Born in Barren County, Kenny got into music as a teenager. While attending the University of Kentucky for engineering, he started playing in bands. After graduation, he was offered the chance to join a touring band called Buster Brown. After touring, Kenny relocated to Bowling Green, working as an engineer by day and playing in various bands at night. He eventually focused full-time on music, working as a touring blues musician. He served as the frontman of the Ken Smith Band, but had a hard time finding the right venue to play in. He eventually bought a space to create a new kind of venue, Picasso’s, that would attract a more artist-centered crowd. The venue soon became a hotspot for music, even getting national recognition as a great place to play or party. Many well known local musicians passed through Picasso’s, like Jonell Mosser, Government Cheese, Bill Lloyd and Jane Pearl.
Kenny remained in Bowling Green, working to promote tourism and entertainment through festivals and the promotion of New Grass music. He is most proud of his work with New Grass Revival, Kentucky Headhunters, Government Cheese. He credits Billy Vaughn and Sam Bush with helping him take music more seriously.