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She was an Ohio-born lady who could shoot like the dickens. She was the first white woman hired by a Wild West outfit to fill a traditionally male role. She was, hands down, the finest woman sharpshooting entertainer of all time. And, at one time, she may have been the most famous woman in the American West or the American East. She was, of course, Annie Oakley — her name nearly as well recognized to this day as that of the bigger-than-life figure who hired her, Buffalo Bill.

Annie, born Phoebe Ann Moses in Ohio’s Darke County on August 13, 1860, got her gun at an early age but didn’t shoot her way to everlasting fame until after William ‘Buffalo Bill’ Cody put her on the payroll in 1885. In the process, the little woman (5 feet tall, about 110 pounds) gave Cody’s Wild West a shot in the arm. As a star with the stature, ability and uniqueness of Buffalo Bill himself, Annie Oakley had a platform to promote her egalitarian views about women. She believed that women needed to learn to be proficient with firearms to defend themselves and that they could even help fight for their country. During World War I, she offered to recruit and train a regiment of women sharpshooters. If nothing else, Annie Oakley helped expand the career options of American women.

Annie rose to stardom from humble roots. In the mid-1860s her father, Jacob, died, and her mother, Susan, had a devil of a time trying to make ends meet with seven children age 15 or younger on her hands. Annie tried to help by hunting and trapping in the Darke County woods. By age 10, Annie had been sent off to live at the county poor farm, known as the Infirmary, and during her early teens she alternated between living there and with her mother and stepfather. Her life took a turn for the better when she met Irishman Frank (‘Jimmie’) Butler of the Butler and Baughman shooting act.

According to legend, Butler was trying to drum up business in 1875 by accepting challenges from local marksmen, and on Thanksgiving Day in Greenville, Ohio, he took on young Annie Moses in a shooting match. ‘I almost dropped dead when a slim girl in a short dress stepped out to the mark with me,’ Frank Butler later said. ‘I was a beaten man the moment she appeared.’ Frank lost, 23 to 21. Later, whenever he said that he had purposely thrown the match, Annie would just flutter her eyes and smile. In any case, Frank was impressed enough by Annie to invite her to see his act in Cincinnati. She accepted. As part of his act, Butler and his big white French poodle, George, performed a William Tell bit. As usual, Frank shot the apple off George’s head and George retrieved the fruit, but the dog then brought it to Annie instead of to the shooter. A courtship ensued — between Annie and Frank, that is — and the couple was married within the year…or so the legend has it.

Shirl Kasper, author of the 1992 biography Annie Oakley, points out that the shooting match couldn’t have occurred in 1875, because Frank Butler’s shooting career probably didn’t even start until 1876. There are no contemporary newspaper accounts of the match. More likely, it occurred in 1881, which is what Butler said several times much later. When the couple actually wed is also uncertain. They told everyone that they were married about a year after they met, and their only known marriage certificate says they tied the knot on June 20, 1882, in Windsor, Canada, when Annie was 21.

Annie joined Frank’s stage act, according to her own account, only after Frank’s shooting partner, John Graham, became ill in May 1882. She filled in admirably and became an instant hit. She chose ‘Oakley’ as her stage name for some unknown reason and began to tour with Frank. To the experienced showman’s credit, he immediately realized that his wife was a star. He put his own career on a backburner so that he could manage her career, saying, ‘She outclassed me.’

In those early days of her stage career, Annie Oakley played with Frank Butler at small theaters, skating rinks and circuses. While working for the Sells Brothers Circus in New Orleans in 1884, they met Buffalo Bill Cody, but he didn’t hire her until after she and her manager-husband had come to Louisville, Ky., early in 1885 for a three-day tryout. After an agreement was struck, Buffalo Bill brought her to the mess tent to introduce her to the members of his Wild West, which had been inaugurated in 1883. ‘This little missie here is Miss Annie Oakley,’ Buffalo Bill said. ‘She is to be the only white woman with our exhibition. And I want you boys to welcome and protect her.’ They didn’t need to — ‘Li’l Missie,’ as Cody usually called her, had pretty much fended for herself from childhood.

