He originally started as a disc jockey for a New York station playing rock music. He discovered a talent for comedy, and developed a wide-ranging confrontational style that encouraged listeners to call in. Eventually, in the 1990s, his show was widely distributed. As an example, in one of his most infamous episodes, he persuaded a female caller to have phone sex with him on the air. He made deep buzzing noises into his microphone, and had her sit on a speaker with the volume turned up.