Anna Wintour Sings! (Sort Of.)

In his main job, Ryan Raftery works in the New York offices of LVMH, doing talent recruitment.

In his second, he croons and twerks at Joe’s Pub, the Public Theater’s downtown nightspot, while starring in three different musicals about three famous women: Anna Wintour, the longtime editor of Vogue; Kris Jenner, the Machiavellian matriarch of the world’s best known reality show clan; and Martha Stewart, a domestic diva known both for her popovers and her 2004-5 prison stint.

Call it “Torch Song Trilogy, Media Divas Edition.”

“I’m like Persephone,” Mr. Raftery said on a recent evening after a performance as Ms. Wintour. “Once or twice a year, I get to come up from the deep and be a star.”

Onstage, he wore stiletto boots, an emerald green dress bought on Amazon for $39, and a tan, belted Alberta Ferretti coat. Later, seated in his dressing room, he wore a button-down shirt from Scotch & Soda, jeans and a baseball cap.

Pumas were on his feet. In his hand was his chosen cocktail, vodka with orange juice and a splash of cranberry.

According to Mr. Raftery, the common denominator among his subjects is a relentless need for relevance.

He referred to a favorite quote from Carrie Fisher: “Celebrity is just obscurity biding its time.” “These three women have very different ideas about what relevancy means, but it’s integral to all of their lives,” he added.

The songs in the three shows, which run through Thursday, use existing pop hits, with lyrics rewritten by Mr. Raftery. The plotlines are phantasmagorical but draw inspiration from the subjects’ biographies.

For example, in “Ryan Raftery Is the Most Powerful Woman in Fashion,” the show about Ms. Wintour, he performs “Drunk at Vogue,” a takeoff of Beyoncé’s “Drunk in Love.”

Granted, Mr. Raftery has never heard that Ms. Wintour drinks much of anything at Vogue besides Starbucks, which, sipped from a Venti cup and in her hands most of the time, has become its own accessory. (Mr. Raftery uses one as a prop.)

But by adding alcohol to the mix and having Ms. Wintour bounce her booty in her office with the door shut, Mr. Raftery creates an emotional struggle out of Ms. Wintour’s reputation for being controlling and achieves a sense of camp theater. (Mid-number, Mr. Raftery pauses the proceedings to deliver an admonishment to his piano player: “Are you wearing white socks with black shoes?”)

Mr. Raftery, 46, grew up in Brooklyn. His father, a firefighter, died from lung cancer when Mr. Raftery was 12. His mother worked in New York Newsday’s circulation department.

After attending James Madison High School, whose graduates include Senator Bernie Sanders and Ruth Bader Ginsburg, Mr. Raftery went to New York University’s Tisch School of the Arts, where, in 1999, he received a bachelor’s degree in drama.

Afterward, Mr. Raftery acted on television shows such as “Law & Order: Special Victims Unit” (he played an Amish teenager with measles) and “Malcolm in the Middle.”

He sang and danced but could not get cast on Broadway. He staged one-man shows about himself that were largely ignored.

Eventually, Mr. Raftery started writing shows about other people, the first of whom was Ms. Wintour.

When the show about her became a hit at Joe’s Pub in 2014, he created others, using as inspiration the Bravo executive Andy Cohen, the designer Calvin Klein, the former first daughter Ivanka Trump, the artist Andy Warhol and, finally, Ms. Jenner.

Never mind that he had not watched “Keeping Up With the Kardashians.”

“They’re actually not that interesting,” Mr. Raftery said.

So he came up with a gonzo plotline in which Ms. Jenner flies to Laos for fertility treatments, changes her mind about wanting another baby and then, in the aftermath of the repeal of Roe v. Wade, reinvents herself as an abortion rights activist. (Also: At some point, she gets amnesia.)

None of Mr. Raftery’s subjects have come to see him perform, although Ms. Stewart sent a number of people from her staff, he said.

Ms. Wintour’s daughter, Bee Carrozzini, also came to Joe’s Pub for a viewing, then stopped backstage.

“We took a picture,” said Mr. Raftery.

He has long wanted to play Mariah Carey. “But I’m white, and I think her biraciality makes that impossible.”

He would also like to stretch past the milieu of divas and gay men.

“It would be fun to play Roger Ailes, though I’m not sure he’d be a hit with my fan base,” he said. “Why? Who do you think I should play next?”