Sexy & Musical! Every ‘People’s Sexiest Man Alive’ Who Has Hit the Billboard Hot 100

Jonathan Bailey joined an exclusive club on Monday (Nov. 3) when he was named People Magazine’s Sexiest Man Alive. But he also joins an even more exclusive club, as just the eighth Sexiest Man Alive who has also made the Billboard Hot 100.

Bailey cracked the Hot 100 in December 2024 with “Dancing Through Life” from Wicked. The track, featuring Ariana Grande, Ethan Slater, Marissa Bode and Cynthia Erivo, reached No. 90. Grande and Erivo went on to receive Oscar nominations for their roles, but Bailey was passed over for a nod.

Bailey’s selection was announced on The Tonight Show Starring Jimmy Fallon. The People cover line reads: “Wicked-ly handsome and oh-so-charming. We know, we nailed it.”

We went back through the 40-year history of People’s Sexiest Man Alive franchise and found seven previous title-holders who have made the Hot 100. In addition, six Sexiest Man Alive veterans starred in films that spawned Billboard 200-topping soundtracks. (Three of them also had Hot 100 hits, so we’ll save those mentions for the list below.)

Sean Connery, who was deemed Sexiest in 1989, starred in seven James Bond films, including Goldfinger, with a soundtrack that logged three weeks at No. 1 in 1965. (Here’s some sexy trivia for you: Connery was 59 when he took the title, making him the oldest Sexiest Man Alive in the franchise’s history.)

Tom Cruise, People’s choice for 1990, starred in Top Gun, with a soundtrack that logged five weeks at No. 1 in 1986. It also spawned the Oscar-winning smash “Take My Breath Away,” a Hot 100-topping hit for Berlin.

George Clooney, the choice for 1997, starred in O Brother, Where Art Thou?, with a soundtrack that logged two weeks at No. 1 in 2002. It also won album of the year at that year’s Grammys. Clooney has an even stronger connection to music: His aunt was Rosemary Clooney, one of the top pop singers of the 1950s — and a top jazz singer for decades.

Here they are, the hunks who can sing, too — all the men who have been named People’s Sexiest Man Alive who have also made the Hot 100.