Harold Lincoln Gray, the son of Ira L. Gray and Estella M. Rosencrans, was born in Kankakee, Illinois, on January 20, 1894. His parents both died before he finished school in West Lafayette, Indiana, where the family had moved.
He graduated from Public School in 1908, High School in 1912, and Purdue University with a degree in engineering in 1917. Along the way, he was selling cartoons to the local newspaper and farm journals while working hard construction jobs to pay his way through school. Upon graduation, he went to Chicago and became a cub reporter for the Chicago Tribune at $15 per week. He soon became a general handyman in the paper's art department, but left to do his time in the service.
When he returned, he worked for five years as an assistant to Sidney Smith, the creator of The Gumps, and learned his future trade from a master. He developed his own ideas for a comic strip, and met with Captain Joseph Medill Paterson to discuss its potential. Captain Paterson felt that there were enough young boy adventure strips and told Gray to put a skirt on the kid and call her Little Orphan Annie.
Little Orphan Annie debuted in the special pink edition of the New York Daily News on August 5, 1924.
Gray injected his own conservative beliefs into his strip. Little Orphan Annie was highly motivated, fiercely independent, minded her own business, and believed in action. In the years that followed, Gray created a family for Annie by introducing "Daddy" Warbucks in 1924, Sandy in 1925, Punjab in 1935 and The Asp in 1937.
Gray also experienced some changes in his personal life. His first wife, Doris C. Platt, died in late 1925. Four years later, he married Winifred Frost and they moved to Connecticut as the comic strip prospered. Later, they spent winters in La Jolla, California.
"Daddy" Warbucks and Harold Gray were diagnosed with cancer in 1967, and while "Daddy" beat it, Gray died of cancer on May 9, 1968 after a 44-year career of drawing and writing one of the world's greatest newspaper comic strips, Little Orphan Annie.