Little Orphan Annie was initally a daily comic strip created by Harold Gray (below) and syndicated by Tribune Media Service. 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 a popularity in a Fortune  
magazine poll in 1937. The strip’s popularity began to decline over the years and 
and was running in only 20 newspapers when it was cancelled on June 13, 2010.

Harold Gray

First Little Orphan Annie Sunday newspaper comic strip, November 2, 1924.