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Jason grew up in Wantagh, Long Island, and attended Wantagh High School, where he was involved in the school's music and drama programs. After graduating from Wantagh in 1994, Jason attended Cornell University, earning a degree in communications and honing his comedy skills as a member of the university's sketch group. After a move back downstate to New York City, Jason founded (and unceremoniously dissolved) two other sketch groups with several other former Cornellians, and also established a very brief, yet storied stand-up comedy career.