D.C. searches for Mr. Nice Jewish Boy

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Mr. Nice Jewish Boy Pageant contestants, from left, Sam Rubinstein, Tony Cohn, Mike Sexton and Jeremy Gilston get ready to take the stage at Town Danceboutique in Washington. Photo courtesy of Jordan Lantz.

When Sam Rubinstein decided to be a contestant in the Mr. Nice Jewish Boy Pageant, he thought dressing in drag would be a cakewalk.

“I didn’t fully appreciate what I was getting myself into and spent considerably more time then I realized,” said Rubinstein, 22, who is a strategic engagement fellow at the American Constitution Society.


The makeup alone took three hours to apply. Then there was learning the lyrics to Ariana Grande’s “Greedy.” And mastering the art of walking in high heels. Friends of friends helped him select an outfit, which he topped with a curly brown wig. Dressing in drag, he decided, is harder than it looks.

“I have a newfound appreciation for the time-consuming work drag queens go through,” he said.

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Yet there he was, one of four gay Jewish men who took to the stage on Aug. 13 at Town Danceboutique, an LGBTQ nightclub in Washington, to compete in the Mr. Nice Jewish Boy Pageant, which raised $1,800 for local Jewish LGBTQ groups.

Rubinstein, along with fellow contestants Jeremy Gilston, Mike Sexton and Tony Cohn, had each prepared a self-promotional YouTube video to garner as many likes as possible. They demonstrated a talent and answered a series of questions. The winner was determined by judges’ scores, votes from the 150-member audience and the number of likes their video received.


The LGBTQ organizations Nice Jewish Boys DC and Nice Jewish Girls DC, sponsored the event with GLOE — the LGBTQ outreach program at the Edlavitch DC Jewish Community Center and the DC Center for the LGBT Community.

Rubinstein said the video was easy to make. In it, he talks about why he wants to win the competition and tries on a bra, a dress and other women’s clothes to preview to his act.

Gilston, who is 24 and works in real estate, said he played a klezmer medley on the clarinet for his talent, which landed him the second-place finish.

Sexton, a 24-year old national security analyst, danced and said he earned “third place at best.” But, he said, he was happy to be there.

“I think it’s a good display of the community coming together and doing good work,” he said. “It was a lot of fun to participate in.”

Cohn, 24, who hosts the Smithsonian podcast “Sidedoor,” said he had reservations about getting involved in the contest, but did so because it would help the LGBTQ organizations.

“Initially I was hesitant because I never saw myself doing beauty pageants, but when I saw what it was benefiting I felt an obligation to do my part,” he said.

Cohn drove with friends to Ocean City to make his video, in which he read from a script they wrote during the car ride.

“As we were on the beach and on the dock and at different restaurants, my friends would say, ‘Go through the script,’ and we filmed 10 to 15 videos of me saying the same script,” he said.

Cohn’s friends spliced together the clips to make a 45-second video. In it, Cohn introduces himself while cooking, running along the side of a road and riding in a car, all the while encouraging people to attend the pageant.

On stage, Cohn performed a rap about being Jewish that he said was inspired by the Broadway musical “Hamilton.”

“People sometimes ask what being Jewish means to me / and to be honest, it comes down to my incredibly amazing family / valuing tradition and living with compassion / and dreaming of that day I’ll be in love and glass bashing,” he rapped. And he concluded by smashing a glass, as in a Jewish wedding.

The rap helped Cohn (last week’s You Should Know in WJW) emerge with the crown as Mr. Nice Jewish Boy 2017, as did his answer to the question, “How would a date night with you be different from all other nights?”

Said Cohn, “I said I would make sure my partner sat in a chair with a cushion and ate only the most bitter herb.”

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