[2] Born in Salem, Illinois, he was the son of Charles Heaton, a civil engineer from England, and Amy Robertson from Missouri.

[7] One drawing of the still incomplete but newly opened Auditorium Building for the 1888 Republican National Convention was reprinted fifty years later by the Tribune as an example of Heaton's skill.

The newspaper had him continue the Events of the Week drawings long after the exposition closed, and later published annual compilations in book form.

[8] These "pen pictures" as the Tribune labelled them were a series of contiguous panels, a bit like a comic strip, though without a continuous storyline.

Although his cartoons with The Inter Ocean began as wide-ranging commentaries on current events, he found his niche within the world of Chicago politics.

For this time period, he signed his work as "Harold Heaton" and often inserted a small crow into drawings as a trademark.

One cartoon, called "Merely a Passenger", won acclaim from a national group of bankers meeting in Washington, D.C. to lobby Congress for financial reform.

[16] However, a retrospective by a Chicago Tribune writer many years later claimed that though Heaton had good ideas, his style while at The Inter Ocean was out of date.

[26] He spent a year in the United Kingdom with the James Welch company, playing at the Comedy Theatre in the West End of London and on tour in England and Wales with The New Clown.

[29] After it closed in March 1904, he formed a three-person troupe,[fn 2] Harold Heaton & Company, which played a one-act farce of his own writing called The Rat on a vaudeville circuit.

Lady Jim had been purchased by Walter N. Lawrence in March 1906[37] as a vehicle for Hilda Spong,[38] with rehearsals starting in August.

[41][42] The New York Times was harsh and personal, asserting that "Harold Heaton" must be a nom de plume for a naive young girl, and disparaging Hilda Spong's acting.

[48] In 1911 he performed in a musical comedy called The Heart Breakers by Frank R. Adams and Will M. Hough, with songs by Harold Orlob and Melville Gideon, that ran for seven weeks.

For the next year Heaton continued to live in Chicago, appearing in and staging amateur productions for a variety of clubs, social groups, and Chautauqua assemblies.

At Chicago, critic Percy Hammond commiserated with Heaton's character losing the girl to the star, saying it was "no reward for a pleasant actor and a reformed cartoonist".

[54] He spent three years playing revivals with touring companies, before landing a character role in the Broadway version of Mozart in November 1926.

[57] Heaton was a featured player in two Broadway productions during the first half of 1932, Happy Landing[58] and The Boy Friend,[fn 3][59] both of which lasted less than a month.

[64] He had an active social life in 1890's Chicago, attending parties, balls, and the opera with such notables as Mrs. Fiske and Marshall Field.