Craig got his career started singing behind the superstar, Sting, at age 15 on the 1988 Amnesty International's Human Rights Now! tour. After playing around in the rock/pop arena for a while, he realized that wasn't where his passion was. Years later he discovered jazz.
First up was fronting a 15-piece big band in Florida, as well as owning a piano bar on Fort Lauderdale Beach. After managing such a big sound and even bigger shows, playing to packed houses of 2,000 and more, he wanted to pare down the players and concentrate more on the style and personality of the music and his voice.
Moving to Hood River, Oregon, and then Portland, he sang with an upright bass and piano player all over the Northwest, doing over 200 shows a year.