2. Paul McCartney*
Although he has been arrested multiple times over his life, one incident in particular stands out.
In 1980, McCartney was arrested and sentenced to 10 days in prison for attempting to take a ½ pound of marijuana through the Tokyo airport.
Even though airport security has come up leaps and bounds since the 80’s, one still has to struggle to imagine how Sir Paul McCartney thought it was a good idea to try to go through an airport with so much of an illegal substance with him. Rockstars, right?