| 100% | GEORGECLOONEY | 13 | Male "Up in the Air" star featured on the cover of Vogue in June 2000: 2 wds. |
| 76% | BENSTILLER | 10 | Male "Zoolander" star featured on the cover of Vogue in February 2016: 2 wds. |
| 76% | RYANLOCHTE | 10 | Male Olympic swimming medalist featured on the cover of Vogue in June 2012: 2 wds. |
| 46% | NAOMICAMPBELL | 13 | British supermodel who was the first Black model on the cover of Vogue France: 2 wds. |
| 45% | MADDENNFL | 9 | Video game franchise that featured 15-Across on the cover of the 2011 version: 2 wds. |
| 44% | MARKRYLANCE | 11 | "Bridge of Spies" star featured in the 2017 WWII film "Dunkirk": 2 wds. |
| 44% | NAOMICAMPBELL | 13 | "American Horror Story: Hotel" actress who was the first black model on the cover of French Vogue : 2 wds. |
| 42% | GEORGECLOONEY | 13 | "Up in the Air" star who cofounded the Casamigos tequila company: 2 wds. |
| 42% | MARTHASTEWART | 13 | Entrepreneur and lifestyle guru who was on the cover of the Holiday 2011 issue of Vogue Knitting: 2 wds. |
| 42% | KRYSTENRITTER | 13 | "Jessica Jones" actress who was on the cover of the Late Winter 2018 issue of Vogue Knitting: 2 wds. |
| 42% | ZEBRACROSSING | 13 | Prominent feature of the street on the cover of 48-Across (2 wds.) |
| 41% | GEORGECLOONEY | 13 | American actor from "Up in the Air" who is a former UN messenger of peace and is a part of the "Not on Our Watch" organization: 2 wds. |
| 41% | GERE | 4 | Richard who was the first man featured on the cover of American Vogue |
| 41% | MICHELLEOBAMA | 13 | Former First Lady and "Becoming" author who was on the cover of the Winter 2021/22 issue of Vogue Knitting: 2 wds. |
| 41% | BRUCEJENNER | 11 | Former name of the Olympic decathlon gold medalist featured on Wheaties boxes in 1977 and 2012: 2 wds. |
| 41% | TERRELLOWENS | 12 | Hall of Fame wide receiver who competed on "Dancing With the Stars" in 2017: 2 wds. |
| 41% | 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. |
| 41% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 41% | CHADOCHOCINCO | 13 | Former name of an NFL player who appeared on "Dancing With the Stars" in 2010: 2 wds. |
| 40% | MIRANDALAMBERT | 14 | "Vice" singer who came in third on the first season of "Nashville Star": 2 wds. |
| 40% | GERE | 4 | First man featured on the cover of the U.S. edition of Vogue |
| 40% | DARIUSRUCKER | 12 | Hootie and the Blowfish lead singer who's getting a Recording star on the Hollywood Walk of Fame in 2024: 2 wds. |
| 39% | ANNAKENDRICK | 12 | Actress of "Up in the Air" who rose to prominence with 1998 Broadway musical "High Society": 2 wds. |
| 39% | MICHELLEYEOH | 12 | "Everything Everywhere All at Once" actress who's getting a Motion Pictures star on the Hollywood Walk of Fame in 2024: 2 wds. |
| 39% | BEAUTIFULMIND | 13 | 2001 American biographical drama film starring Russell Crowe, based on the life of a Nobel Laureate in Economics, Josh Nash, "A ___": 2 wds. |
| 39% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 39% | MINDYKALING | 11 | "The Office" actress who was honored with a star on the Hollywood Walk of Fame in 2023 (2 wds.) |
| 39% | BOBBYRYDELL | 11 | "Volare" singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 39% | GOODVIBRATIONS | 14 | Number-one hit released by The Beach Boys in 1966 which was featured in the climax scene of "Vanilla Sky" starring Tom Cruise: 2 wds. |
| 38% | GARRETTMORRIS | 13 | "2 Broke Girls" actor who was honored with a star on the Hollywood Walk of Fame in 2023 (2 wds.) |