The Great Waldo Pepper (1975) on Netflix

Waldo Pepper was a World War I flight trainer. Waldo believes the honor of the best WWI fighter pilot goes to German Ernst Kessler, although Waldo's flight commander Newt believes that if Waldo had entered the war earlier and had got the flight time, he would have proved himself to be the best. In the post-war era, Waldo, self-coined as the "Great Waldo Pepper", has like many war pilots resorted to barnstorming to make a living. Instead of the penny-ante flights he provides to adoring fans, Waldo wants to join Dillhoefer's flying circus. Dillhoefer will only let him join if he can prove he can perform a death defying feat that his audiences crave to see. He decides to join forces with sometimes rival pilot, Axel Olsson, to come up with such a stunt. Another possibility, with the help of plane designer Ezra Stiles, his girlfriend Maude's brother, is to complete the first ever outside loop. But when the defying part of death defying comes close to not happening, Waldo's livelihood is jeopardized. He may have to reinvent himself if that livelihood is no longer a possibility. An unexpected source may allow Waldo to show if he really was and is the greatest.