Answer: Roy Orbison

The hip-hop group 2 Live Crew, best known for their controversial work in the 1980s and 1990s, managed to end up in a legal battle that took them all the way to the United States Supreme Court to square off against Roy Orbison.

In fairness, the 1994 case did not (sadly) see (the by then deceased) Roy Orbison and the hip-hop group actually appear in the courtroom together with a dramatic A Few Good Men legal showdown. The case was called “2 Live Crew vs. Roy Orbison” in the press, but strictly speaking, the landmark case had a much drier name: Campbell v. Acuff-Rose Music. The case was named after Luther R. Campbell (a.k.a. “Luke Skyywalker”, 2 Live Crew’s lead vocalist and owner of Luke Records”) and Acuff-Rose Music, Inc., the rights holder for Roy Orbison’s iconic rock ballad “Oh, Pretty Woman”.

The dispute started when Campbell approached Acuff-Rose Music to ask for permission to sample the song for a parody work 2 Live Crew was producing called “Pretty Woman”. Acuff-Rose Music declined to allow the sampling, but the group proceeded with the project anyway, releasing the song in 1989. The ensuing legal battle ended up at the Supreme Court and resulted in a landmark ruling in favor of parody works. The Court ruled that despite Acuff-Rose Music’s claim that 2 Live Crew’s version of the song devalued their original work, it was in fact a completely transformative work and that no reasonable person would ever, under any circumstances, confuse the two songs or the two artists. The world was, in a manner of speaking, filled with 2 Live Crew fans and Roy Orbison fans, and never the twain should meet.