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My father was in a bar back in Washington Heights, NYC back in the fifties. Some drunk guy in the bar insisted he was a pilot, but they all just kept scoffing at him, so the guy left furious.

A few hours later, at 3 in the morning, he walked back in the bar and told him he had proof. They went outside and he showed them the plane he had just landed outside the bar on St. Nicholas avenue. He had taken a bus to Teterboro NJ, stole a plane, and landed it on a street in Manhattan, just to prove a point.

He was arrested immediately.

BIG CROWD OUT TO SEE THOMAS'S WIND WAGON
The Doctor Was Ready to Take a Run or a Flight. BUT SOMETHING BROKE AGAIN Visitors Inspect the Helecoptere, a Unique Auto That Is to Start an Aeroplane Soaring.
New York Times (1857-Current file). New York, N.Y.: Dec 8, 1906. pg. 6, 1 pgs

Dr. Julian P. Thomas's helecoptere did not get into action yesterday, though Dr. Thomas announced in the morning that he would take a run, or a flight, or whatever the experiment with his new and unique machine might turn out to be. The trial may be made to-day.

Not Dr. Thomas, but here's a contemporaneous attempt at the windwagon from France...

Thomas next ran his Wind Wagon up Broadway from 67th to 71st Streets...

THE WIND WAGON GOES; MIGHT USE IT IN ARCTIC
Dr. Thomas Spins Down Broadway in His Helecoptere. HOPES TO FLY WITH IT NEXT The Machine May Run or Sail or Fly Over All Obstacles to the Pole.
New York Times (1857-Current file). New York, N.Y.: Dec 10, 1906. pg. 1, 1 pgs

Dr. Julian P. Thomas's new wind wagon, which he terms a helecoptere, made a trip yesterday afternoon along upper Broadway, to the wonderment of a thousand bystanders and to the complete satisfaction of the inventor, who hopes that eventually he will be able to get a running start for an aeroplane with the new contrivance.

This last trip he was chased by bicycle policeman Dobbins, who caught up to him when the machine stopped at 71st St. When Dobbins demanded to see his license, Dr. Thomas replied that he had none.
"Well, you ought to have one."
"What'll I ask for. I don't konow what sort of a machine this is yet."

And here's another Manhattan flight attempt, by the great WestSide aviator, Charles K. Hamilton, who was dragged into the air by an automobile of a friend of the kite's inventor, Isreal Ludlow:

That's 1905. For their next attempts they took it to the Hudson River, and pulled Hamilton by motorboat.

From Early Automobiles and Airplanes: The Cultural Lag