Vintage Chicago Tribune newsletter
The Vintage Tribune newsletter is a deep dive into the Chicago Tribune’s archives featuring photos and stories about the people, places and events that shape the city’s past, present and future.

Vintage Chicago Tribune

Thursday, August 7, 2025

A “Little Orphan Annie” comic published in the Chicago Tribune on Sept. 27, 1942. (Bill Hogan/Chicago Tribune)

A quick trip to Stratford Festival’s performance of “Annie” produced one of the most magical moments in the life of my 10-year-old — his introduction to the song, “Tomorrow.”

It reminded me of my reaction to hearing it for the first time in the 1982 film, which starred Aileen Quinn as the moppet in a red dress with a white collar.

Annie’s adventures and antics began 101 years ago this week in the New York Daily News.

Here are highlights from her journey that probably was inspired by a folk tale, then found itself in the pages of the Tribune before the curly-haired character burst from the newspaper onto Broadway and then the big screen.

1885

“Little Orphant Annie” told the cautionary tale in James Whitcomb Riley’s 1885 poem that if a child misbehaved, then ” … the Gobble-uns ‘ll git you / Ef you Don’t Watch Out!” (Chicago Tribune)

The rhyme “Little Orphant Annie” by “Hoosier Poet” James Whitcomb Riley was told by an orphan (named Annie) sent to a farmer’s home to earn her keep by washing dishes, sweeping and baking during the day. At night, however, she told stories to the farmer’s children warning them they would be taken away by elves, goblins and witches if they were naughty.

A decade later, Richard Felton Outcault’s character “The Yellow Kid” — considered the first comic published in an American newspaper — debuted. He became an instant sensation, spawning a raft of products and stunning the industry.

The Tribune — which had been running four pages of Sunday comics since 1895, but not in color and with no continuing characters — soon looked for ways to incorporate more visuals.

The paper hired John T. McCutcheon in June 1903 as its regular editorial cartoonist. (His first front-page illustration for the Tribune appeared on July 1, 1903.)

Feb. 12, 1917

On Feb. 12, 1917, “The Gumps,” by cartoonist Sidney Smith, made its appearance in daily strip form in the pages of the Chicago Tribune; it was soon picked up for national distribution by the newly created Tribune-News Syndicate. (Chicago Tribune)

“The Gumps,” by Sidney Smith — for decades one of the most popular comic strips — was introduced in the Tribune. Smith signed in 1922, the first million-dollar contract ever given a comic strip artist. “The Gumps” was published until 1959, and outlived its creator, who was killed in a car crash in 1935.

1918

Joseph Medill, center, is surrounded by his grandchildren Robert McCormick, from left, Eleanor Patterson, Medill McCormick and Joseph Patterson. McCormick and his cousin Joseph Patterson started the Tribune syndicate. (Chicago Tribune archive)

“The Gumps” helped to lay the foundation for the Tribune syndicate (now Tribune Content Agency), which, under various names, was a money-making endeavor that would spread comic strips and other editorial products to newspapers across the world. Joseph Medill Patterson, cousin to Col. Robert McCormick and founder of the New York Daily News tabloid, led the way.

Patterson helped create and nourish, among many other strips, “Gasoline Alley,” “Moon Mullins” and “Terry and the Pirates.” He was energetically hands-on, offering advice, coaching artists and coming up with ideas to promote the strips. He would regularly assemble his cartoonists to discuss characters and story lines.

In his 1959 book “Comic Art in America,” Stephen Becker wrote: “It is probably true that no other publisher in history … took as much interest in the comics he published as Patterson did. … The Tribune and the News did not dominate the twenties; yet of the dozen enduring strips created in that decade, half are their products. (They were) essential in the transition from comics as an adjunct to journalism to comics as a profession in itself.”

Early 1924

Harold Gray, the creator of the “Little Orphan Annie” comic strip in the Chicago Tribune, circa 1946. (Chicago Tribune historical photo)

Born in Kankakee but raised in Indiana, Harold Gray had no formal art training. He did, however, have a degree from Purdue and came to Chicago to meet fellow alum McCutcheon in hopes of securing a job at the Tribune. He spent a short time as a cub reporter, but was hired as an assistant to Smith on “The Gumps” after World War I.

Aug. 5, 1924

The first published comic strip of “Little Orphan Annie” was in the New York Daily News on Aug. 5, 1924. (Daily News)

Daily News readers were introduced to Gray’s Annie, the feisty yet lovable pre-teen girl with no mother or father. Miss Asthma ran the big city orphanage where she lived.

“At the time, little boy strips were all the rage,” Gray told the Tribune in 1946. “That’s one reason I decided on a little girl. I chose an orphan because I didn’t want to get involved with a lot of extraneous relatives. I wanted a simple story built around a character who would be as real to readers as Annie was to me.”

Annie was Gray’s only child, since he had none of his own. Unlike Riley’s poem, however, the comic strip’s target audience was not children.

“It isn’t the kids who buy the papers, it’s their parents,” Gray said.

