The '50s were a different time. A time of poodle skirts and sock hops. A time of rock and roll and malt shops. A time, apparently, when a man could land a plane in a narrow street in Manhattan and walk away with nothing but a $100 fine.

It was September 30, 1956, and Thomas Fitzpatrick, a.k.a. Tommy Fitz, had been out drinking with friends. Sometime in the wee hours of the morning, presumably after enjoying a few adult beverages, Fitzpatrick bet his buddies he could get to New Jersey and back in just 15 minutes. Impossible, you say? So did his buddies. But Fitzpatrick had a hidden advantage: His pilot’s license. After disappearing into the night, he returned to 191st Street and St. Nicholas Avenue in Washington Heights, piloting a single-engine plane he had “borrowed” from the Teterboro School of Aeronautics in New Jersey. When originally questioned, Fitz told police he had engine trouble and had to make an emergency landing. Though he was originally jailed with bail set at $5,000, the prankster ended up getting off with just a $100 fine.

Once would have been enough for most people. But Tommy Fitz was not most people. Two years later, the pilot was recounting his tale, but his “unidentified drinking friend” refused to believe him. Once again, Fitzpatrick disappeared, only to return a short while later in a plane. This time he parked it at 187th Street and Amsterdam Avenue. Police recognized Fitzpatrick’s signature move and were able to apprehend him quickly; this time, he spent six months in jail. “It’s the lousy drink,” Fitz later admitted.

[h/t The New York Times