Glassman starred in the role of Burski on the NBC sitcom Undateable and wrote, directed and starred in the NBC-produced web series spin-off The Sixth Lead. He played the role of Harold Ramis in the film A Futile and Stupid Gesture, a biopic about the National Lampoon and starred in the Amazon Prime Video comedy drama series As We See It.
Glassman was born in Shaker Heights, Ohio, a suburb of Cleveland, and grew up in the suburb of Orange. His father, Steve, was a restaurateur before becoming part owner of a carpet store in Mayfield Heights in the late 1990s.
Glassman attended Orange High School, graduating in 2002. He was on the high school basketball team and his team played against St. Vincent–St. Mary High School, whose team was led at the time by LeBron James at the time. He graduated from Kent State University in 2006 with a degree in marketing. He was also taking theater classes while at school. After graduation, Glassman considered going to law school, but started performing stand-up comedy, first performing at the Cleveland Improv.

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