It was eight years after Riley's death when Gray created his comic strip Little Orphan Otto (1924), and the Chicago Tribune's Joseph Patterson changed the title to Little Orphan Annie. Three years later, King Features came up with their own waif, Little Annie Rooney.
In Gray's storyline, Annie was an orphan whose only friends were her doll Emily Marie and later her dog Sandy. Her main physical characteristics are a mop of red, curly hair , a red dress and vacant circles for eyes. Her catch phrases are "Gee whiskers" and "Leapin' lizards!" Annie attributed her lasting youthfulness to the fact that she was born on Leap Day, February 29, and so only aged one year in appearance for every four years that passed.
She escaped from a Dickensian orphanage and made her way in the world by pluck, hard work and a cheery disposition. In 1925, she met Oliver Warbucks, an idealized capitalist who, at that time, resembled Jiggs of Bringing Up Father. Although Annie had been taken on trial by Warbuck's wife, it is he who showed her the most affection, insisting, on their first meeting, that she call him "Daddy".
However, Annie did not get on with Mrs. Warbucks and, feeling that she simply caused misery, ran away from home. (Later, Mrs. Warbucks reformed her spoiled ways, and still later disappeared from the strip, never to be mentioned again.) Annie would be separated from Daddy Warbucks on many occasions, but always returned.
The name "War-bucks" appears to describe how Daddy made his fortune. After Annie (and maybe Sandy) he is the most important character in the strip. He earned his money by hard work and hates snobbery. He is tough but fair and pays his workers well. His servants love him. Warbucks is bald-headed, wears a tuxedo and a diamond stickpin in the middle of his white shirt.
Other major characters, introduced later in the strip, include Warbucks' right-hand men, Punjab, an eight-foot native of India, introduced in 1935, and the Asp, an inscrutably generalized East Asian, who first appeared in 1937.
There was also the mysterious Mister Am, a friend of Warbuck's who wore a Santa Claus-like beard and was of a jovial personality. He claimed to have lived for millions of years and even had supernatural powers. Some strips hinted that he may even be God.
At first, the comic was humorous, aimed at children. Through the 1920s, the stories became more adventurous. By 1931, the strip was being read by many adults, and became more political. Story lines included one where Daddy Warbucks lost all his money, then lost his eyesight, then was thrown into prison. Annie had to fare for herself in a cold, cruel world.
Warbucks was able to bounce back, but subsequent stories would devise various ways to separate Annie from Daddy, leaving her to fend for herself. Then Annie would hit the road, until Daddy showed up again. Often she was taken in by a poor but honest family.
After Gray's death in 1968, the strip continued under other cartoonists (including Gray's assistant Tex Blaisdell and David Lettick) but was replaced with reruns in 1974. Following the success of the Broadway musical Annie, the strip was resurrected in 1979 as Annie by Leonard Starr, creator of Mary Perkins, On Stage, and the only one besides Gray to achieve notable success with the strip.
In 1995, Little Orphan Annie was one of 20 American comic strips included in the Comic Strip Classics series of commemorative U.S. postage stamps.
Upon Starr's retirement in 2000, he was succeeded by New York Daily News writer Jay Maeder and artist Andrew Pepoy, beginning Monday, June 5, 2000. Pepoy was eventually succeeded by Alan Kupperberg (2002-2004) and Ted Slampyak (2004-).
By the 1930s, the strip had taken on a more adult and adventurous feel with Annie coming across killers, gangsters, spies and saboteurs.
It was also about this time that Gray, whose politics seem to be either conservative or libertarian, introduced some of his more controversial storylines. He would look into the darker aspects of human nature, such as greed and treachery. The gap between rich and poor was an important theme.
The strip (and Gray, in interviews) glorified the American business ethic of an honest day's work for an honest day's pay. His hatred of labor unions was dramatized in the 1935 story "Eonite". Other targets were the New Deal and communism. Corrupt businessmen often appeared as villains.
Gray was especially critical of the justice system, which he saw as not doing enough to deal with criminals. Thus, some of his storylines featured people unashamedly taking the law into their own hands.
This happened as early as 1927 in an adventure named "The Haunted House". In it, Annie is kidnapped by a gangster called Mister Mack. Warbucks rescues her and takes Mack and his gang into custody. He then contacts a local senator who owes him a favor. Warbucks persuades the politician to use his influence with the judge and make sure that the trial goes their way and that Mack and his men get their just deserts. Even Annie questions the use of such methods but concludes that "with all th' crooks usin' pull an' money to get off, I guess 'bout th' only way to get 'em punished is for honest police like "Daddy" to use pull an' money an' gun-men too, an' beat them at their own game".
