Jackson was born in Tennessee. He developed an interest in art from an early age, while watching his grandfather paint. Jackson went on to study art at the University of Tennessee with the intention of being a painter. However, at the suggestion of one of his teachers, he switched from fine arts to commercial illustration.
After graduation, Jackson moved to Nashville where he started working as an art designer. Eventually, he founded Jackson Design, a company dedicated to commercial art design. His company enjoyed success, winning several Grammy Awards and producing art for hundreds of albums.
After 20 years, Jackson decided to pursue his love of fine arts. He sold his business and started painting and sculpting. He is currently represented by Zeitgeist Gallery.