Sept. 27, 1924

The Oliver “Daddy” Warbucks character first appeared in the comic strip “Little Orphan Annie” on Sept. 27, 1924, in the New York Daily News. (Daily News)

By then a regular feature, the brash billionaire Oliver “Daddy” Warbucks — who didn’t know an orphan could be a girl — appeared in the comic strip for the first time and was instantly smitten with his adopted daughter.

Nov. 2, 1924

The first “Little Orphan Annie” comic strip published on a Sunday, Nov. 2, 1924, in the Chicago Tribune. (Chicago Tribune)

Annie pulled at the heartstrings of Tribune readers for the first time. “Leapin’ lizards” became a household term.

“Three days before the country’s headlines flashed ‘COOLIDGE WINS,’ America’s comic-reading public came home from church, put the roast beef in the oven, and settled into a comfortable Sunday routine with the funny papers,” Tribune reporter Norma Lee Browning wrote 22 years later.

Oct. 27, 1925

On Oct. 28, 1925, the Chicago Tribune apologized on the front page for missing a day of the popular comic strip “Little Orphan Annie.” (Chicago Tribune)

Pandemonium ensued when Annie was left out of the Tribune. Irate readers called the paper to find out what happened to their beloved comic strip character. One person threatened to bomb the newly completed Tribune Tower if Annie didn’t reappear.

On Oct. 28, 1925, the Chicago Tribune apologized on the front page for missing a day of the popular comic strip “Little Orphan Annie.” The Tribune published two, four-panel strips on that day to make up for the error. (Chicago Tribune)

To appease the public, Tribune editors printed two Annie strips — plus a front-page apology — the next day. The Tribune’s explanation: Concern that Annie was getting too big for her britches.

“Annie was behaving herself right democratic like, what with salad forks and all,” the Tribune reported. “But it was thought that possibly she might be getting just a bit ritzy.”

Jan. 5, 1925

The first time Sandy the dog appears in the “Little Orphan Annie” comic on Jan. 5, 1925. (Chicago Tribune)

Sandy, Annie’s dog, was introduced. The dog was the only character in the strip that aged.

1930

The Chicago Tribune announces on Dec. 27, 1930, the Little Orphan Annie radio show will be on WGN, broadcast from the Drake Hotel and sponsored by Ovaltine. (Chicago Tribune)

Annie finally had a voice, courtesy of South Side native Shirley Bell Cole. “Little Orphan Annie” premiered on WGN radio as a 15-minute show sponsored by Ovaltine. It was the first time the character was targeted to children, who collected decoder rings and pins to decipher cryptic messages revealed by Annie. The radio program aired until 1942.

May 9, 1968

Harold Gray, shown here in an undated photo, was the creator of “Little Orphan Annie” for almost 44 years, producing the plots, dialog, character studies and drawings almost entirely by himself. (Chicago Tribune archive)

Gray died in La Jolla, California, at 74. At the time of his death, another 12 weeks of the strip had been prepared. But no clear succession was detailed. Cartoonist Leonard Starr picked it up in 1979.

April 21, 1977

“Sandy,” left, takes a delicate chomp out of a spoonful of ice cream held by co-star Andrea McArdle during a party the cast of the Broadway musical “Annie” gave the youngsters of the Henry Street Settlement House in New York on Aug. 4, 1977. McArdle portrays the cartoon character Little Orphan Annie in the show, while “Sandy” plays her canine sidekick. (Suzanne Vlamis/AP)

Two years after the Tribune dropped “Annie” from its comics pages, the young orphan debuted on Broadway at the Alvin Theatre (now the Neil Simon) in New York. Andrea McArdle (“a self-assured teenager who only came to read the comic strip after she won the title role,” the Tribune reported) and Reid Shelton (who played the Warbucks role with a full head of hair until the director suggested he shave it for more realism) starred.

McArdle received a Tony nomination for Best Lead Actress in a Musical, according to Playbill, but the award went to her co-star Dorothy Loudon, who portrayed Miss Hannigan.

“Annie” spent six years — 2,377 performances — on Broadway.

May 18, 1982

First lady Nancy Reagan shown with actress Aileen Quinn, 10, who plays Annie in the movie musical “Annie,” at the premier of the movie in New York’s Radio City Music Hall on May 18, 1982. Annieís dog, Sandy, watches the festivities at the benefit showing. (G. Paul Burnett/AP)

The highly anticipated movie of the summer, “Annie” starred Aileen Quinn as the orphan and Albert Finney as Warbucks.

John Huston, director of “The Maltese Falcon,” “The Treasure of the Sierra Madre” and “The African Queen,” created a “powerfully poignant portrait of a wealthy man — the billionaire, right-wing, munitions magnate Oliver Warbucks — who learns that what he really wants out of life is to be a father, to have someone to love and to be loved in return,” Tribune critic Gene Siskel wrote in his review of “Annie.”

One key change from the Broadway musical: The ending no longer included a Christmas scene — where Annie’s trademark red dress with white collar was revealed for the first time — since snow would have been cost-prohibitive. Instead, it’s a Fourth of July party.

Siskel gave the film just