New York is a crazy place, filled with some crazy people. It's why we love it so much. One of the better stories is that of Tommy Fitzpatrick, from which our Fitz frame got its name.
The story starts on September 30th, 1956 around 3 AM. After a long night of drinking up in Washington Heights, Tommy, 26 at the time, decided to make a bar bet - He could land a plane on a New York City street. A man of his word, he stole a plane from the Teterboro School of Aeronautics in New Jersey, flew it to the city, and landed it on St. Nicholas Avenue near 191st Street - outside of the bar he had been drinking in. Tommy was arrested, but the owner of the plane never pressed charges, and New York Times reported it as a "feat of aeronautics."
Two years later, on October 4th, 1958 Tommy pulled the stunt again. The story goes that he told his story to someone at a bar, and they didn't believe him. Naturally, he had to prove them wrong...He stole another plane from the same airport, and this time landed it on Amsterdam and 187th Street.
You can read the New York Times account here.