Check out this great article from the NY Times that came out today. It's about a Harlem bar bet in 1951 that resulted in a 26 y/o stealing a plane in New Jersey to landing it on the streets of NYC... drunk.... at 3am (it was really dark in 1958). Six years later he did it again because a patron at the same bar didn't believe he did it the first time.
Have an audacious story of your own? Share it (or links to it) in the comments.