With a mother who was an art teacher, and a father who made a career as a drafting instructor, Jon Whitcomb was predestined to have superior artistic talents. Having plenty of access to art supplies as a child, Jon's interest in drawing began at an early age and steadily grew over the years until he finally decided to make art his profession. Eventually attending Ohio Wesleyan University and Ohio State, Jon did pictures for school publications and posters for a local theatre company. Upon graduation, he worked for various studios doing advertising, travel and theatre posters. Moving to New York in the early 1930s, Whitcomb had developed his colorful, simple, direct style, especially in rendering the perfect glamorous American woman image.

Always able to portray the latest in dress fashions and elegant decor, he excelled in numerous magazines, including Good Housekeeping, The Saturday Evening Post, Cosmopolitan, and Collier's. When World War II broke out, Whitcomb was a lieutenant in the Navy, doing his duty as a mine sweeper before the military discovered his drawing skills and transferred him to the Pacific as a combat artist. After the war, Jon did a series of monthly articles and sketches starring the latest motion picture stars for Cosmopolitan as well as their covers and other spot illustrations. Sometimes working as much as 18 hours in a single day to accomplish all his writing and illustration duties, Whitcomb lived and worked in his beautiful home with studio in Darien, CT.