Gregory is originally from Phoenix. He became interested in design and color in his early years. He became serious about art while studying history at Clark University. While at Clark, he visited the museums of Boston, such as Gardner, Harvard Fogg and the Museum of Fine Arts. It was at these museums he found the inspiration to make artwork of his own. He enhanced his art training at the Laguna School of Art, graduating with a BFA degree and then continuing on to get his MFA at Claremont College. For his Master Project, Gregory completed a series of seascapes of Venice Beach during different times of the day throughout the year. This technique is called Plein Air. This style of painting has continued to be Gregory's primary technique since. Gregory also frequently paints human figure and folk tale subject. His pieces are usually long and narrow suggesting the horizontality of land, sea and sky. Using this horizontality, he includes visualizing a specific scene through a series of changeable moods of season, light and weather. Gregory has exhibited in numerous single and group exhibitions throughout the southland.