In November 1992, actor Richard Gere became the first man to appear on the cover of the American fashion bible -- posing beside his supermodel wife at the time, Cindy Crawford.
It took another eight years for a guy to break through. This time it was George Clooney, who appeared with supermodel Gisele Bündchen in June 2000.
The NBA superstar also appeared with Gisele Bündchen on an April 2008 cover that generated a lot of criticism that James' pose and expression evoked Beauty and the Beast stereotypes.
The U.S. swimmer sandwiched himself between fellow Olympians Hope Solo and Serena Williams for a June 2012 cover ahead of the Summer Games in London -- for what would become the magazine's worst-selling cover of that year.
Editor Anna Wintour faced pushback for her March 2014 cover choice of Kanye West and Kim Kardashian -- whom the magazine dubbed "#worldsmosttalkedaboutcouple."
The actor-director teamed with his "Zoolander 2" co-star Penélope Cruz to promote the comedy (which was a box office dud) -- complete with a classic "Blue Steel" pose.
Ahead of the 2016 Olympics in Rio de Janeiro, U.S. decathlete Ashton Eaton posed beside model Gigi Hadid for the August 2016 issue
One year later, Gigi Hadid returned for the August 2017 cover -- this time posing with boyfriend Zayn Malik, the former One Direction singer whom she met shooting the video for his 2016 solo single "Pillowtalk."
The pop singer posed with his wife, Hailey Baldwin, on the March 2019 cover.
In December 2020, the former boy-band singer became the first man to grace the cover of Vogue solo.