Bolles began his career in 1915, when he was hired by the Dell Publishing Company to paint front covers for its line of spicy pulp magazines. He, like many other pin-up artists of the early Deco era, found a ready-made audience among the mostly male readership of the pulps. Film Fun was the pin-up magazine that immortalized the Bolles name. From 1921 to 1948, it carried his cover-art pin-ups which the American public came to recognize almost as much as the Petty Girl from Esquire. Bolles worked for many other pulps, including Coy Book and Cupid's Capers, which invited him to design their inaugural covers, and Spicy Stories, which had the biggest circulation among such magazines.

Bolles' pin-up girls were fun-loving and sexy, often provocative in their poses but occasionally caught in embarrassed or slightly self-conscious moods. Usually full of energy and brimming with health and a sense of adventure, they had almost childlike faces that contrasted with their sensual bodies. Bolles often incorporated Art Deco backgrounds, spotlights and other props, and clothing such as flimsy negligees and wet bathing suits into his work.

The wide variety of primary colours he employed was notable at a time when many of his contemporaries were using much more subdued tonal schemes. Although Bolles was a prolific artist, only a handful of his original paintings exist today.

Very little is known about Bolles' life. Probably born in the Chicago area, he worked in New York City, where he could be near the many publishing houses specializing in pulps and racy men's magazines in the 1920s and 1930s. It is rumoured that Bolles had emotional problems near the end of his life that led him to over paint some of his Film Fun covers, creating horrific expressions on his formerly fun-loving pin-up girls.