Warbucks became much more ruthless in later years. After catching yet another gang of Annie kidnappers he announced that he "wouldn't think of troubling the police with you boys". The implication was that while Warbucks and Annie celebrated their reunion, the Asp and his men took the gang away to be lynched.
In another Sunday strip, published during the Second World War, a war-profiteer expresses the hope that the conflict would last another twenty years. An outraged member of the public physically assaults the man for his opinion, claiming revenge for his two sons who have already been killed in the fighting. When a passing policeman is about to intervene, Annie talks him out of it suggesting that "it's better some times to let folks settle some questions by what you might call democratic processes".
These views caused outrage from many quarters. The New Republic was especially critical, publishing an article by Richard L. Neuberger which described Annie as "Hooverism in the Funnies". A later editorial went further in describing it as "Fascism in the Funnies".
In real-life the idea caught on and schools and parents were encouraged to set up similar groups. It is claimed that Boston alone had 20,000 Junior Commandos by late 1942.
From 1931 to 1933, the radio show had two different casts, one in Chicago and one in San Francisco, performing the same scripts daily. Floy Hughes portrayed Annie in the West Coast version.
Little Orphan Annie began in 1930 in Chicago on WGN, and on April 6, 1931, with Ovaltine as the sponsor, the 15-minute series graduated to the Blue Network. Airing six days a week at 5:45pm, it was the first late-afternoon children's radio serial, and as such, it created a sensation with its youthful listeners, continuing until October 30, 1936. During a contract dispute with Shirley Bell, Annie was briefly played by Bobbe Dean in 1934-35. Pierre Andre was the show's announcer.
The show opened with a theme song that took on a popularity of its own with oft-quoted lyrics:
The song led to the catch phrase, "Arf says Sandy," sometimes given as "Arf goes Sandy." With Ovaltine still on board as sponsor, NBC carried the show from November 2 1936 until January 19, 1940, and concurrent broadcasts were also carried at 5:30pm on Mutual in 1937-38. In 1940, Ovaltine dropped sponsorship of the show to pick up Captain Midnight, an aviation oriented show more in tune with the increasing international tensions as World War II started in Europe and the Orient.
Sponsored by Quaker Puffed Wheat Sparkies, the show moved to Mutual for its final run from January 22 1940 to April 26, 1942. Janice Gilbert portrayed Annie from 1940 to 1942. A new character, Captain Sparks, a dashing aviator, was introduced, and Annie became his sidekick. Despite the program's popularity, few episodes have survived.
In 1977, Little Orphan Annie became a Broadway musical, Annie, with music by Charles Strouse, lyrics by Martin Charnin and book by Thomas Meehan. The original production ran from April 21, 1977 to January 2, 1983. There have been other international productions, and the musical has been filmed several times, notably the 1982 version directed by John Huston and starring Albert Finney as Warbucks, Aileen Quinn as Annie, Ann Reinking as Grace Farrell (Warbucks's secretary) and Carol Burnett as Miss Hannigan, matron of the orphanage. The story took considerable liberties from the strips, such as having Oliver Warbucks visit Franklin D. Roosevelt at his home and reluctantly support his New Deal. Harold Gray deeply loathed Roosevelt and at one point killed the Warbucks character, declaring that he could not live in the current climate. Upon Roosevelt's death he suddenly brought Warbucks back, proclaiming that the air had changed.
The Broadway Annies were Andrea McArdle, Shelley Bruce, Sarah Jessica Parker, Allison Smith and Alyson Kirk. Notable actresses who portrayed Miss Hannigan are Dorothy Loudon, Alice Ghostley, Betty Hutton, Ruth Kobart, Marcia Lewis, June Havoc, Nell Carter and Sally Struthers. Famous songs from the musical include "Tomorrow" and "It's the Hard Knock Life."
The 1980s children's television program You Can't Do That on Television in its later banned "Adoption" episode, parodied the character as "Little Orphan Andrea". Andrea, like Annie, sported curly red hair and a red dress but unlike her, was a very naughty orphan who had a habit of beating up other kids. A less well-known (or rather, notorious) example was the 'Daddy Fleshbucks' side-story from American Flagg!. The title was parodied in The Simpsons' episode Little Orphan Millie. In the early 1970s, a flavored ice treat for children called Otter Pops (with cartoon otters as flavored mascots such as "Alexander the Grape") featured a character dubbed "Little Orphan Orange."
Considering both Cupples & Leon and Pacific Comics Club, the biggest gap is in 1928.