Shapiro was born in New Jersey. Spending his early years in New York City and New Jersey, Shapiro started his career in the early 1980s as a Comedian at Catch A Rising Star on Broadway. Besides performing regularly on stage, throughout the 1990s he acted and starred in numerous films by Louis CK, including Tomorrow Night. Additionally, he portrayed the re-occurring character "Angry Poet" in Late Night with Conan O'Brien. In 1998, Shapiro released his first comedy-CD called Unconditional Love, which Billboard called "hard-edged and uncompromising".