As a young man, Claude Crockett studied cartooning through a correspondence course. In 1933, he started drawing for the Washington Evening Star, under the direction of fellow cartoonist Jim Berryman. Initially Crockett drew illustrations, gag and sports cartoons. In the 1940s, Crockett's work began to alternate with Berryman's on the editorial page. Eventually, Crockett replaced him as editorial cartoonist in 1965 upon Berryman's retirement. Crockett's illustrations promoting war bonds were recognized by the U.S. Treasury. He won the National Headliners Club Award for consistently outstanding editorial cartoons in 1953.