In 1990, Tom Green hosted a rap show on Ottawa's CHUO radio station. It was appropriately called Rap Show. In 1993 he renamed the show to "The Midnight Caller", and changed it's vocation to a call-in, talk/comedy show. The show had quite a cult following in Ottawa. People would call in to discuss different subjects Tom had chosen, or simply to talk about something else (that resulted in a lot of people being hung-up on, and a lot of absolute nonsense). One of the very cool things he used to do is organize late night soccer games on Parliament Hill (at 2AM!); try doing that at the White House.
A year later, the first episode of The Tom Green Show was airing on Rogers 22 community cable, and the rest is history.