He is best known for a series of sketchbooks and 35mm photographs documenting years of itinerant traveling around the United States and painting realistic depictions of 21st century America.
[4][5] During the early 2010s, Perry gained recognition for his series of sketchbooks and photographs collected while traveling around the United States by hitchhiking and riding freight trains.
[6][7] His large-scale works and posters have called attention to various social causes through collaborations with groups such as AptArts, No More Deaths, and the UN High Commissioner For Refugees.
[18] In 2018, Perry had his first museum exhibition, titled National Lilypond Songs, at the Urban Institute for Contemporary Art in Grand Rapids, Michigan.
[21] In 2021, Perry debuted Sensemaking, which depicted quiet scenes framed through roadside vantage points and performances of costumed figures and contemporary symbols.