Thomas Fitzpatrick

After a barroom bet, Thomas Fitzpatrick stole a plane from a New Jersey airport and landed it on a Manhattan street in front of the bar in 1956. He did it again 2 years later when someone refused to believe him. – WTF Fun Facts

Source: https://web.archive.org/web/20200422085235/https://cityroom.blogs.nytimes.com/2013/06/04/long-ago-a-pilot-landed-on-an-uptown-street-thats-where-the-bar-was/