Jill Sobule: Singer, Songwriter and in Sarasota

Sobule will return to Asolo's Mertz Theatre Monday for a one-woman, one-night only concert.

Jill Sobule is many things — Yentl composer, blogger, provocateur, singer-songwriter, lesbian and '90s folk-rock star.

But she never saw herself as a teacher.

Sobule worked with Florida State University/ master of fine arts students to create songs for Asolo Rep's new staged musical of Yentl. But there's a teacher behind each student.

"At one point one of them says, 'Gosh, you've been our favorite teacher,' " Sobule told Patch in a phone interview.

“I’ve never thought of myself as a teacher or mentor, and that made me feel so good and made me feel this is the second half of this life. There's more."

Sobule, 47, will return to Asolo's Mertz Theatre Monday for a one-night only, one-woman concert at 8 p.m. Tickets are still available and range from $17 to $52. 

There will be a reception with Sobule on the mezzanine after the performance. Sobule is garnering a lot of attention for her new musical adaptation of Yentl, about a girl who lives as a young man to study the Talmud.

Reception tickets may be purchased for $10 through the box office or online. Those buying tickets at the $50 level will receive a pass to the reception at no additional charge.

Fans can expect, well, whatever Sobule thinks of at that minute.

"I wing it," she said. "Ninety-three percent, it's fantastic and spontaneous. Once in a while, I should have prepared something. I think it keeps it fresh, and I just start a song and feel where that will go and relate and feel what the audience wants next. It's a stream of consciousness."

The Greek chorus featured in , singing Sobule's songs, are expected to join her near the end of the set for a special performance. 

It's not just Sobule's second life from being considered a teacher that she'll bring with her to perform. It's her life and the lives of others.

Sobule, a self-described Tom Boy in her youth, would give dolls away to friends because she wanted to be one of the boys. 

"I wanted a football and guy things," she said, laughing. Her adolescence is a theme in her projects, including the off Broadway play, Prozac and the Platypus, the Nickelodeon show Unfabulous (which she wrote the theme song for), and her '90s hits, I Kissed a Girl and Supermodel, which appeared on the Clueless soundtrack. 

She's quite the researcher for collaborations, which is reflected in her interpretation of Yentl, based on Isaac Bashevis Singer's short story, Yentl the Yeshiva Boy. Though Jewish, Sobule used her research skills to gain a deeper understanding and appreciation of the religion and its cultural history.

"Sometimes I write biography songs like Mary Kay Letourneau, but here I really wanted to know this character," she said. "First of all, I'm Jewish, but I'm Jewish like is to Italian restaurants."

She talked to rabbis, friends, Orthodox Jews. She she even found a "real-life Yentl," a transgendered female rabbi. Those discussions informed her compositions for this new musical version of Yentl.

"I go overboard, and for me it's a learning experience and I almost go to school, even with the Bible," she said. "A couple songs are directly taken, and I stole from the Songs of Songs." 

Such as Jonathan and David in Yentl where she pens "Jonathan and David in the Book of Samuel. They were really close, if you know what I mean."


Known for her ability to analyze and offer commentary through song, it should be no surprise Sobule enjoys blogging.

She contributes to The Huffington Post. She's actually good friends with founder and editor, Arianna Huffington, and wrote a theme song for Huffington's On Becoming Fearless. Patch is part of The Huffington Post Media Group.

"She had me come to parties and sing with her. There’s a song where I had her rap in the middle. It was awful," she said, laughing. "I never had released it, but maybe I should now."

"Arianna? Amazing. We had to fix it and do it for two hours. It's not her forte," she said. 

Huffington is "kind of one of the people who intimidated me" trying to convince her to come out for a book party. "Uh, I really can't. I got a friend coming who's visiting," Sobule said she had told Huffington.

"In her Natashian accent from 'Rocky and Bullwinkle,' she says, 'Dahhling. You must come,'" Sobule said. 

Sobule's blogs, both on Huffington Post and her own website, gives her a chance to write about current topics and release political songs immediately she wouldn't normally write for a record.

"The old paradigm is you putting out a record and waiting six months for it come out," she said. "Now you can post something the moment you write it."

'You can't steal a live show'

So how do you make money if you're posting songs for free? 

"I sell drugs," Sobule said sardonically. "No, it's tough. It's like journalists and the day of the Internets posting stories hoping people will read them. [With music] hopefully it works out, you put something out, the more people get to know you, more people come to your shows."

It's the live shows that many performers tell you are where the check comes in.

"You can't pirate it. You can't steal a live show," she said. "People have to come to it. … It's kind of real old school. The reasons why people made records in the old days was to promote their shows."

Sobule is mixing old, new and well, middle schools in that approach.

In 2009, she created a website, Jill’s Next Record, and actually gained enough fan donations to pay for a record that wound up being California Years. Now she’s burning CDs for a new EP herself.

"I just burned 1,000 copies of this little EP I made to sell on tour of my social political songs since I don't have a brand new record for tour," she said. "In the old days, it would have to been through the record company and I make 50 cents off of it.

"Here, I burned it and am taking it on tour, and it's all mine. Most of the time, why would people buy a CD anymore? I don't buy CDs anymore. I use iTunes. But when you’re touring, it's a souvenir, and bands usually sign them."

Beyond Yentl

Beyond Sobule’s seven albums and additional EPs and Yentl, she’s continuing her craft, working on two collaborative projects. The first is another play.

“It’s called Times Square and taken from a pretty awful movie and cult movie from the late ‘70s called Times Square and takes place in 1970s New York,” Sobule said. “I listen to a lot of pre-punk music of that era in New York, and that’s a lot of fun.”

There’s also a project called Dottie’s Charm.

Her inspiration for it comes from a gift. Sobule has a charm given to her by friend Marykate, purchased on eBay. Ever the researcher, she learned the woman who owned it was named Dottie, and that she probably wore it in the ‘60s. Sobule's imagination, creativity and talent took over from there.

She decided give “charms” to favorite authors that she knew. These authors  weren’t known to write songs. But she hoped the charms would inspire them to pen some lyrics.

“They write a whole song about this women’s life with one the charms,” she said. Authors she’s working with on the project include Rick Mody, Jonathan Lethem, Luc Sante. “Rick Moody has the 'piano' charm and Luc Sante had 'the map of Kentucky,' ” she said.

The lyrics the authors have written turned out to have similar themes. “Where this Dottie is this charm-bracelet wearing woman and is sad-sacked and not a pretty girl and was always good,” she said. 

Who knows the future for Dottie's Charm. Right now, Sobule hopes that Yentl is the charmer for her.

“I would love it to move on. For me, you write a bunch of songs, I put them on a record and perform them and hear them,” she said. “It's playing for three months and it ends. You hope someone picks it up and (it) has a life after Sarasota, and I think it will.”

If you go

Tickets for both A Night with Jill Sobule and Yentl can be purchased by calling the Asolo Rep Box Office at 351-8000 or online at www.asolorep.org.


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