[1] Montgomery left college to begin his career as a make-up artist, working for several major modeling agencies in New York City,[1] and for a number of prominent fashion magazines,[2] including WWD,[3] Glamour, Mademoiselle, Seventeen, and Cosmopolitan.
[5] He employed several techniques including one where his own photographic portraits were transferred to canvas and overlaid with paint or plastic, frequently making use of vibrant color in the process.
"[2] In March 2008 Village Voice columnist Michael Musto reviewed a book of Montgomery's unique portraiture, POP: Art Inspired by New York's Own Subcultures from Celebrity to Subway: Something More through Color and Light.
"[6] In addition to more everyday themes, such as a multi-canvas study of the tellers of his local bank,[2] Olan made himself known for his takes on celebrities, including images of Boy George,[6] Justin Bond,[6] and Rufus Wainwright,[6] as well as Anne Hathaway,[1] and Courtney Love.
[5] Beginning with a 2011 appearance in Boardwalk Empire, Montgomery found a place as a supporting actor in a lengthy series of television shows and feature films.
I would hope that the work be remembered as a moment in pop culture when the importance of the individual became relevant and no longer reduced and devalued like washing powders and news headlines.