Not Your Bubbe's Yentl

 Long before Katy Perry gave the world faux bisexuality, singer-songwriter Jill Sobule offered up the real thing in her 1995 hit single, “I Kissed a Girl.” Sobule, who has 10 albums under her belt, has been asked whether she’s bisexual thousands of times in the years since (“Hmm, thinking queer sounds even more apropos than bi or gay,” she says after a conversation about her girlfriend of six years.) But these days Sobule is raising eyebrows even more with the world’s first retelling of Yentl in a way she’s envisioned since she read the Isaac Bashevis Singer short story “Yentl the Yeshiva Boy,” which inspired Barbra Streisand’s 1983 film.

“I really thought Yentl was a transgender boy,” she says, succinctly describing her Yentl, which is running at Sarasota, Fla.’s Asolo Repertory Theatre through April 26 (and has requests to play other cities, including London and San Francisco). Sobule’s Yentl is about a transgender boy’s coming-of-age rather than a straight girl’s secret. The singer composed all original songs for this new Yentl, giving the score a klezmer, folk, rock sound.

“I read it a long time ago, after seeing the movie when I was younger…” she recalls. “Back then there were no words for transgender, but I thought, Oh, this is really different than the Barbra movie. I mean, she feels like she’s a boy.”

Sobule, who worked closely with stage director Gordon Greenberg, wanted to tackle gender identity, sexuality, and the hormonal rush that the characters surely felt: “We forget that Yentl, because Barbra Streisand was like 40-something when she was in this, it was a coming-of-age story. It was raging hormones everywhere. There was confusion and sexual attraction all the way around.”

The Jewish musician interviewed both Jewish and transgender people for the score (her nonobservant family’s religious practices were like “Olive Garden compared to really good Italian restaurants”), including rabbis, Orthodox queers, trans men, and a trans woman who had to dress as a man at work in order to teach (“a real-life Yentl, but in reverse”).

“I did the best I could,” she says of trying to reflect transgender lives onstage. “I think if they would have asked any other songwriter for this, I don’t think there would have been that sensibility.”