Harold Gray, Original Creator of Little Orphan Annie

May 30, 2010


Oval, blank eyes look back from the page at the reader, not giving any sense of the spunk that took Annie safely from one adventure to another. Harold Gray debuted Little Orphan Annie in 1924, a little girl that captured comics readers' hearts. After 85 years, Annie retired from print on June 13, 2010, but that girl is not finished with the limelight just yet...

Cartoonist Harold Gray  

Born in Kankakee, Ilinois on January 20, 1894, Harold Lincoln Gray grew up apparently interested in science. In 1917, he earned a Bachelor of Science engineering degree from Perdue University. A Lafayette newspaper gave Gray his first job out of school, then the young man was detoured by a stint in the army as a bayonet instructor during World War One.

After the war, Gray accepted a job with the Chicago Tribune's art department at $15 week salary. He moved up to an assistant post with "The Gumps" cartoonist, Sydney Smith. Gray also began developing strip ideas of his own, submitting and receiving rejections for four years, said William Dunn in Ron Goulart's The Encyclopedia of American Comics, from 1897 to the Present (Promised Land Productions, New York 1990).


Gray created an adventure strip with a sturdy, brave child hero called Little Orphan Otto, and submitted the comic strip to Captain Joseph Medill Patterson, then editor with the Chicago Tribune Syndicate. The cartoonist's strength was not in the art - his drawings were considered stiff, primitive and without grace - but he was a true master at telling a story. Captain Patterson told Gray to make the lead character a girl instead, and the strip was accepted into syndication.

Debuting in newspapers on August 5, 1924, Little Orphan Annie featured a girl struggling in the classic rags-to-riches tale, with a big dose of the cartoonist's political views added. After offending several newspapers and having the strips removed, Gray learned to temper his "strongly conservative views", but said Dunn, "the strip was often controversial."


After a few weeks in print, Gray added a character that would take on a life of his own. "Oliver Daddy Warbucks" adopted Annie from the Orphanage. The good life for Annie would only last for a while, then she was in danger or on a grand adventure. Fending for herself in the big world with her dog, Sandy, Annie always kept a bright outlook until she got herself out of the mess and found her adoptive father again.

The Little Orphan Annie comic strip was so popular with readers that on one occasion when the instalment was left out of the daily newspaper, the error "caused more rumpus on the Tribune switchboard than a world war, a big league baseball game or the bombing of the post office," said Phil Rosenthal in the Chicago Tribune, May 12, 2010.

1995 US Postage, Little Orphan Annie  
Little Orphan Annie Collection, Book 1

The success of Little Orphan Annie enabled Gray to syndicate another comic strip, "Maw Green". In it, Gray made statements on life and politics from an Irish point of view. "Maw Green" ran until Gray died in 1968. (Gray was against gas rationing, welfare, income taxes and other policies of the day.)

Knowing his artistic skills were unusual for a cartoonist, Gray siad, I know what I want and do the best I can." The blank eyes of characters in Little Orphan Annie almost became Gray's signature, leaving the reader to interpret the mood themselves. Working generally on his own, Gray employed his cousins Edwin and Robert Leffington as his assistants, only for lettering and background work. Edwin became a cartoonist in his own right in 1933 with his creation, "Little Joe". When Edwin died in 1936, his brother Robert took over "Little Joe" until it ended in the late 1950s.


Gray described his Annie character as "tougher than hell, with a heart of gold and a fast left, who can take care of herself because she has to." The cartoonist became a multi-millionaire from his creation. Annie was transformed into a radio personality for 13 years beginning in the 1930s; she was on the movie screen for the first time in 1932 and again in 1938. The Little Orphan Annie storylines were a good fit for comic books, and along with appearing in "Dell's Super Comics from 1939-49," said Don Markstein of "Don Markstein's Toonopedia," Annie also appeared in her own comic books from 1937 to 1948.

Little Orphan Annie became a star in the many musical versions of "Annie" on stage and in movie theatres, and has been very popular in a range of licenced merchandise. The Broadway musical "Annie" kept performers busy and audiences entertained for over 2,000 performances, running from 1977 to 1983. The United States Postal Service honoured Little Orphan Annie and many other comics with 32-cent postage in their 1995 "Classic Comic Strips" series.

Published in newspapers for almost 86 years, the comic featuring the requisite Annie curls, red dress and white cuffs came to an end with the last Sunday feature on June 13th, 2010. Over the years, Little Orphan Annie dwindled down in newspapers, appearing in only about 20 publications. This is not the end of Annie, though, but perhaps a beginning. Her stories will continue on in new media, theatre, graphic novels, book collections of the strip, and much more.


Harold Gray died on May 9, 1968 in Lajolla, California. After a stint of five years trying to find suitable cartoonists and reprinting old issues of the strip, Little Orphan Annie carried proudly on in her true durable style, under the skilled hands of Leonard Starr for 20 years. Starr retired in 2000. Two fresh talents took on the drawing, writing, and updating of Annie's adventures, Andrew Pepoy and Jay Maeder.

Well, Annie, we won't be seeing you in the funny pages when the sun comes out tomorrow, but we will be seeing you in a lot of other places. We'll be waiting for you.

* Art and cartoonist's photo are the property of Tribune Media Services, stamp property of USPS.

Little Orphan Annie Collection, Book 3  
© Susanna McLeod 2010