In the 1920s, Waldo Pepper is a down-on-his luck former World War I pilot who gets by on making barnstorming appearances, giving rides and doing stunts... all of which are getting harder to hold the public's attention with, as airplanes are becoming more common.
Waldo also feels cheated by the fact that he never got to fly against the greatest of German aces, Ernst Kessler. When a series of disastrous mishaps derails his life, it puts him in a place to not only meet the famed ace, but test his flying skills.
This film contains examples of:
- Ace Pilot: Most of the main characters, but Ernst Kessler is the one that everyone keeps trying to match.
- Bystander Syndrome: After Ezra crashes, and especially after the wreck catches fire, the gathered crowd just stands around and watches as Waldo tries to pull him out by himself.
- Buzzing the Deck: Kessler starts his air performance with an upside down low pass that causes the announcer to fall over. Later after Ezra crashes, Waldo, furious at the crowds who came to gawk but did nothing to help, gets in a plane and starts buzzing them to drive them away from the wreckage.
- California Doubling: In-Universe, as they're filming a movie about air battle of World War I over France, but the filming's being done in California.
- Cerebus Syndrome: Most of the film is a fairly light-hearted account of barnstorming pilots during the 1920s until Mary Beth falls off a plane during a failed wing-walking stunt. After that, it's one tragic incident after another.
- When it was released, The Great Waldo Pepper was considered a box office disappointment. The screenwriter of the film, William Goldman, later admitted the wing-walking scene was the point in the movie where they lost the audience.
- Do a Barrel Roll: Ezra is killed attempting to perform the world's first outside loop, triggering the psychotic episode that costs Waldo his pilot's license.
- Duel to the Death: Waldo and Kessler turn what is supposed to be a filming flight into one.
- End of an Age: By the end of the movie, Waldo and Kessler realize the era of barmstorming—and their way of life—is all but over.
- Just Plane Wrong: Two relatively common Tiger Moth biplanes were wrecked in the crash scenes, standing in for the much rarer Standard J-1. Ironically, most sources about the film mistakenly identify the Standard J-1s actually used in the movie as the smaller (but more famous) Curtis JN-4 "Jenny". Tallmantz aviation, like most real Barnstormers, preferred the Standard because it was larger, stronger, and used a more reliable engine.
- Ramming Always Works: Since they don't have live ammunition, Waldo and Kessler duke it out with the planes themselves.
- The Roaring '20s: The barnstorming era, specifically.
- Take My Hand: Averted when Waldo tells Mary Beth to take his hand while trying to coax her off an airplane wing after she freezes in panic during a midair wing-walking stunt. Unfortunately she lets go of the strut she's clinging to and lunges at Waldo with BOTH hands. He can't catch her and she falls to her death.
- Worthy Opponent: Kessler saw Madden this way, and eventually comes to see Waldo as one as well.
- Wronski Feint: Attempted by Kessler when he tries to force Waldo into the ground at the end.