Cliff Berryman was born in Kentucky in 1869. Berryman started as as draughtsman in the United States Postal Service but joined the Washington Evening Post as a political cartoonist in 1896. He became the chief political cartoonist of the newspaper in 1907.
Berryman was joined by his son, James Berryman, in 1935 and for the next fourteen years the two men contributed alternative daily cartoons.
Cliff Berryman, who was awarded the Pulitzer Prize in 1943, carried on working for the Washington Evening Post until his death in 1949.