Chuck Woolery originally set his sights on a career in the music industry but had a change of heart when he joined the U.S. Navy instead. After two years military service, he attended college in his home state of Kentucky and afterward held various jobs including a stint as a sales rep at Pillsbury. He later moved to Nashville where he formed the rock band "Avant Garde". He has one daughter and an adopted son from his first marriage, and one daughter from his second marriage and two boys from his third marriage.