Annie Oakley and Frank Butler toured with the Wild West for some 16 seasons, and the only contract they had with Cody was verbal. Annie said that Cody, whom she called ‘the Colonel,’ was the kindest-hearted, most loyal man she had ever met, and also the softest touch. She noted that Cody kept a big pitcher of lemonade by his tent so that he could serve refreshments to visiting youngsters. The Oakley act was spectacular. Cody generally used Li’l Missie early in his entertainment extravaganza so that she could warm the audience up to the sound of gunfire. Dexter Fellows, a sometimes press agent for the Wild West, wrote in his autobiographical book This Way to the Big Show that Annie ‘was a consummate actress, with a personality that made itself felt as soon as she entered the arena.’ During her entrance, Annie waved and blew kisses to the audience. She was an ambidextrous shot who fired rapidly and with unerring accuracy. On the rare occasions when she missed a shot, she immediately fired again. On occasion, she intentionally missed and then pretended to become petulant, stamping her feet in frustration and sometimes throwing her hat down and walking around it to change her luck. Then when she did hit the mark, the audience would roar louder than ever.

Frank Butler also got into the act, releasing clay pigeons for his wife. She would jump over her gun table and shoot the clay bird before it hit the ground. Often she shot cigarettes out of her husband’s mouth, and once she even shot a cigarette out of Kaiser Wilhelm II’s mouth. Charlatan shooters preferred to shoot ashes from cigars (with the help of a wire embedded in the cigar and twisted by the assistant’s tongue at the proper moment), so Annie insisted on shooting only whole cigarettes. Her act often included hitting targets while riding a bicycle with no hands. Although she could ride a horse in fine style, she left the shooting of glass balls from horseback to Buffalo Bill. Annie concluded her act with a funny jig and would kick up her heels just before she left the arena. Once when a newspaper in England wondered how fast and accurate she was, she gave a special demonstration. Frank stood on a chair facing his wife’s back. At Annie’s command, he dropped a tin plate. Annie turned, fired and hit it square, all within about half a second.

Oakley with her Shotgun 1880s
Oakley was a young talent– only 15 when she won her contest with Frank Butler, and only 25 when she was signed on with Buffalo Bill. (Heritage Auctions)

Annie Oakley had a theatrical flair and the quickness and agility of an athlete. But none of it would have meant too much had she not been such a top hand with all kinds of firearms. She practiced constantly and did not rely on trickery; she was no sham shooting star. Among her favorite shotguns were a Lancaster and a Francotte, her favorite rifles included a Winchester and a Marlin, and she used Colts and Smith & Wesson handguns equally well. ‘Guns, rifles and pistols are of many styles,’ she once said, ‘and to declare that any one make is superior to all others would show a very narrow mind and limited knowledge of firearms….Nobody should trust their lives behind a cheap gun.’

The famous Sioux (Lakota) spiritual leader and medicine man Sitting Bull toured with the Wild West during the 1885 season. Annie had actually met him the previous year in a St. Paul, Minn., theater, when Sitting Bull, then a resident of the Standing Rock Reservation in Dakota Territory, watched her fire a rifle to snuff out a burning candle. Apparently, Sitting Bull was so impressed that afterward he asked to see the little white woman. Annie then gave Sitting Bull a picture of herself, while he gave her moccasins he had worn at the Battle of the Little Bighorn, as well as the nickname Watanya Cicilla (‘Little Sure Shot’). They were happily reunited the next year as employees of Cody’s Wild West. Whenever Sitting Bull got peevish that season, Cody would send for Little Sure Shot, who would talk to the Lakota leader for a while and then do her jig before leaving his quarters. That inevitably would make Sitting Bull laugh and would lift his spirits. But her presence was not enough to make him want to continue with the show another season.

In the spring of 1886, while the Wild West performed in Washington, D.C., en route to an extended summer stay at Erastina, on Staten Island, an insect lodged itself deep inside Annie Oakley’s ear. By June, she had an ear infection, but, against doctor’s orders, she still rode in the 17-mile opening-day parade in New York City. Near the end of it, she collapsed, and doctors determined that the area behind her eardrum needed to be lanced to drain its poison. The bedridden Li’l Missie missed four performances at Erastina (probably the only four she missed during her show career) before she hobbled into the arena on the fifth day to shoot again. She had plenty of grit for sure, but part of Annie Oakley’s motivation for getting back in action was the fact that Cody had hired a younger female shooter, Lillian Smith, for the 1886 season. At the time, Annie may have been concerned about her job security. But there was room for both of them, and the Wild West continued to be a big hit when it moved into Madison Square Garden that winter.

