Born in Riverside, Connecticut and raised in New Rochelle, New York, Raymond's first cartoons were published in his high school newspaper.

In 1938, Chic Young returned from his sabbatical, resuming his place as the main writer of Blondie.

Raymond continued to play a major role in creating the artwork, in addition to a short stint assisting his brother Alex on Jungle Jim around 1944.

In 1950, due to Chic's diminishing eyesight, Raymond permanently became the lead artist of Blondie and began to develop the distinctive style that the strip uses to this day.

Chic Young died in 1973 and his son Dean, who had been assisting with the writing for about ten years, took over as head writer.