Born on Manhattan’s Upper West Side, Ostrovsky describes himself as “super gay as a youth” despite being a heterosexual male. He has publicly stated that his dreams were to own a house on Shelter Island, have a life partner, and do tasteful floral arrangements. He attended Skidmore College and New York University but was expelled from both before enrolling at the State University of New York at Albany, a state school that he admittedly chose as performance art, “to hang out with Italian dudes who had never met a Jew… just for the LOLs.”
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Known for his outlandish antics Ostrovsky worked on the E! Channel as a correspondent interviewing celebrities and was a member of genre-bending rap group Team Facelift, who was signed to Duckdown Records. The group’s sound was described by the New York Post as a cross between Barbra Streisand and Wu-Tang Clan. He has also been linked to DJ/ Producer Dillon Francis, appearing as part of his raucous live show.
After the group’s disbandment in 2010, Ostrovsky left music and began focusing solely on comedy and plus-size modeling. His pet Cavalier King Charles Spaniel Toast also has a sizable social media presence on Instagram, appearing at many fashion events and having her own line of accessories. He appears as a contributor on Bloomberg Television, has created video campaigns for such brands as Virgin Mobile and Burger King, and has a rabid cult-like social media following. In 2014 Ostrovsky confirmed that he had sold two shows to Comedy Central and Amazon, and is set to release a book entitled Money, Pizza, Respect this year under the Grand Central Publishing imprint.
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