Known for his self-deprecating humor and stage presence, Hill has become a symbol of the growing transgender performance scene once just known as drag

The businessman from Connecticut seemed game for a different night of entertainment – a variety show of sorts. He took his seat at Joe’s Pub near an older couple from Long Island, exchanged pleasantries and then watched with amusement as Murray Hill, the drag “king of comedy”, came on stage and started his annual Academy Awards show monologue.

“What do you think of the suit?! What brand is it you say?” he asked of his grey vested duds, with 70s-era bow tie and blue ruffled tuxedo shirt. “Amazon Prime! With like 13 pairs of Spanx underneath. They’re like condoms for fat people!”

Hill then stopped and scanned the room, looking for a new, bemused face – the face not in on his joke. He found the guy from Connecticut. “But see, see this guy here? This guy is thinking, ‘Is this a man or a woman up there? Well, the answer is ‘no’.”

“Are you the warden from Orange is the New Black?” he asks him. “Whoever you are, this is going to be a long six hours.”

A former fixture of the downtown Village scene, Murray Hill is making a wing-tipped footprint in the mainstream arena, traversing stages, states and seas to find his next act, whether as an emcee to a burlesque show, a standup comedian, a film sidekick or a television personality. Riding on the success of such shows as RuPaul’s Drag Race, Hill’s success has also become emblematic of the burgeoning transgender performance scene, once just simply known as “drag”.

But make no mistake, “Mur’s a guy. End of story,” says Michael Musto, the former Village Voice culture columnist, who has been a fan of Hill’s since the beginning. “He is Mr Showbiz, the hardest working man in the biz and a true delight every time he hits the stage. His self-deprecating humor and entertaining skills are legendary by now.”

Helped along by Hill, or not, drag kings are, however, experiencing a resurgence from relative obscurity in the early 2000s and tearing up conventional gender norms. Troupes such as Switch n’ Play, a queer performance collective in Brooklyn, the DC Kings, who rule in the nation’s capital, and All the King’s Men from Boston, are capitalizing on the popularity and the trail-blazed paths of those before them, such as Hill and another Joe’s regular, Justin Vivian-Bond, who have completed their metamorphoses and now identify as trans-genre.

“We encourage men to get in touch with their femininity, to think about how to become mothers, to become more nurturing,” wrote scholar and queer theorist Jack (nee Judith) Halberstam in his book Female Masculinities. “But there is no encouragement for women to express their masculinity, and that’s because masculinity is a site of empowerment. The beauty of the drag king performance makes you aware how much masculinity is performative and theatrical. Murray Hill is transforming masculinity and exposing its theatricality with profound results.”

The entertainer persona of Busby Murray Gallagher, Murray Hill – based partly on Gallagher’s love for Benny Hill – started out in 1995 as a drag king, and became the then 26-year-old School of Visual Arts student’s graduate thesis: a full-time performance as a candidate running against Rudolph Giuliani for mayor on the drag king ticket. But in the last decade, Hill decided to no longer inhabit the persona of Gallagher (in public at least), eschewed the troupe mentality of the drag kings and decided to forge an individual name for himself.

“I am much more than a drag king. I really hammered the press about this and I finally got to a point where I think when people assume that somebody is queer, or different, or trans, they always want to put something before their name. And that is what drag king has been,” Hill told David Shankbone, an independent journalist in 2007. “Why can’t you just call me a comedian like Jerry Seinfeld is called a comedian?

Hill’s first foray into a regular performance gig became the eponymous Murray Hill Show at long-deceased East Village clubs such as as Fez, Mo Pitkin’s House of Satisfaction and The Zipper Factory. However, as clubs closed, the show evolved. A Murray Little Christmas, Murray Hill’s annual Miss LEZ Pageant and Murray Hill is 100% Polyester began showing to audiences of all stripes at Upright Citizen’s Brigade, Gotham Comedy Club, Comix and Caroline’s on Broadway. He started hosting burlesque shows at venues over the world including the London’s Arts Theatre and the Bloomsbury Ballroom, opening parties for the Venice Film Festival and making guest appearances on John Cameron Mitchell’s Shortbus and HBO’s Bored to Death.

“When I started out, downtown was anything below 14th Street – every single night on Ave A and B, there was something going on; it’s not concentrated like that any more,” Hill bemoaned over the phone the day before his packed Oscar act. “The home crowd doesn’t happen in the Village – now it’s in Bed-Stuy, or other parts of Brooklyn. When I perform in Manhattan, it’s for the rich people, not the cool kids.

I still go out of my way to stay connected with the roots,” he said, but his bio name-drops Le Tigre, the Beastie Boys, Clap Your Hands Say Yeah and Scissor Sisters, for whom he has appeared in music videos or emceed.

Even as the drag kings stage their comeback with showcases such as Beef (a Night of Manful Performances every month in Bushwick) and documentaries such as The Making of a King, don’t look for Murray Hill among them. Coming from Australia to do the Oscars Show at Joe’s, Murray is headed overseas again this spring for a round of burlesque in Europe.

“To me, Murray was always a standout. He always took being a drag king to a new level which was more fully realized than most kings. He’s a performer with a full act – not just someone who can deliver a lip-synch number,” said Lady Bunny, AKA John Ingle, a well-known drag queen, nightclub DJ and founder of the annual Wigstock event.

“The audience is in on the joke that Murray was born female, but the character is so charming that his personality and shtick overrides his sexual identity,” Ingle said.

“Interestingly enough, many drag kings gravitate towards playing the most boorish, sexist, cigar-smoking men. Murray is more cheesy than sleazy, and I think it makes him appeal to a wider audience.”

• This article was amended on 30 March 2016 to correct a misspelling of the name Murray. The article was amended further on 31 March 2016 to delete a reference to Hill’s previous name. We removed it out of sensitivity for Hill and his preference not to be referenced as a woman.

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