The patriarch of the Berryman family, Clifford Kennedy Berryman, was born in Versailles, Kentucky, in 1869. His first job was in the U.S. Patent Office in Washington, D.C. He became a cartoonist for the Washington Post in 1891. From 1907, until his death in 1949, Clifford Berryman was political cartoonist for the Washington Star, earning a reputation as the "Dean of American Cartoonist," and winning a Pulitzer Prize in 1944. His cartoon of Theodore Roosevelt, "Drawing the Line in Mississippi," 1902, began the American Teddy Bear craze, and created Berryman's cartoon trademark. He was also the first cartoonist to become president of the Gridiron Club. His wife, Kate, was an avid member of the Daughters of the American Revolution.
Their daughter, Florence Berryman, 1900-1992, abandoned her study of music because of a loss of hearing and turned her attention to art. In the 1920s, she became a free-lance local art critic, writing articles for newspapers. She later assisted Leila Mechlin, as an art critic for the Washington Star. In 1946, Florence Berryman succeeded Mechlin and worked for the Star until her retirement in 1961. She also served as editor for the American Federation of Arts until 1944.
Clifford and Kate Berryman's son, James Thomas Berryman, 1902-1976, attended George Washington University and the Corcoran School of Art. He worked as a reporter for the New Mexico State Tribune, until his return, in 1923, to Washington, D.C. because of his mother's illness. He worked at the Washington Star, as an editorial artist and illustrator, until 1933, when he became a sports cartoonist. When his father suffered a storke in 1935, Jim intermittently drew political cartoons for the STAR. Jim Berryman also won a Pulitzer Prize for his political cartoons.