James worked as a freelance illustrator and gig poster artist for a variety of musicians and events between 2013 and 2019 including Phish, Dave Matthews Band, Alabama Shakes, The Black Keys, Foo Fighters, The Jerry Garcia Foundation, Nine Inch Nails, My Morning Jacket, Sylvan Esso, Andrew Bird, Why?, Ray LaMontagne, Nickel Creek, Leon Bridges, Bonnaroo, Okeechobee and more.