Weston became enamored with the sport of boxing at the age of 10 after his father brought home a copy of "The Ring" magazine. At the age of 13, Weston met neighbor and "The Ring" founder Nat Fleischer and later landed a summer job as a stock boy at the publication. Weston was soon colorizing black and white portraits of boxing figures with oils. In December 1939, Weston, a budding artist, painted a portrait of Billy Conn that would be the first of 57 "Ring" covers. Daughter Toby Weston Cone said of her father, he "never liked going to boxing matches but was extremely interested in the sport. He felt it paralleled life in many ways."