“Pretty Woman,” by 2 Live Crew, and As Nasty As They Wanna Be, by 2 Live Crew - Known for its sexually charged lyrics, album covers, performances and, well, pretty much everything, 2 Live Crew became the most infamous band in America in 1989 when it released its magnum opus, As Nasty As They Wanna Be. Anti-obscenity activist Jack Thompson (an attorney who was later disbarred in 2008) instigated an investigation into the album in the hopes of getting it pulled from record stores. About a year after the album’s release, his efforts bore fruit after police obtained an order from Broward County (Florida) Circuit Judge Mel Grossman declaring the album to be obscene. To appease some of its critics, the band had released a “clean” version of the album that removed the explicit lyrics. The band added a newly recorded song, a parody of Roy Orbison’s classic “Oh, Pretty Woman.” This new song drew the ire of Orbison’s estate, which sued for copyright infringement.

Read our related cover story: “Lawyers, songs and money: Music that changed the law”