the first season of "Nashville Star": 2 wds. |
| 36% | AMERICANWOMAN | 13 | Lenny Kravitz's cover song which featured on the soundtrack of the 1999 film "Austin Powers: The Spy Who Shagged Me": 2 wds. |
| 36% | SAHL | 4 | Canadian-born comedian once featured on the cover of Time |
| 36% | PRECIOUSLEE | 11 | Model on the cover of Vogue's 2021 September issue |
| 36% | GERE | 4 | Richard who was the first man featured on the cover of American Vogue |
| 36% | GRITTY | 6 | Mascot turned meme who was featured on the cover of Artforum |