Alex Trebek Jeopardy! hip-hop
Alex Trebek Jeopardy! hip-hop
Photo Credit: Amanda Edwards/Getty Images

15 Hilarious 'Jeopardy!' Hip-Hop Fails

Jeopardy! contests aren't very knowledgable about hip-hop. Here are 15 of the funniest Jeopardy! hip-Hop fails over the years.

The current rendition of Jeopardy! premiered in September of 1984. Hip-hop was still a baby at the time. (Run-DMC would release their landmark self-titled debut a couple of months prior.)

Over the decades, the two would go on to become very successful — even as the two entities rarely crossed paths. That has changed recently. Jeopardy! is a show that prides itself on covering every subject. And as the genre has gotten bigger, more hip-hop questions have been featured on the show, from single questions to full categories.

In 2020, it is reasonable to expect people who know a little bit of everything to know a little something about hip-hop. That is not the case. Contestants are constantly getting Jeopardy! hip-hop-based questions wrong. Sometimes the questions are tough — sometimes they are easy. (Like in 2017, when Jeopardy! asked contestants who rapped "Panda, panda panda panda panda panda panda...")

With that being said, let's take a look back at 15 of the funniest cringe-worthy Jeopardy! hip-hop fails over the years.


Ken Jennings is known for being the greatest Jeopardy! player of all time. In 2004, he won 74 games in a row, ranking in over $ 2 million. He made his return in 2014 for Jeopardy! Battle of the Decades. While he displayed his hip-hop trivia skills (which were sharp). But, he struggled with one very simple Beastie Boys question.  

What "fat" rapper has beefed with 50 Cent?

You don’t have to be a purist to know about rap beef. When they came to this 50 Cent opponent there was silence. Nobody guessed Fat Joe. But, to be fair, 50 has feuded with so many people it’s hard to keep track. "Humble."

The contestants apparently weren’t listening to any radio in 2017. Because when Kendrick Lamar dropped DAMN. all these songs were played everywhere. 

Life of Pablo fail.

Kanye West is probably still somewhere working on Life Of Pablo.

Confusing Queen Latifah with Ellen?

Bet she would have gotten this right if this was a question about 2010 romantic comedy Just Wright.


This will probably be the first and last time Future's real name, Nayvadius, will be said on Jeopardy!

Steve doesn't know who Drake is.

Damn, Steve. Hip-hop was not your topic.

Window pane/pain. Get it?

The bar was low for these contestants. See what we just did there?

What's the difference between "on" and "in?" About $1,000, Arthur. Beat it.

The contestants did pretty well with the Beyoncé category. However, Arthur struggled with one simple #BeyHive question.

"What is Bey-Z?"

Seriously, what is Bey-Z?

Please play The Blueprint for these people.

Another appearance from Steve. What do you think he listens to?

Range look like Laffy Taffy.

The contestants had no chance. We imagine they didn't listen to a lot of Killa Seasonback in the day. 

That is not Kid Cudi.

Should we be more impressed that she knew who Kid Cudi was or mad that she thought that was a picture of him? 

Alex has bars.

This is one of the more memorable Jeopardy! categories because we get to see Alex Trebek rap. It's unfortunate that Alex, the contestant, doesn't have the bars Alex, the host, has.

No love for Solo.

At least Solange got a good laugh out of none of the contests knowing her album that literally came out last year.


Elga Roberson is an Oakland, Ca-based freelance writer. His unique takes on satire to social issues and all points in between can be read on his Medium. Feel free to follow him on Twitter