Raven O, a Nightlife Fixture for Four Decades, Takes a Final Bow

For a stage artist who has made gender fluidity a cornerstone of his career, Raven O isn’t especially picky about pronouns. “When people ask,” he explained recently, “I say he or she, or both.” (“They” is out: “That just doesn’t make any sense to me.”)

Acquaintances often use the first, but while growing up in Oahu, Hawaii, he was frequently assumed to be female: “People would say to my mother, ‘What a beautiful girl.’” The truth was more complicated, he discovered. “In Hawaiian culture, there is the mahu — the two-spirit personality,” he said. “They’re the healers and teachers and spiritual guides, revered, but colonialism and white supremacy turned it into something bad. I thought it was an insult. Then I learned it was a great thing. I identify as mahu — he/she.”

Downing a large bottle of water on a brisk December afternoon, Raven O — he prefers to always be called by his full show-business moniker, which retains only the first letter of his given last name — exuded a relaxed charisma that defied all gender stereotypes. Turning up at the East Village alt-cabaret spot Pangea, where he has frequently performed, Raven O, 59, sported vinyl pants and a turtleneck sweater, both black, his naturally silver-white hair cascading down to his shoulders. His jacket was designed by the glam rocker Patrick Briggs, one of numerous collaborators and friends whose projects he would plug. An anarchy sign was stitched on one sleeve, the Japanese translation for a profane command on the other.

Neither adornment matched Raven O’s vibe, which was warm and wistful as he traversed a range of subjects, among them his apparently imminent retirement from live performance.

Since the ’80s, he has choreographed, directed, hosted, danced and sung — in a warmly dusky, rangy voice that eventually became his primary asset — in storied venues such as Boy Bar, the Box, Bar d’O and Joe’s Pub. After spending the Covid-19 shutdown in Hawaii with his husband, John Deutzman, a retired investigative television reporter whom he proudly called “a badass,” Raven O had hoped to resume appearances on a regular basis.

But Deutzman worried about his spouse’s increasing struggles with severe osteoarthritis — a condition that plagued Raven O’s father and grandfather and currently affects his older brother. An athlete and fitness trainer in his youth, he also suffers from spinal stenosis and bone spurs. “John said, ‘You can’t work. You can’t even walk,’” Raven O said. “I told him I could do this another 10 years, but coming back into the colder weather taught me that, no, I can’t.”

Three farewell shows are now scheduled before Raven O returns to Oahu, where he plans to begin stem cell therapy. He’ll appear at Pangea for two sets on Saturday; on Sunday, he’ll join fellow nightlife stalwarts Joey Arias and Sherry Vine at Indochine, for the latest and likely last anniversary of their Bar d’O collaborations in the ’90s, which fused bawdy and elegant drag — or “showing my female mahu side,” for Raven O — with soulful singing and spicy banter.

Arias, who worked with and championed Raven O for years before that decade-long stint, said Raven O’s last chapter is far from written. “I think Raven’s going to reinvent himself without even knowing it. The body may retire, but his mind won’t, or his love of music and art and dance and people,” Arias said. “I think his legacy is in being honest — not wasting time with trivial questions, being very direct, being able to shock people with his use of language.”

As a fledgling performer, Raven O had two roommates undergoing gender transitions, and considered following their lead. “We had a band called FDR Drive, and one day at rehearsals I realized I was standing to use the bathroom, and trans women don’t do that. I had a moment of clarity: I was doing this for the wrong reason — because I got more positive attention as a woman than as a male.”

One can expect similar candor in an upcoming memoir about Raven O’s New York adventures. “Kate Rigg, one of my hanai sisters, is writing it with me,” he said, using the Hawaiian term for friends essentially adopted as siblings; he has a bunch of them. Raven O arrived in New York at 18 and, by his account, spent most of the ’80s and early ’90s homeless.

“When it got cold, I’d find a place to sleep, usually by picking up a guy,” Raven O said, with a matter-of-fact smile. “I was a hooker, too; I sang for my supper, but if I needed money I did what I had to do. Usually it was, I’ll have sex if you let me sleep at your house and feed me and maybe give me some money.” Then drugs became a factor — crack and crystal meth. He gradually began partying less; he and Deutzman even swore off alcohol two years ago. “We just decided, we’re done,” Raven O said. “My big weakness now is sugar. And I do have a fried chicken fetish.”

There will likely be fewer personal revelations on an album Raven O recently recorded with the bassist Ben Allison, another longtime collaborator. It will be titled “Piece of Sky,” he said, after one of two original songs; the other tracks include standards and “some surprises, contemporary songs we made into jazz songs.” Painting, an old hobby that Raven O picked up again while hosting the Cirque du Soleil show “Zumanity” in Las Vegas, will provide another creative outlet. Arias had originated the Cirque part, “and Joey said, ‘If you ever give up performing, you should paint.’ I said I would never give up performing, but here we are.”

Should the stem cell therapy work well enough, Raven O wouldn’t rule out a return to the stage. “But I’d never do it as intensely,” he said. “In Hawaii, I can let nature take care of me. My older brother told me, you have to come home and let the aina — the island — heal you. And he’s a badass, too.”