Sometimes even the most iconic pop culture figures can surprise you. RuPaul’s Drag Race season 8 winner Bob the Drag Queen recently revealed in a playful interview with Entertainment Weekly that he spent years assuming Paul Shaffer — the bald-headed band leader from Late Night with David Letterman and The Late Show — was gay.

The reason? Shaffer co-wrote one of the most beloved queer anthems of all time: the Weather Girls’ 1982 classic It’s Raining Men.

“I Thought He Was Gay for So Long”

While discussing his favorite LGBTQ pop culture moments, Bob singled out It’s Raining Men as a top-tier gay anthem.

“First of all, did you all know that Paul Shaffer wrote this song?” Bob asked in disbelief. “Yeah, the bald-headed guy from Letterman? Yeah, he wrote this song.”

Because of the song’s status in queer culture, Bob assumed Shaffer was part of the LGBTQ community.

“I thought he was gay for so long,” Bob said, laughing. “And then I met him recently, and he was like, ‘This is my wife!’”

Bob recalled his shock with a chuckle: “I said, ‘Oh!’ Well, you learn something new every day.”

Shaffer’s Longtime Marriage

Shaffer, now 75, has been married to Cathy Vasapoli since 1990, and the couple share two children. Despite decades of working in the public eye alongside David Letterman, Shaffer has largely kept his family life private — which only added to Bob’s initial misconception.

Performing Together

The story came full circle earlier this year when Bob actually got to perform It’s Raining Men live with Shaffer in Los Angeles.

The performance was part of the Let’s Get L.Aid benefit concert, which raised money for wildfire relief in Southern California. For Bob, the chance to belt the anthem alongside its composer was a career highlight.

Speaking about the song’s enduring legacy, Bob praised its campy brilliance: “The singing is so good, it’s so iconic.”

The Generational Test of “It’s Raining Men”

Bob also shared a tongue-in-cheek way to test a crowd’s age at a nightclub when the song plays.

“If you’re ever in a gay bar and you hear this song, look around,” he explained. “Every queer over 35 years old will do the clap. Every queer will do the clap [at one part in the song]. You know where it is.”

He joked, “That’s how you know someone is over 35 years old. And also the knee pain.”

Shaffer’s Place in Pop Culture

For many, Shaffer is remembered not only as a songwriter and producer but also as David Letterman’s trusted sidekick and musical director.

He joined Late Night with David Letterman in 1982, staying with the NBC show until 1993.

When Letterman jumped to CBS to launch The Late Show in 1993, Shaffer followed — leading the CBS Orchestra until Letterman’s retirement in 2015.

For over 30 years, Shaffer was a nightly television presence, his bald head, flashy suits, and quick comedic banter with Letterman becoming part of the show’s DNA.

While mainstream audiences mostly knew him as Letterman’s music man, Shaffer was always a respected musician in his own right, having worked with acts like Diana Ross, Yoko Ono, and the Blues Brothers band.

The Lasting Power of It’s Raining Men

Released in 1982 by the Weather Girls (Martha Wash and Izora Armstead), It’s Raining Men quickly became a disco and drag-floor staple. With its outrageous imagery, powerhouse vocals, and camp appeal, the track was embraced as a gay anthem almost immediately.

Co-written by Shaffer and Paul Jabara (who also co-wrote Last Dance for Donna Summer), the song represented the joyful, larger-than-life spirit of queer nightlife at the time.

Even four decades later, its chorus remains instantly recognizable — whether at Pride parades, drag shows, or pop culture references in films like Bridget Jones’s Diary and shows like RuPaul’s Drag Race.

Bob’s Role as Cultural Commentator

Bob the Drag Queen — also known as Caldwell Tidicue — has become more than just a Drag Race winner. In addition to touring as a comedian and drag performer, he co-hosts the Sibling Rivalry podcast with fellow drag star Monét X Change and co-stars in HBO’s We’re Here.

His knack for mixing comedy with cultural critique made his comments about Shaffer especially endearing: they highlighted how deeply music, television, and queer culture intersect.

For Bob, learning that Shaffer wasn’t gay didn’t diminish the anthem’s power — it just added a layer of humorous surprise.

The Bottom Line

Bob the Drag Queen’s playful revelation about assuming Paul Shaffer was gay for writing It’s Raining Men shows just how strongly certain songs and cultural moments become tied to queer identity.

While Shaffer may not have been part of the LGBTQ community, his contribution gave the world one of its most enduring anthems — and his long career alongside David Letterman cemented him as a cultural mainstay.

For Bob, the moment was less about embarrassment than delight: a reminder that pop culture is full of surprises, and that sometimes even our assumptions about icons come with a punchline.