Watstein, a prominent figure in the film industry, was born in the picturesque neighborhood of Far Rockaway, Brooklyn, in the year 1970. His educational background is marked by attendance at the prestigious Tisch School of the Arts, located at New York University. In addition to his academic pursuits, Watstein's professional journey also includes a decade-long tenure as a waiter at the renowned Barney Greengrass on the Upper West Side. The proprietors of this esteemed establishment, Gary and the late Moe Greengrass, have been instrumental in supporting Watstein's cinematic endeavors.
Watstein's paternal lineage is equally noteworthy, with his father, Joel, being a celebrated bluegrass banjo virtuoso who regularly performs in the vibrant music scene of Greenwich Village.