Heo Gyun was born in the city of Gangneung to Heo Yeop and his second wife (known only by her surname Kim 김). Heo Gyun's sister Heo Nanseolheon was a poet. Heo's family was of the noble (yangban) class (his father had been mayor of Gangneung) and as such Heo Gyun was afforded a solid education and in 1594 passed the nation's highest civil service exam. Under the strong influence of his tutor, Yi Dal 李達, Heo Gyun became a progressive and liberal thinker who dreamed of establishing a more progressive society by eliminating all bigoted and conservative elements in the social, literary, and political realms. Heo went on to serve the government of Joseon in such positions as Minister of the Board of Punishment and State Councillor. In the course of his political career he was exiled several times for involvement in political feuds and was ultimately executed on charges of treason during the reign of Prince Gwanghae.
Heo is often credited as the author of the famous Korean story Tale of Hong Gildong, which in many ways reflects his progressive thinking, although his authorship has been disputed.