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Little Orphan Annie was a daily American comic strip created by Harold Gray (1894–1968) and syndicated by Tribune Media Services. The strip took its name from the 1885 poem "Little Orphant Annie" by James Whitcomb Riley, and made its debut on August 5, 1924 in the New York Daily News. It ranked number one in popularity in a Fortune poll in 1937.

The plot follows the wide-ranging adventures of Annie, her dog Sandy, and her benefactor Oliver "Daddy" Warbucks. Secondary characters include Punjab, the Asp and Mr. Am. The strip attracted adult readers with political commentary that targeted (among other things) organized labor, the New Deal and communism.

Following Gray's death in 1968, several artists drew the strip and, for a time, "classic" strips were rerun. Little Orphan Annie inspired a radio show in 1930, film adaptations by RKO in 1932 and Paramount in 1938 and a Broadway musical Annie in 1977. The strip's popularity declined over the years and was running in only 20 newspapers when it was cancelled on June 13, 2010.

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