The Coolio Moment On Jeopardy! That We'll Never Forget

The world was shocked by Coolio's sudden death on September 28, 2022. The iconic rapper was 59. His death was confirmed by his longtime manager Jarez, who spoke to TMZ about the loss. According to the outlet, Coolio was found unresponsive in his home. There was no sign of foul play or any drug or drug paraphernalia found near the rapper; cause of death will be determined officially through an autopsy and toxicology test.

"We are saddened by the loss of our dear friend and client, Coolio, who passed away Wednesday afternoon," Jarez said in a statement to the outlet. "He touched the world with the gift of his talent and will be missed profoundly. Please have Coolio's loved ones in your thoughts and prayers." Coolio, whose real name is Artis Leon Ivey Jr.,will be remembered for his many contributions to the music industry. Perhaps most notably for his 1995 Grammy-winning hit "Gangsta's Paradise."

The song became such a cultural phenomenon that it even found its way into a "Jeopardy!" question. The results were, well, almost as memorable as the song.

"A song by Coolie from 'Dangerous Minds' goes back in time to become a 1667 John Milton classic" asked the late "Jeopardy!" host Alex Trebe on a 2018 episode. While it's probably pretty cool to write something culturally significant enough for someone to craft a "Jeopardy!" question out of, that's not why this question stands out. The question and answer are memorable because, according to TMZ, the contestant famously fumbled the answer.

When Trebek asked the question, Alex was in the lead. He quickly pressed his buzzer and responded, "What is Gangster's Paradise Lost?" to put him well over the $10,000 mark. However, the song is called "Gangsta's Paradise," not "Gangster's Paradise." Trebek later tells the contestant that he mispronounced "gangsta" by adding an "er" at the end. To which then added, "So we take $3200 away from you and you are now in second place."

Coolio spoke to TMZ producers after the incident and said he would have let the pronunciation go, however, agreed the contestant was incorrect. He then shared some wise advice to a specific demographic, adding, "Let me explain something to you — and this is for white people: The -er will always get you in trouble. Never use the -er if you don't have to use the -e." What a legend.