Gray grew up on a farm near the small town of Chebanse, Illinois. He graduated from Purdue University with a degree in engineering, but as an artist, he was largely self-taught. A former letterer for Sidney Smith on The Gumps, he came up with a strip idea in 1924 for Little Orphan Otto. The title was quickly altered by Chicago Tribune editor Joseph Medill Patterson to Little Orphan Annie.
By the 1930s this strip had evolved from a crudely-drawn melodrama to a crisply rendered atmospheric story with novelistic plot threads. The dialogue consisted mainly of meditations on Gray's own deeply conservative political philosophy.
Gray sometimes ghosted Little Joe (1933-72), the strip by his assistant (and cousin) Ed Leffingwell which was continued by Ed's brother Robert. Maw Green, a spin-off of Annie was published as a topper to Little Orphan Annie. It mixed vaudeville timing with the same deeply conservative attitudes as Annie.
Harold Gray was a charter member of Lombard Masonic Lodge #1098, A.F. & A.M. in 1923.
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