Throughout the 1930s, Bergey worked freelance for a number of publishing houses. His eye-catching paintings were predominantly featured as covers on a wide array of pulp magazines, including romance ("Thrilling Love", "Popular Love", "Love Romances") as well as detective, adventure, aviation, and Westerns. Bergey illustrated mainstream publications, such as "The Saturday Evening Post", during this time. He illustrated covers for fitness magazines. Along with pin-up painting peers such as Enoch Bolles and H.J. Ward, Earle K. Bergey was one of the first prominent American pin-up artists, contributing hundreds of covers to influential magazines including "Gay Book Magazine", "Pep Stories", and "Snappy".