Cole apprenticed under the legendary Will Eisner during his early days. In 1940 he had learnt much of the fundamentals of narrative illustrating and was handling the art chores for The Spirit[?] strip.
In 1941 Cole created Plastic Man for Police Comics. A few years later in 1943 the idiosyncratic character gained his own title. Plastic Man's offbeat humor and his ability to take any shape gave the cartoonist many opportunities for experimentation in both text and graphics.
Plastic Man had been a crook named Eel O'Brien when he fell into a vat of acid. He was saved by a mysterious order of monks who cured his penchant for crime. The acid bath gave him the ability to change his shape. He wore dark glasses and a red and yellow costume as flexible as his body. Whatever shape he took, the colors remained the same, so there would be a red-and-yellow chandelier over a table full of plotting gangsters, or a red-and-yellow abstract painting hanging on the wall.
Cole continued to work on his wildly popular character for many years and also became the premiere illustrator for Playboy magazine. His elaborately finished cartoons set the style for all the cartoons in the magazine. In 1956 Cole left the Plastic Man title. Two years later on August 15, 1958 Cole took his own life.