Answers Can Cause a Dilemma

Every now and then, an answer’s pronunciation leads to a dilemma. Here’s an example from 2018. Nick Spicher buzzed in to answer this wordplay clue: “A SONG BY COOLIO FROM DANGEROUS MINDS GOES BACK IN TIME TO BECOME A 1667 JOHN MILTON CLASSIC.” The correct answer would’ve been “What is Gangsta’s Paradise Lost.”

Spicher said, “Gangster’s Paradise.” Since the words “gangster” and “gangsta” have two different definitions, he lost the round. That answer changed the overall meaning of the response.