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.

Onstage, Mr. Raftery channels Ms. Wintour’s reputation for withering questions. “Are you wearing white socks with black shoes?” he asks the piano player.Credit…Justin J Wee for The New York Times