One could think of Riley's adventuresome youth as something out of a Huck Finn story.
When the Barnum and Bailey circus was performing, Bernard managed to earn a few dollars by gilding acrobats. In his eye, there was no activity more rewarding to a young artist than this direct contact with human flesh and greasepaint.
At Bridgeport's Central High School he became an industrious designer and builder of stage sets for the school's prize-winning plays. Riley painted signs, illustrated catalogues, arranged window displays, cartooned for local newspapers, and put his hands on anything offering him a creative challenge. He felt lucky to land a temporary job as a lab technician During the pit of the Great Depression. He spent the next 41 years working forty hours per week at this job, yet without sacrificing the precious time for his art.
While he was stationed at the Philadelphia Naval Hospital during World War II, Riley taught art to returning amputees as part of their rehabilitation. He credited the Navy for sending him to Temple University, where he was trained in surgical anatomy for purposes of physical therapy. Riley felt he gained a solid grounding in classical anatomy from his daily activities working with the handicapped, and from his anatomical studies with cadavers.