He served as the Chair of the English Department at Vanderbilt University in Nashville, Tennessee for thirty years from 1912 to 1942, and he taught many members of the Fugitives and the Southern Agrarians, two literary movements in the South.
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As an active member of the Southern Agrarians group based in Nashville, Owsley contributed "The Irrepressible Conflict" to the manifesto I'll Take My Stand (1930).