In 1887, the two women sharpshooters and the rest of Buffalo Bill’s Wild West sailed to London as part of the U.S. delegation to Queen Victoria’s Golden Jubilee. That May 5, Prince Albert Edward delighted in a special performance by the company and afterward wanted to meet the cast members. Annie Oakley had heard that women would flirt with the prince in front of his wife. When the prince was introduced to Annie and extended his hand, Annie passed it by and shook the princess’ hand first. She told the prince, ‘You’ll have to forgive me, I’m an American, and in America, women come first.’

On May 11, it was Queen Victoria’s turn to have a command performance. It was held at the exhibition grounds after her courtiers convinced her that they couldn’t fit Cody’s outfit into Windsor Castle. When the American flag entered the arena, Queen Victoria stood up and bowed deeply, and Cody’s company roared its approval. For the first time in history, an English monarch had saluted the Star-Spangled Banner. After Lillian Smith and Annie Oakley had curtsied and walked up to her, the queen told Annie, ‘You are a very clever little girl.’ L’il Missie had become an international star. At least one newspaper said that her marksmanship was better than that of Buffalo Bill.

Annie Oakley’s rising fame may have gone to her head, or to the head of her husband, and a rift developed between them and Cody. The couple left the Wild West. Annie did not explain the break from Cody, but she did say that the reasons she left were ‘too long to tell.’ She and Frank toured with vaudeville impresario Tony Pastor’s show in the spring of 1888. That summer, they hooked up with struggling Pawnee Bill (real name Gordon W. Lillie), a genuine frontiersman who had turned to showmanship, just like Buffalo Bill. Even though Pawnee Bill’s wife, May Lillie, was a sharpshooter with Pawnee Bill’s Wild West, Annie Oakley received top billing. Annie left the new show after a month to rejoin Pastor on a fall tour, and Pawnee Bill went broke less than three months later. While Annie was touring with Pastor, Frank Butler also arranged frequent shooting matches and exhibitions for his wife. In one match for $50 she broke all 50 clay birds, and in another, featuring 50 live pigeons, she defeated Miles Johnson, champion of New Jersey.

On Christmas Eve 1888, Annie Oakley made her debut as an actress in the Western melodrama Deadwood Dick. The play was not a success, and by early February 1889 the theater company had folded. One of the Deadwood Dick managers, though, was John Burke (who was a press agent for Buffalo Bill’s Wild West), and he was probably the one who convinced Frank Butler and Annie Oakley to rejoin Buffalo Bill for a spring run in Paris. That same year, Lillian Smith left the show, and Annie had no competition from any other female sharpshooter in France.

At first, the French apparently thought Buffalo Bill’s whole spectacle, including the shooting, was a fake, but when they saw Annie Oakley perform, they became convinced that she was the real thing. Nate Salsbury, Cody’s business partner, wrote that Annie Oakley saved the show. According to the scrapbooks at the Buffalo Bill Historical Center in Cody, Wyo., the French, like the rest of the world, idolized Little Sure Shot. The French papers also played up Cody’s reputation as a womanizer.

The Paris show ran until the fall of 1889, and then the Wild West ventured on an extended European tour. The English and Italians were most impressed by the horseback riding, but the Germans, especially Prussian military men, took a greater interest in the show’s logistics. The Germans were amazed by the Wild West’s efficient rail movement and the fact that Cody fed his crew three hot meals a day regardless of travel. After World War I started, Annie Oakley heard a rumor that the Germans modeled the movement of the German regiment after the movement of Buffalo Bill’s large company. When reporters reminded Li’l Missie that she had shot a cigarette out of the mouth of the kaiser (Wilhelm II) during the 1890-91 tour, she remarked that she wished that she had missed that particular shot. In Strassburg, Germany, in 1890, Cody sneaked into Annie Oakley’s tent and wrote in her autograph book: ‘To the loveliest and truest little woman, both in heart and aim, in all the world. Sworn by and before myself. W.F. Cody, Buffalo Bill.’

When Annie Oakley returned to the United States in October 1892, she was a celebrity who reportedly made more money than any other of Cody’s Wild West employees. In the fall of 1894, Buffalo Bill Cody, Annie Oakley and a handful of Indians performed in front of Thomas Edison’s moving-picture machine at the inventor’s laboratory near Orange Mountain in New Jersey. Edison was delighted that his machine could reproduce gun smoke and the shattering of glass balls. The public could go to kinetoscope parlors and, for a nickel, view these early Edison films in peep-show machines. Now, people didn’t have to see Annie Oakley live to know her. She had become the first ‘cowgirl’ in motion pictures.

