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Awkward rap: The Celeb Edition, featuring Carrie Underwood and Tyra Banks

Nine famous people, famous for things that aren’t rapping, try their hand at the game

On Monday night’s episode of Jeopardy!, host Alex Trebek fulfilled a lifelong dream we didn’t know we had by rapping Drake, Lil Wayne, Kanye West and Desiigner lyrics on the show. The college edition episode featured a category called “Let’s Rap Kids,” in which Trebek recited a few lyrics from famous rap songs as clues. These songs included Drake’s “Started From the Bottom,” Lil Wayne’s “6 Foot 7 Foot” and Kanye West’s “Famous.” But nothing was better than when he rapped the lyrics to Desiigner’s “Panda.” Can we just take a moment for Trebek’s flow … let me know if y’all find it. We’re joking, but, of course, shout-out to Trebek for being a good sport about it. I mean, really, he kicked the week off right. In honor of the joy Trebek brought us, we’ve compiled a list of a few other times nonrapping celebs tried their hand at the rap game. And, of course, it got a little awkward.

Millie Brown from Stranger Things raps Nicki Minaj’s verse from “Monster”

Stranger Things Millie Bobby Brown raps Nicki Minaj’s classic “Monster” verse with the utmost attitude. Stopping from time to time for bleeps, Brown sort of held her own on the beat. Of course nowhere near Nicki Minaj, but she took a solid crack at it and did pretty well. Go on, girl.

Carrie Underwood, Hunter Hayes, Luke Bryan, Aloe Blacc rap The Fresh Prince of Bel-Air theme song

This one gets very awkward. A bunch of country stars, including Carrie Underwood, try their hand at rapping The Fresh Prince of Bel-Air theme song. Now, this song should pretty much be ingrained in everyone’s mind. Most of the stars here were on the struggle bus, but we appreciate the effort. Of course, the lone brotha Aloe Blacc held it down. If they didn’t know the theme song then, they definitely do now.

Taylor Swift lip-syncs “Amazing” by Kendrick Lamar

Although Taylor Swift is lip-syncing, this video definitely makes the cut. We’ll give it to her that she certainly knows the lyrics, but, girl, I hope you finally found the beat. This video gets us every time. Thanks, Taylor.

Nicole Richie and Kris Jenner rap “Shoop” by Salt-N-Pepa


This one might just be our favorite, because Kris Jenner, like, what were you doing? If you ever need a good laugh, this one’s it. I wonder what Salt and Pep would think … ?

Tyra Banks busts a freestyle while Bow Wow ad-libs

Boy, do we miss The Tyra Banks Show, because it brought us gems like this one. Remember when Tyra Banks busted out her freestyle skills? It sort of reminds you of your middle school lunch table cypher. We see you, Tyra. We too were MCs once in our minds.

Amy Poehler, Tina Fey and Lindsay Lohan do the Kevin G mathlete song from Mean Girls

Amy Poehler and Tina Fey are comedy gold. Many of us know Kevin G’s mathlete song from 2004’s Mean Girls. And we have to say, if the fictional character weren’t destined for great academic things, a rap career would’ve been in Kevin G’s future. Poehler and Fey are backed up by Lindsay Lohan in the video. They are no Kevin G, but it was a good laugh.

Tamera Mowry raps Big Sean’s “IDFWU”

Tamera Mowry’s sweet spirit stands in stark contrast to Big Sean’s song “IDFWU.” She’s like that friend you have who is such a good person, you want to hate but you can’t because she’s such a good person. Her substituting the swear word for “fudge” made our day in the best way possible. Big Sean definitely thought it was funny, as well. Tamera, girl, we don’t even want you to swear. Please keep saying fudge.

Mila Kunis raps Eazy-E’s “Boyz-n-the-Hood”

Mila Kunis might just be an “OG” from around the way. Something tells me Eazy-E has been bumped throughout the Kutcher household more than once. Keep being great, girl.

Wolf Blitzer learns how to Dougie from Doug E. Fresh at BET’s 2010 Soul Train Awards

So, we know Wolf Blitzer isn’t rapping here, but this one had to make the list. Although his “dougie” is broke, Blitzer caught the beat a few times. Take a look.

Gertrude “Trudy” Joseph is a senior at UMass Amherst and intern with The Undefeated. She will probably be either the youngest “Gertrude” you will ever meet or the only “Gertrude” you will ever meet. From the birthplace of basketball (shout to the entire 413), Trudy believes the “Kobe System” is the single most important commercial of our time.