2 Live Crew

On March 2, 1990, 2 Live Crew's As Nasty As They Wanna Be album was declared legally obscene by a Florida judge, the first album to earn the dubious distinction. Record stores were warned that they could be arrested for selling the album and at least one record peddler was arrested for selling a copy to an undercover cop (because they clearly had nothing better to do).

This, of course, made the band super-famous.

The rap group performed their first live show after the ruling the following June in Broward County, Florida, and made no concession to the obscenity laws. As such, three of the members were arrested. DJ Mr Mixx was spared because he didn't actually rap any of the offensive words; he merely spun records. At a similarly obscenity-protective event in Georgia, the group subverted the laws by having their fans sing the naughty bits for them. No one was arrested.

In an act of solidarity, rock group Too Much Joy went to Florida and covered a handful of 2 Live Crew songs. They got nine hours in jail and a heap of publicity for their efforts and were later acquitted of all charges.