Love and Legend: The Story of Annie Oakley

Howdy. Chip Schweiger, here. 

Welcome to another edition of Way Out West. 

The podcast that takes you on a journey through the stories of the American West, brings you the very best cowboy wisdom, and celebrates the cowboys and cowgirls—who are feeding a nation. 

Out here on the open prairie, where the sunsets stretch forever and the wind whispers old secrets through the grass, legends are born from more than just grit and gunpowder. Sometimes, it’s love—unexpected and wild as a mustang—that shapes the stories we remember most.

Let’s ride back to a time when the American West was still untamed. In the heart of that wild country, a sharpshooter named Annie Oakley met her match—not just at the end of a rifle barrel, but in the eyes of a fellow marksman, Frank Butler. Their story isn’t just about daring shots and show business glitz; it’s a story of partnership, devotion, and the kind of romance that could only happen way out west.

After the episode, check out the show notes at WayOutWestPod.com/Annie-Oakley

[Short Music Break]

Welcome back.

Today, we’re zeroing in on one of the most legendary sharpshooters ever to grace the Wild West—Annie Oakley. 

Now, before we jump in, I want to share why Annie Oakley’s story has always resonated with me. Out here in the West, we talk a lot about grit, determination, and standing tall no matter the odds. 

 Annie Oakley is the perfect example of all that. Her journey from humble beginnings to becoming a legend reminds me that no matter where you start, it’s your spirit and hard work that make all the difference. That’s the kind of story I love sharing—because it’s what the cowboy way is all about.

So, let’s ride through the life and times of a woman who could outshoot, outsmart, and outshine just about anyone.

Chapter 1 - Early Life 

Let’s set the stage: It’s the late 1800s. The West is wild, full of promise and peril in equal measure. America is growing fast, and so are its legends. But for Annie Oakley—born Phoebe Ann Mosey in 1860—life started with more hardship than heroics.

She was born in a humble log cabin in Darke County, Ohio, the sixth of seven children. Her father, a Civil War veteran, died of pneumonia when Annie was just six, leaving the family in poverty. Her mother struggled to keep everyone fed and clothed, and young Annie learned early that if she wanted something, she’d have to work for it. And work she did.

Chapter 2 - A Young Crack Shot

By age eight, Annie was trapping, shooting, and hunting game to help put food on the table. She was so good with a rifle that she started selling game to local grocers and restaurants. Folks said she could shoot the head off a quail at 50 paces. In fact, by the time she was a teenager, she’d paid off her mother’s mortgage with her hunting earnings alone. That’s grit, right there.

But Annie’s childhood wasn’t just about hard work. She faced some real heartbreak, too. After her father’s death, she was sent to the “poor farm”—a kind of workhouse for orphans and destitute families. There, she endured harsh conditions and even abuse from the family she was sent to work for. But even in those tough times, her spirit never broke. She later said those years only made her stronger and more determined.

Chapter 3 - Enter Frank Butler

Now, let’s fast forward to 1875. Annie’s back home, and her reputation as a sharpshooter is growing. Enter Frank Butler, a professional marksman traveling the country, challenging locals to shooting matches. Frank was good—real good. But when he came to Ohio, he met his match. The locals set up a contest between Frank and the best shot in town. Imagine his surprise when that “best shot” turned out to be a petite, 15-year-old girl.

The contest was close, but Annie edged him out by a single shot. Frank was smitten—not just by her shooting, but by her spirit. The two struck up a friendship, which quickly blossomed into romance. They married the following year, and Annie joined Frank’s act. Before long, she was the star of the show.

Chapter 4 - Buffalo Bill's Wild West Show

Annie Oakley wasn’t just a trick shooter—she was a showstopper. She could split a playing card edgewise, shoot the ashes off a cigarette, and hit a dime tossed in the air—all with style and grace. She was a natural performer, with a quiet confidence that won over audiences everywhere.

