Weiss grew up in Long Island, studying fashion and film at various New York colleges. While writing his debut work, Weiss eked out a living as a photographer and a club promoter. The critical plaudits for "Amongst Friends" (including comparisons to Scorsese and Singleton) earned Weiss a three-picture deal with Universal. As of 1997, however, he only had a few projects in development and had not completed a second feature. The darkly handsome director played a small role in his own film and appeared as himself in Barry Levinson's 1994 show-biz film "Jimmy Hollywood."