Webster received his BFA from the School of the Art Institute of Chicago and his MFA from the Mason Gross School of the Arts, Rutgers University. He also attended the Skowhegan School of Painting and Sculpture. Webster is the recipient of numerous awards including the NYFA Fellowship in Painting, the Pollock Krasner and the Golden Foundation Individual Artist Award. He has shown in solo and group exhibitions in New York at Blackston Gallery, Transmitter Gallery, Sara Meltzer Gallery and White Columns, among others. He has been awarded residencies at Nes Artist Residency, the Marie Walsh Sharpe Space Program, Painting Space 122, Virginia Commonwealth University, The Ucross Foundation, The Corporation of Yaddo, The Ragdale Foundation and The MacDowell Colony.