Pepitone was born to a Sicilian father and a Jewish mother in Brooklyn, New York City, and was raised from the age of nine on Staten Island. His father was a history teacher and later the dean of a high school.[3] As a child, he would often make his friends laugh, describing himself as a “classic class clown” and would incorporate the use of word play and non sequiturs. While his mother was supportive of his career choice, his father wanted him to become a doctor. His father, involved with the Teachers Union, gave him a copy of The Rich and the Super Rich by Ferdinand Lundberg. Prior to becoming a comedian, he installed hardwood flooring, which he claims caused tinnitus that affects him today. He also developed a hernia while working on hardwood floors.