Her big break came in 1885, when she and Frank joined Buffalo Bill’s Wild West show. This was the biggest show of its kind, traveling across America and even to Europe. Annie became the star attraction, performing for crowds of thousands and even royalty. She wowed Queen Victoria, stunned the Prince of Wales, and famously shot the ashes off a cigarette held by Germany’s Kaiser Wilhelm II. (And folks sometimes joke that maybe she should’ve missed that one, considering how history turned out!)

Chapter 5 - Fiercely Independent, Deeply Compassionate

What set Annie apart wasn’t just her skill—it was her character. She was fiercely independent, but also deeply compassionate. She donated much of her earnings to orphanages and veterans’ causes, remembering her own rough start in life. And she was a champion for women, teaching over 15,000 women how to shoot throughout her career. She believed that a woman who could handle a gun was a woman who could protect herself and her family—a radical idea at the time.

 Annie’s fame grew, but she never let it go to her head. She remained humble, signing autographs with a simple “Annie Oakley, Little Sure Shot”—a nickname given to her by Sitting Bull, the famous Lakota chief, who became one of her biggest fans and friends.

Chapter 6 - Did You Know?

Let’s pause for a “Did You Know?” segment:

• Annie Oakley was only five feet tall, but her presence filled any stage.
• She could shoot a playing card edgewise at 30 paces—and once did it 25 times in a row.
• She kept her own guns meticulously clean and often made her own costumes, favoring practical, modest outfits over flashy showgirl attire.
• Annie wasn’t just a performer—she was an advocate for safe gun handling and even designed her own shooting targets for practice and training.
• Annie adopted the stage name “Oakley” from the nearby town of Oakley, Ohio. She wanted a name that sounded strong and memorable—and it stuck.
• Many of Annie’s guns are now museum pieces, displayed in places like the National Cowgirl Museum and Hall of Fame in Fort Worth, Texas. Some are still privately owned by collectors, treasured as pieces of American history.

Chapter 7 - A Loving, Respectful Marriage

Now, let’s talk about Annie’s partnership with Frank Butler. Their marriage was a true partnership—Frank often stepped back, letting Annie take the spotlight. He managed the business side of things and supported her career, a rare dynamic at the time. They were married for over 50 years, and by all accounts, theirs was a loving, respectful relationship.

Annie’s career wasn’t without controversy. She faced her share of critics and even survived a smear campaign by a major newspaper, which falsely accused her of theft. Annie fought back, suing newspapers for libel—and won every case. Her reputation for honesty and integrity remained intact.

Chapter 8 - A Lasting Legacy

As the Wild West era faded, so did the big shows. But Annie kept performing, teaching, and advocating for women’s rights. She was injured in a train accident in 1901, but even that didn’t stop her—she recovered and returned to the stage, still hitting her mark every time.

Annie Oakley passed away in 1926, just 18 days before her beloved Frank. Some say he died of a broken heart. Together, they left behind a legacy of courage, kindness, and true Western spirit.

So, what can we learn from Annie Oakley’s story? She showed us that courage comes in all shapes and sizes, that perseverance pays off, and that you don’t have to be born into privilege to make your mark on the world. She was a trailblazer, a teacher, and a true legend of the American West.

Chapter 9 - Buster The Bull and the Cowboy Glossary Term of the Week

OK, before we wrap up for this week, we’ve got one more thing.

[BULL SOUND]

Yep, that distinctive call from Buster the Bull means it’s time for the cowboy glossary term of the week. 

And this week’s term is “Sure Shot” A “sure shot” is someone with exceptional marksmanship—a person you can count on to hit their target, no matter the distance or the challenge. In cowboy circles, being called a “sure shot” is high praise, and Annie Oakley herself was famously nicknamed “Little Sure Shot” by none other than Sitting Bull.

Chapter 10 - Thanks for Listening

Well, that’s a wrap on this week’s episode. Thanks for riding along with me today, folks. If you’re enjoying the show, be sure to subscribe and share it with a friend who loves a good Western yarn. 

And don’t forget to check out my blog at CowboyAccountant.com for more stories and insights from out here, Way Out West.

This is Chip Schweiger, reminding you to keep your powder dry and your spirits high.

We’ll see y’all down the road.