Watstein, a truly remarkable individual, was born in the vibrant and bustling neighborhood of Far Rockaway, Brooklyn, in the year 1970. This remarkable event marked the beginning of a life that would be filled with creativity, passion, and a strong sense of determination. His educational journey was truly one of a kind, as he had the privilege of attending the prestigious Tisch School of the Arts at New York University. It was here that he honed his skills and laid the foundation for his future endeavors, no doubt influenced by the esteemed faculty and the rich cultural atmosphere of the university. Interestingly, Watstein's professional life began to take shape when he started working as a waiter at the iconic Barney Greengrass on the Upper West Side, a position he held for an impressive ten years. This remarkable tenure allowed him to develop a strong work ethic, build lasting relationships with his colleagues and customers, and gain valuable experience that would serve him well in his future pursuits. It is worth noting that the owners of the esteemed establishment, Gary and the late Moe Greengrass, have been instrumental in supporting Watstein's film career, showcasing their dedication to nurturing his talent and providing him with the resources and guidance necessary to achieve his goals.
Watstein's family heritage is steeped in musical tradition, with his father, Joel, being a celebrated virtuoso of the bluegrass banjo, whose remarkable talent has captivated audiences for years in the vibrant and eclectic environment of Greenwich Village, a hub of artistic expression and cultural diversity.