Paul McCartney

The former Beatle may be a knight, but Sir Paul once lived a true rock star lifestyle. He was caught smuggling half a pound of marijuana through the Tokyo airport in 1980. "When the fellow pulled it out of the suitcase, he looked more embarrassed than me," McCartney remembered. "I think he just wanted to put it back in and forget the whole thing, you know, but there it was." The singer spent 10 days in jail and had to cancel 11 concerts, forcing him to pay out £1 million. But he was lucky to avoid the usual sentence under Japanese law: seven years of hard labor. McCartney was caught with marijuana again during a 1984 trip to Barbados, but was only fined $200 for that mistake.