Born in Wallula, Kansas, Bailey studied at the Kansas City Art Institute under Randall Davey, Charles Wilimovsky and Thomas Hart Benton. He served as the Editor and Art Director of the Kansas City Times between 1917 and 1927. He later settled in California where he worked as a motion picture artist and served as Art Editor of the Los Angeles Herald Examiner.

He also spent time in New Mexico where he taught a Master Class in Taos between 1927-29.