Sky Kings and Daredevils: Aerialists Who Thrilled the Great Lakes Region

Ivan Unger and Gladys Roy play tennis on top of a biplane in 1925.

Long before commercial air travel became routine, a daring class of performers turned the sky itself into their stage. From the late 1800s through the 1930s, wingwalkers, parachutists, and balloonists brought heart-pounding thrills to Midwestern skies. They appeared at county fairs, lake resorts, and small-town celebrations, walking along wings of biplanes, leaping from hot-air balloons, or drifting back to Earth beneath patchwork parachutes. Equal parts aviation pioneers and showbiz daredevils, these skybound performers embodied the spirit of the Golden Age — fearless, innovative, and ready to risk everything for applause.

The Age of Daredevils Begins

These airborne entertainers weren’t just sideshow spectacles — they were often the main attraction. As the Midwest boomed with county fairs, industrial expos, and beachside amusement parks, promoters knew nothing drew a crowd like someone risking their life above it. Crowds packed into fields and fairgrounds, craning their necks skyward, shielding their eyes from the sun as tiny silhouettes balanced on wings, leapt from balloons, or floated earthward in graceful silence. Each performer brought their own signature style, but all shared a common goal: to astonish audiences and push the limits of flight. Let’s meet some of the sky’s most fearless showmen and showwomen.

A balloon ascends before a crowd during an exhibition at the 1905 St. Louis World’s Fair. Balloon ascensions like this were major attractions at fairs and expos across the Midwest in the early 20th century.

Before the Plane, There Was the Parachute

Long before propellers roared and wingwalkers danced above the clouds, balloonists and parachutists were already turning the sky into a spectacle. From the mid-1800s through the early 1900s, these airborne pioneers ascended in gas balloons and hot-air contraptions, performing gravity-defying stunts that captivated fairgoers across the Midwest. As the crowd held its breath, a tiny figure would leap from the basket high overhead, drifting earthward beneath a silk parachute — or sometimes with nothing but a prayer and a modified umbrella. These early aeronauts paved the way for future aviation daredevils, proving that the sky wasn't just for birds — it could be a stage.

One of the most celebrated figures of the era was Professor Thomas S. Baldwin, often referred to as “Captain” Baldwin. A Civil War veteran turned balloonist, he pioneered balloon-parachute acts that stunned audiences in Detroit, St. Louis, and beyond. Later, he would help design early dirigibles and powered aircraft, bridging the gap between lighter-than-air and heavier-than-air flight.

Baldwin also trained and toured with aeronaut troupes, often billed as Captain Baldwin’s Aeronauts, who traveled the Midwest putting on dramatic aerial shows. Fairgoers from Milwaukee to St. Louis would gather for these thrilling exhibitions, which typically ended with a parachute drop and a cheer from the crowd.

One of the boldest stars to emerge from this world was Georgia “Tiny” Broadwick, a young woman from North Carolina who became the first woman to parachute from an airplane. In the 1910s, she toured throughout the Midwest, leaping from planes over racetracks and fairgrounds. Her small stature and immense courage made her a crowd favorite wherever she appeared.

Lincoln Beachey, who later gained fame as a powered flight daredevil, got his start in ballooning. Before mastering loops and dives in an airplane, Beachey performed dramatic balloon ascents and parachute jumps at events in Cleveland, Cincinnati, Chicago, and other major cities. His transition from balloonist to aviator reflected the larger shift in public fascination—from the stately float of a balloon to the roaring speed of early aircraft.

These early daredevils laid the groundwork for the barnstormers and wing-walkers who followed. They brought wonder to the skies and gave Midwestern audiences a first taste of what it meant to fly.

Bessie Coleman stands proudly on the wing of her biplane in the 1920s. As the first African American woman to earn a pilot’s license, she dazzled crowds with daring flight exhibitions across the Midwest.

Wingwalkers & Aerial Daredevils

In the early decades of the 20th century, nothing thrilled a crowd quite like the sight of a human clinging to the wing of a flying biplane—or leaping from one midair aircraft to another. These daredevils pushed the limits of aviation and became folk heroes in towns across the Midwest. Barnstorming troupes crisscrossed the region, making stops at county fairs, racetracks, and temporary airfields carved out of cornfields. For many Midwesterners, this was their first encounter with flight—and it came with gasps, cheers, and the ever-present possibility of danger.

Ormer Locklear was one of the first national celebrities in this new airborne art. A former Army flight instructor, Locklear dazzled audiences with his fearless wing-walking routines. He performed stunts above Chicago, Dayton, and other Midwestern cities before tragically dying in a nighttime film stunt in 1920.

Lillian Boyer, a waitress-turned-aerialist from Nebraska, took her first airplane ride in 1921—and was wing-walking by her second. Over the next eight years, she performed over 350 stunts, including midair transfers from moving cars to airplanes. She thrilled fairgoers in Indiana, Illinois, and Ohio, becoming one of the few women to dominate this male-dominated arena.

Gladys Ingle, a standout performer with the stunt group 13 Black Cats, became famous for midair plane-to-plane transfers and inflight maintenance (like replacing landing gear while airborne!). She brought her daring act to air shows in Michigan and Illinois, inspiring awe wherever she flew.

Ivan Unger and Gladys Roy pushed spectacle to the limit by performing choreographed stunts—most famously, a staged tennis match—on the wings of a flying aircraft. Their dramatic tours brought them to major Midwest cities like Minneapolis and Cleveland, drawing headlines and huge crowds.

Bessie Coleman, the first African American woman to earn a pilot’s license, captivated crowds across the Midwest with her breathtaking loops, dives, and controlled spins. From Chicago exhibitions to barnstorming events in Indiana, she became a beloved figure in the region before her untimely death during a practice flight in 1926.

Ruth Law, a pioneer even before World War I, flew her way into history with bold long-distance flights and high-profile performances. Her famous Chicago-to-New York flight in 1916 shattered records and helped legitimize women in aviation. She continued touring through Midwest airfields, inspiring a generation of young fans.

Georgia “Tiny” Broadwick prepares for a parachute jump from a Martin T biplane piloted by aviation pioneer Glenn Martin, c. 1914. Broadwick, known as the “First Lady of Parachuting,” made history with jumps that helped shape early military aviation practices.

Capturing the Era’s Spirit

Though the age of aerial daredevils has largely faded into history, their spirit still soars. Wingwalkers, parachutists, and balloonists were thrill-seeking entertainers, but they were also innovators and pioneers who brought the marvel of flight to everyday Americans. In towns where most people had never seen a plane up close, they turned the sky into a theater of dreams.

These daredevils symbolized the boldness of the early 20th century — a time when Americans celebrated innovation, risk-taking, and the conquest of the skies. Their performances reflected a nation newly-obsessed with speed, flight, and adventure.

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