A telling thing happens as Josh Dolgin, the Montreal musical performance artist who goes by the moniker "Socalled," sits down to talk about his two latest projects. Dolgin spent the winter creating a soundtrack album for The Season, his first musical, which premiered at Pop Montreal in 2011. And while he was doing that, he was also busy finishing up writing Tales from Odessa, his next musical, which opens June 16.

As we're sitting in a cafe in Montreal's Mile End neighbourhood, Dolgin is spotted by the artistic director of another theatre company, who offers a card and insists they must set up a meeting. "It'd be great to talk about a collaboration," he tells Dolgin.

It's a not-unusual encounter for Dolgin, who has a penchant for creating strange cultural alliances and fusions, and turning them into something new. Over the past decade, he's made an international countercultural name for his melding of traditional klezmer music with hip hop, a marriage he insists has never been that odd, given the similarities of both camps' beats, tempos and rhythms. It led some to call him the Yiddish James Brown.

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It also culminated in Dolgin being the subject of a feature-length documentary, Garry Beitel's 2010 The Socalled Movie, in which Dolgin suggests that perhaps he's "the Mahatma Gandhi of hip hop … except not as skinny." It's a typical bit of self-mockery, something Dolgin often resorts to while discussing his latest creative trajectory, the Yiddish musical.

"I think the first two bits of music I remember are something by Bach and then West Side Story ," he recalls. "I mean, they're a guilty pleasure. Because most musicals suck."

The new work is based on a short story collection by Isaak Babel, who wrote about Jewish gangsters in the Soviet Union at the turn of the 20th century. It's a grittier premise than his first foray, The Season, which tells the story of the impossible love that blooms between a forest animal and an extraterrestrial. It's a beautifully nutty story, and just to match form with content, Dolgin tells it with a cast comprised primarily of puppets.

"That happened by accident," he insists. "I had some fur kicking around and decided to slap some eyeballs on it. I was just doing it for fun, but a lot of my hobbies end up being my jobs. They found a place in my ridiculous universe."

The Season was born after Dolgin was approached by the Pop Montreal to create something, anything, new. "I thought this would be a great opportunity to write an original musical." And the leap from the form he's become so closely associated with, klezmer, is not such a leap, as he points out.

"Klezmer is at the heart of Broadway. Every single major Broadway composer was Jewish, and that means they would grow up with klezmer music. That culture, which I connected with through hip hop, has really informed my music and these musicals." The emotional complexity of klezmer, as Dolgin sees it, lends itself perfectly to the musical. "Klezmer music gives you hope and makes you smile, but it brings you back down to earth at the same time. They say it laughs and cries at the same time."

Bringing together an eclectic ensemble from Montreal's artistic milieu – including actor Joe Cobden, Montreal Symphony Orchestra harpist Jennifer Swartz, the string quartet The Warhol Dervish and renowned funk musician Fred Wesley (who wrote the overture), Dolgin crafted a musical that stands out for being oddly moving. It earned a standing ovation at its one-night run.

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And that one-night rush led Dolgin to "fight the ephemerality" by recording a live studio album to tape. He reassembled the original cast and musicians and, with the help of Grammy-winner Mark Lawson, created the album at Arcade Fire's Petite Eglise studio in Farnham, Que.

When Segal Centre artistic producer Paul Flicker saw The Season, he immediately saw the possibilities for another musical collaboration with Dolgin. "There's always been a very theatrical element to his schtick," Flicker says. "His understanding and knowledge of the musical form is amazing."

Dolgin told Flicker he'd been thinking a great deal about Jewish gangsters. "I was always a bit frustrated that there wasn't a great Jewish gangster story. There are some great Jewish gangsters in The Godfather II and Miller's Crossing , but then there's something like Once Upon a Time in America, with music by Morricone and starring Robert De Niro. He's obviously a great actor, but not Jewish. There were in fact Jewish gangsters."

It's Dolgin's formal innovation and reinvention that has earned him praise from industry insiders and critics alike. "What I like about his work is that it is both rigorously musical and literate but also very playful and flexible," says Henry Sapoznik, author and expert on klezmer music. "His overall cultural literacy, which includes film, literature, and pop culture, means he can, and does, make smart and telling platforms upon which to offer his musical explorations."

Dolgin concedes there's a strange irony to his own practice and the challenges musical artists face today. While so much of the music he has created involves sampling (he recalls the "all great art is stolen" line), the music industry's business models have been shattered thanks to the all-content-is-now-free nature of the Internet.

"You have to see it for what it is. You are never going to sell records like they used to sell records. There are crazy opportunities that arise as a result of the Internet. But it's a little frustrating what's happened to the idea of intellectual property. We still need that. People still want to read your article or listen to my song, and they can, for free, and that's amazing. I mean, I download my ass off all the time, and I'm constantly consuming all this amazing stuff. But I know that the people who created it need to and should be supported."

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At 36, Dolgin says he "can't quite believe where the last 10 years have gone," given his hectic pace. "I feel like I've just grown up enough to do the things I loved looking at as a kid. I painted the pictures for the book that accompanies The Season album. I made the puppets for the show. I get to write about love stories and gangsters, and work with puppets. I feel like I've found the confidence and skills to do the things I admired as a kid."

Tales from Odessa runs from June 16-July 7 at Montreal's Segal Centre.

Special to The Globe and Mail