Gregory was born in the rural town of Dixon, IL in 1988 and has been creating artwork since his childhood. His drawings incorporate symbolism and an illustrative style to depict themes of mortality, Christianity, and nature. His work is inspired by comic book illustrations, folk art, and artists such as Edward Gorey, Gustave Dore, and Caspar David Friedrich.

Gregory is a printmaker also, and learned how to create multiple color serigraphs on his own through extensive trial and error. He is also currently attending Northern Illinois University to pursue a Masters of Art degree with a focus on printmaking. Gregory enjoys and thrives on the meticulous and process-oriented nature of printmaking. He takes great pride in creating original drawings and printing them with an eye for excellent craftsmanship. He has experience with the processes of serigraphy, intaglio, and relief.

Gregory received his B.S. degree in Art Education from Northern Illinois University in 2012 and is currently teaching drawing, ceramics, filmmaking, and printmaking at a high school in northern Illinois. He finds the experience of teaching art very rewarding. He finds the cyclical nature of teaching, learning from his students, creating art, and teaching integral to his art making process.