Bailey started acting in commercials at the age of two. Some national television commercials starring Bailey include Priceline. com, Clorox, Stouffer's, Juicy Juice, BMW, Bissell, and Mucinex. He guest starred in his first role, Strong Medicine in 2005 as Dougie Nauls. He co-starred in NBC's pilot Alpha Mom. He also starred in such television shows as Criminal Minds, How I Met Your Mother and Numb3rs.