Cherry received his BFA from Northern Arizona University where he began painting as a figural artist exploring domestic narratives. After receiving his MFA from the School of the Art Institute of Chicago where he attended with the Presidential Fellowship, he set up his studio practice and began to exhibit around Chicago and the Midwest in galleries such as Lyons-Wier, Gescheidle, and fifty-50.
He has taught and guest lectured at: School of the Art Institute of Chicago, Ox-Bow, the University of Chicago, the Evanston Art Center, and Pennsylvania College of Art and Design. His solo exhibition at Pennsylvania College of Art and Design debuted his titan-sized nude portraits entitled someBODIES. He has served as Dean of English, Fine Arts, and Humanities at South Suburban College; and Academic Dean at Pennsylvania College of Art and Design. He is currently Associate Professor and Chair of the Fine Arts and Foundation departments here at the College of Art and Design. His work has been featured in several volumes of New American Paintings and in multiple issues of Poets and Artists.