“You can never stop wearing masks,” said Lipa Schmeltzer, eyes on everything but the road, “you can only choose what mask you want to wear.” A few hours into a recent day, Schmeltzer had taken off his entertainer mask—through which he constantly posed and smiled and shouted, to make others laugh—and transformed into a proud Columbia University student. (“I never even heard of the Ivy Leagues!” he said.) His love of “secular knowledge” burst forth like a broken dam. Here was Schmeltzer, quoting an important essay about the nature of identity. “That’s from an essay I’m reading, by Wendy Doniger,” he said, referring to her essay “Many Masks, Many Selves.” “I love the way she writes.”The idea was to capture a typical day in the life of the most recognizable Orthodox Jewish singer in the world, a man whose “Mizrach” music video garnered more than 1.4 million views on YouTube, a Jewish figure who appeals to all types of Jews, regardless of gender, affiliation, belief, or politics. Raised ultra-Orthodox in the Skverer sect, Schmeltzer quietly left his community in 2010, when he moved from New Square to Airmont, New York. He remained Orthodox and observant but no longer follows the strict rules of the sect he grew up in, especially in regard to secular studies and interactions with women and non-Jews, among other lifestyle choices. Now at the end of his second semester at Columbia University—secular higher education remains a rare occurrence for Skverer Hasidim—he was embarking on a new stage of his already storied life, exploring the boundaries and capabilities of a fluid religious identity.Schmeltzer in a single day goes often from Jewish enclave to Jewish enclave, and on the day we spent together last February, he went from Monsey to New Square to Airmont and then from Flatbush to Borough Park to Williamsburg, ending up in the Lower East side and then finally Columbia before returning to his house. On the way, he discussed: Jewish academia, the legacy of the Holocaust, the relationship of non-Jews to Hasidim, Steve Jobs, the nature of progress, classical music, opera, the subconscious, ars poetica, music therapy, dance, the trauma of his past, his hopes for his and his family’s future, the downside and pleasures of fame, and modern literature. “A friend told me to read this book by a secular Jewish writer,” he explained. “I don’t remember the name of the book, but it’s famous. Has a lot of short stories and one long one.” “Goodbye, Columbus,” I guessed, citing Philip Roth’s famous collection. “Yes!” he said, as if recapturing a cherished memory. “What an interesting book!”Though he was open about his past, revealing himself in a flurry of interviews, he expressed a desire to move past the pain associated with his leaving the Skverer fold, though he accepted that it defined his trajectory. As a restless, musical youth, he found an outlet in performing publicly after he married. His natural talents—he has a dynamic, expressive voice and is a jittery, exciting dancer—catapulted him to a certain kind of fame in the insular world of Hasidic wedding music. His popularity grew with his jovial antics, his lighthearted, humorous music videos, and a willingness to use non-Jewish music mixed in with his own. The New York Daily News dubbed him the “Jewish Elvis”; other outlets described him as “the Jewish Lady Gaga.” Both may be true, to the extent that you can compare Jewish music to the magnitude of those pop stars, but he also bears some interesting comparisons to Kanye West.With 13 solo records to his name, and many other collaborations, he has made his stamp on the sprawling world of Jewish music. Given his openness, and given his readiness to push boundaries, Schmeltzer has also been the target of threats of censure, or condemnation, by rabbinical authorities who see in his vibrancy a threat to their religious dignity. In 2008, for example, Schmeltzer found himself in outright conflict over “The Big Event,” then scheduled for Madison Square Garden’s WaMu theater. In anticipation, A group of right-wing Rabbis took out a full-page ad in Hamodia to announce “a serious prohibition to attend or perform” at the concert, for fear that it would lead to “ribaldry and lightheadedness.” Performers were also blacklisted, with rabbis making it forbidden to hire singers on the Big Event bill “to sing at any party, celebration, or charity event.” Schmeltzer still felt the sting from this controversy and many smaller ones in which rabbis and community leaders attempted to coerce him into changing his music or style. “It’s taken years,” he explained, to move past this rancor.After spending 24 hours with Schmeltzer, I found it hard not to think of Walt Whitman’s proclamation, “I contain multitudes.” Schmeltzer displayed a very American desire to change and choose, to wear new masks and inhabit them. To converse with Schmeltzer was to speak with an explosive personality emerging from years of self-described cages and rigid lines. Taking us back to the neighborhood of his youth, he highlighted the street signs announcing—in Yiddish of course—a block as for men or women only. Like others who have left the fold, Schmeltzer stood on a strange cliff, the world blooming for him. We captured a day in that life.Photographs by Avia Moore.Joseph Winkler, a freelance writer living in New York, is a contributor to vol1brooklyn and The Rumpus.