Cunningham began his career as the art department coordinator on the 1995 science fiction thriller Species (which featured Jordan Lund, David Selburg, William Utay and Herta Ware in the cast). His art department team on this film included DS9/Star Trek: First Contact illustrator Ricardo Delgado and veteran Star Trek foreman Tom Talley. Cunningham then worked as a set designer and assistant art director on several films before becoming a full-fledged art director. His early set design work could be seen in such films as The Baby-Sitters Club (featuring Bruce Davison, Scarlett Pomers, and Harris Yulin), A Time to Kill (featuring Ashley Judd and Kurtwood Smith), and That Thing You Do! (featuring Bill Cobbs, Clint Howard, Holmes Osborne, and Sean Whalen).