Oakley Firing Revolver 1892
Though best known for her shotgun skills, Oakley was proficient with all kinds of firearms. Here, she shows off her trademark Smith & Wesson alongside a fellow Wild West performer in England, 1892. (Denver Public Library)

Meanwhile the show went on, and it became more of a road show than ever. Buffalo Bill’s Wild West played in more than 130 towns in both 1895 and 1896. In 1897, the Wild West played in Canada for the first time since Sitting Bull was a headliner in 1885. Annie admitted in 1899 that she had begun to at least think about retirement. The railroad travel was endless, and it had its dangers. Train accidents were not uncommon.

One notable wreck occurred at 3 a.m. on October 29, 1901, near Lindwood, N.C., while the company was headed to Danville, Va., for its last performance of the season. When the first section passed the switching station, the switcher thought that it was the whole outfit, so he threw the switch. The second section ran into an oncoming train. The wooden cars became so many piles of kindling as people and animals cried out in pain and steam hissed. Legend says that Annie Oakley, now 41, was found pinned beneath the rubble and it took several hours before she could be extracted. As Li’l Missie was carried by stretcher past some wounded horses that had to be shot, she supposedly remarked that she felt sorry for them. Just 17 hours after the wreck, according to legend, her brown hair turned totally white because of the horror of the accident.

Biographer Shirl Kasper, however, argues that Annie was not badly hurt in the wreck (the Charlotte Observer reported that nobody from the Wild West was injured) and that while Annie’s hair did turn white rather fast, it wasn’t because of the train wreck. Two newspaper articles in Annie’s scrapbooks at the Buffalo Bill Historical Center say that her hair turned white after she sat too long in a hot bath at a health resort later that year. In any case, says Kasper, it was her white hair, not any bodily injuries, that convinced Annie Oakley to immediately leave Buffalo Bill’s Wild West.

After her retirement from the Wild West, Annie Oakley tried her hand at acting again, appearing as the lead in a play called The Western Girl, which opened in New Jersey in November 1902. She looked much as she had while shooting in the Wild West, except now she wore a brown wig to hide her white hair. She also would teach shooting at exclusive clubs. Meanwhile, her husband worked for the Union Metallic Cartridge Company, promoting its products to the growing number of trapshooters. In the spring of 1910, Frank and Annie attended a Wild West show at Madison Square Garden known as the ‘Two Bills Show,’ because Buffalo Bill’s outfit had merged with Pawnee Bill’s outfit. Cody apparently asked Annie to rejoin the show, but she and Frank turned the old showman down. Instead, the following year, they joined up with Vernon C. Seavers’ Young Buffalo Wild West, and Little Sure Shot continued to shoot for that outfit until retiring for good in 1913. Annie and Frank continued to be friends with Cody, though, and when Buffalo Bill died on January 10, 1917, she wrote a glowing eulogy.

After giving her last performance with Young Buffalo Wild West on October 4, 1913, Annie and Frank retired to a new home in Cambridge, Md., and also spent a lot of their time at resorts in Pinehurst, N.C., and Leesburg, Fla. Hunting and shooting remained a big part of their lives. They had no children. In the summer of 1922, when she was about to turn 62, Annie Oakley performed at a benefit show on Long Island (a clip of her performance that day can be seen at the Buffalo Bill Historical Center). The New York Herald hinted that she might be making a comeback in show biz and could appear in the movies soon. It never happened. That November, she fractured her hip and an ankle in a car accident in Florida. The steel leg brace she was forced to wear did not, however, keep her from resuming her shooting and hunting.

Annie Oakley was back home in Darke County, Ohio, when she died on November 3, 1926. She had never fully recovered from the car accident. The doctor wrote ‘pernicious anemia’ as her cause of death. Frank Butler reportedly stopped eating or caring. Less than three weeks later, on November 21, he seemed to fulfill his wish by joining his beloved wife in death.

Annie Oakley had not been born in the West, and she had not lived there. But for many years she had certainly looked like a cowgirl, and she had ridden a horse and shot better than most any Westerner, of either sex, while performing in Wild West shows. To call her, then, a ‘Western legend’ does not miss the mark…even if she was too good, and too good a shot, to shoot anyone.

This article was written by Eric V. Sorg and originally appeared in the February 2001 issue of Wild West.