If Robert Redford is the best model of the American Dream in all its smiling, handsome glory (and I think he is), then he must also be its most effective destroyer. Through characters like the Sundance Kid (Butch Cassidy and the Sundance Kid) and Jay Gatsby (The Great Gatsby) who turn themselves into legends, and Bob Woodward (All the President’s Men) who turns politicians into criminals, Redford has made his career a mission to demystify the neatly packaged illusion of American exceptionalism. Yet I don’t think either of those crushes The Dream as brutally as The Great Waldo Pepper does, leaving it burning in the wreckage of a monoplane. And that’s saying something for a movie as lighthearted as this one.
It’s 1926 in down-home Nebraska, and all that’s left of World War I are the daredevil pilots who duke it out in barnstorming competitions right over our heads. Simple Midwesterners search the skies at the sound of a biplane engine while J.P. Sousa-style marches signal the arrival of our hero, Waldo Pepper. There’s only one problem–Pepper is a liar and a cheat. He never fought against the notorious Ernst Kessler in the war (he didn’t fight at all on account of his being a flight instructor), but he’ll say he did if it gets him an easy buck (on account of his being poor and desperate). But despite being a great storyteller and showman, Pepper is actually the real deal. He’s “Great,” not because he’s got money like Gatsby, but because his flying skills are (nearly) unmatched (that pesky Kessler is still alive after all). In this day and age, though, where almost every man and his grand-pappy seems to have a plane, Pepper’s gotta find a way to stand out.
With the help of a struggling flying circus, Pepper tries new death-defying stunts and a newfangled monoplane in the hopes of outdoing Kessler and the competition. But amid the joyous montages and hilarious slapstick, the movie that I thought would cheer me up turns into a tragedy. “It Girl of the Sky” Mary Beth (Susan Sarandon) falls to her death during a stunt gone wrong, and engineer Ezra crashes and burns his revolutionary monoplane. There’s no ominous music to warn you, nor any drawn out Peter Jackson-style close-ups to milk the moment. Only sudden shock and silent confusion. It’s the 70s, when movies are the business of realism, no matter how much it hurts.
And how realistic! Director George Roy Hill, a former WWII pilot himself, captures the flight sequences so dizzyingly that at times they’re literally nauseating. He even had actors Robert Redford and Bo Svenson perform without harnesses or parachutes because we really need them to fear for their lives for us to get the full effect.

That Pepper goes to such lengths for his craft proves his passion. Watching him shuffle across the wing thousands of feet in the air, we just wish he’d prove it by writing a song or something. From the outside, it’s easy to think he’s a maniac. That is until he heads to Hollywood, the land of dreams, looking for a job as a stunt pilot on a film.
That film happens to be about WWI, and Kessler happens to be a consultant, and Pepper just so happens to know a lot about the story. But the director waves it off, saying, “Anybody can provide accuracy. But only artists can supply truth.” It’s the grand, sweeping stuff of Oscar speeches and director roundtables, and for the first time Pepper is on the other side of someone’s dramatized retelling of a story he loves. He realizes that accuracy is everything. Accuracy keeps you alive when you’re at war or standing at the end of a wing for people’s amusement. Redford smiles and keeps his cool, but we’ve seen how he can get when friends die on the job and it’s scary (it involves chasing people with a plane).
So as Kessler and Pepper go up in their planes to shoot the scene, we start to understand what made them leave the parachutes behind. They’ve come too far without them to give into health and safety protocols now. Only they understand what it means to put one’s life on the line for the American Dream and they’re done with peddling illusions. Pepper and Redford have faked a lot of things in their lives, but cheating death is not one of them.
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