For as long as birds have graced the skies, man has dreamt of flying. Limited only by imagination, inventions originated with gliders and balloons. The first man to achieve flight lifted to the skies in a Montgolfier-designed hot air balloon in 1783. As early as the 9th century, Arabic inventor and renaissance man Abbas ibn Firnas tried to fly with wings made of real feathers. A contemporary poet chronicled his attempt writing, “He surpassed in velocity the flight of the ostrich, but he neglected to arm his body with the strength of the vulture.”

The crash-landing injured his back, but he may have inspired the glider. The aspiration for flight has brought us many failures and crash landings, but it’s also taken man to the moon. Here we look at the best of the worst in-flight innovation, starting with the Wright brothers.

In 1903, The Wright Flyer completed the first airplane flight. 120 years after balloon aviation, Orville Wright piloted his craft for a miraculous 59 seconds. That’s right, his flyer traversed 852 feet over the beaches of Kitty Hawk, North Carolina in just under a minute. It was one of several attempts that day by Orville and his brother Wilbur Wright. The last landing was so turbulent it broke the craft’s front supports. Soon after, a swift wind tumbled the Wright Flyer into somersaults. The damage prevented it from ever being flown again. It may seem like a failure, but it ushered in the age of aviation and the invention of the modern airplane as we know it today.

Years later, Orville Wright was demonstrating a different craft to the U.S. Army. With a man in the passenger seat, Orville was trying to navigate the landing when a propeller fell off the plane. The resulting plunge killed the passenger. Another first. In 1908, Lieutenant Thomas Selfridge became the first man to die by airplane crash. Wright survived, but he had to be hospitalized for a week.