Annie Oakley was the first American female superstar, and a real exemplary version of the American Dream. Born 1860 in a rural area of Ohio, she was given away by her mother after her father died at age 9 along with her sister to work at an orphanage as she couldn’t afford to keep her and was “adopted” by an evil family that put her through an almost indentured slavery, before she escaped after two years, returning to the orphanage. She eventually went back to her original family, and to help pay for food and mortgage, mastered shooting small game cleanly to sell to restaurants and hotels, eventually earning a great reputation. When she was put up to a shooting competition with Frank Butler, a top shooter and vaudeville performer, she beat Frank, who quickly fell in love with her, and realizing that she was better than he, made her the head of their act. In 1884 she met Native American leader Sitting Bull, who was so impressed with her and her abilities, that he “adopted” her as his daughter and they joined Buffalo Bill’s Wild West Show in 1885, where she quickly became a headliner. Audiences couldn’t get enough of her, as she could shoot the tip of a cigarette held in her husband’s lips, hit the thin edge of a playing card from 30 paces and shoot distant targets while looking in a mirror and more. When the Wild West Show traveled Europe, Annie was a sensation, and got to meet Queen Victoria and shot a cigarette out of Kaiser Wilhelm II’s mouth. She eventually left (and came back) to the Wild West Show, but continued to perform, being a top earner for the Wild West she shared her money with her extended family and gave donations to orphan charities, and during WWI volunteered to organize a regiment of female sharpshooters, but after her petition was ignored, helped to raise money for the Red Cross with exhibition work at army camps.

She was slandered by Hearst’s publications, Oakley spent six years winning 54 of 55 libel lawsuits against his newspapers, which begat laws to prevent yellow journalism that still stand today. After a debilitating automobile accident that forced her to wear a steel brace on her right leg, she recovered to perform and set more records, and held classes for teaching women to shoot for free. After her death at age 66 in 1926 from pernicious anemia in Ohio, her husband Frank was so grieved that he stopped eating and died 18 days later. After her death it was discovered, she had given her entire fortune away to her extended family and to charity.

It was amazing painting this portrait of this incredible woman. I always advocate, especially with my cartooning students, for “strong female protagonists,” and Annie was certainly that—way before Lady Gaga and Madonna she was internationally known as not only the best sharpshooter of her day (when shooting was a way of life for many), but as a kind, smart (and self-educated), and super-strong woman, in a loving relationship with a husband who easily let her take the driving seat in their marriage and in their acclaimed act. When painting from photos, I feel it’s my job to make it “better” than the photo, and how it’s “not like the photo” is ultimately what is “me” about it. In these old photos, which were made into postcards to sell at the shows and beyond, they are in the studio shots, with painted backgrounds. When I’m painting, I always listen to music and audiobooks, etc., to help me get to know the person even more, and like a method actor, to get inside the character and relate to it to help it come “alive.” For Annie, I listened of course to her famous biography written by her friend stage comedian Fred Stone, in addition to versions of the musical (even the Ethel Merman was really a fiction based very loosely on fact), and a lot of country music that she might have enjoyed if she had lived to hear it (Dolly Parton was especially good). I found the Carter Family, the famous foundation of much of country music (and folk) worked the best, as they recorded many traditional songs that existed in Annie’s time, much of it religious music (and Annie was religious).

I hope I did justice to her bearing and her legacy—it was interesting to bring color to the sepia-toned image, and imagine, interpreting the painting behind her to be as “real” as possible, the other worlds that it could depict, both the forests her rural upbringing, but also a “cabin in the sky” where hopefully her spirit resides today!