On October 11, 1939, Governor
Lloyd C. Stark appointed Hollingsworth as a judge of the Missouri Eleventh Judicial Circuit. Hollingsworth was then re-elected to that office in 1940 and 1946. In August 1950, Governor
Forrest Smith elevated Hollingsworth to a seat on the state supreme court vacated by the death of
Albert M. Clark. In 1952, Hollingsworth was re-elected to a twelve year term on the court, serving for a total of 14 years, including a two-year stint as chief justice, from July 1958 to April 1960. He had planned to step down at the end of 1964. ==Personal life and death==