Howard Stern
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.