High school in Columbia began in the 1880s, and by 1889, Columbia established a two-year high school. The course of study was adjusted to three years to meet state standards in 1895, and to four years in 1896. Extracurricular activities naturally evolved. A literary society was formed in 1898, and choral union, orchestra, and debate team were established the following year. Sports teams were already present, although the district did not provide paid coaches.
Soon overcrowding at Columbia High School became a concern. In 1909, the community approved the demolition of the old school at 9th and Rogers and the building of a new high school on that site. The new structure had the district's first gymnasium and physical education credit was added to graduation requirements. A coach was employed to work with the athletic teams and an art/music teacher was hired. The first edition of the yearbook, the Cresset, was published in 1912. Commercial studies, teacher training, home economics, and mechanical drawing courses were added to the curriculum in 1913.
Following the war, Columbia continued to grow. In 1925, the community decided to build a new high school, this time on the country property of the David H. Hickman estate. Construction began soon after, and Hickman High School opened in 1927. Students in the high school manual trades program built some of the furniture used to furnish the new school.
During World War II, curricular changes reflected the times; courses in international relations, aeronautics, and home nursing were added. Hickman participated in a massive fund-raising drive for the war effort and collected salvage items. Driver's education was offered for the first time in 1948, and the tradition of requiring sophomores to wear beanies was restored.
In 1960, Hickman established an honors program to add rigor to its academics. The green and white sophomore beanies were worn for the last time in 1961.David Wheeler was named Hickman's first Presidential Scholar in 1964, the inaugural year of the national recognition program. The Kewpies finally beat the Jefferson City Jays in football in 1966, and four state championships in three different sports proved Hickman an intimidating opponent.
National recognition came to Hickman in the 1980s, as Hickman was chosen to receive the Excellence in Education (Blue Ribbon) Award in 1984-85. President Ronald Reagan visited Hickman in 1987, and two students (Missouri's quota) were tapped as Presidential Scholars in 1988.
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