Willie Nelson, 41 --- Where and when: Dallas,1974 Arrested for: Possession of marijuana. Outcome: The legendary cannabis connoisseur avoided jail time—and went on to be arrested again. The last time, in 2011, the prosecutor said he'd let him off if Nelson would pay a small fine and, as community service, sing “Blue Eyes Smiling in the Rain.” (It was a joke—Nelson was released without having to perform.)