Next Question, Please: The Most Awkward Interviews Of All Time - Page 3
Share the post
Share this link via
Or copy link
Being a journalist is a tough gig. They have to investigate, discover facts and try to navigate huge egos. Sometimes, the interviews are fascinating. Other times, they’re fascinatingly awkward. Here are some interviews that were more awkward than your last E-Harmony date.
Kanye West and Jay Leno – Right after Kanye punched Taylor Swift in the boob and took her virginity on stage, he was apparently remorseful and took to Jay Leno’s formerly-funny show. What resulted was tons of silences and Kanye looking like he was about to go to time out.
Superhead and Jamie Foxx – Ms. Head hopped on the Jamie Foxx show and it started off peacefully at first. But in Foxx fashion he took it there, calling her every kind of hoe under the sun. She tried to call him gay and it all went downhill.
Love Bossip? Get more! Join the Bossip Newsletter
We care about your data. See our privacy policy.
Katie Couric and Lil Wayne – What in the blue fawk was Lil Wayne talking about? “Gangstas don’t ask questions” Who told him that? Oh yeah, then they went bowling.
Charlie Sheen and Anyone That Asks Him Questions – #Winning has become the slogan of the year, but anyone that tries to understand what he’s talking about is #Losing. We felt bad for the interviewer whenever Sheen opened his mouth.
Dennis Rodman and Jorge Sedano – What does anybody care what D Rod thinks these days? In a quest for relevance, Rodman called a Miami radio station to talk about the Heat. He did all of this while getting domed up by some random chick. Classy. We hope she took her penicillin shot.
R. Kelly and Toure – After “allegedly” peeing on a teenager, Kells took to BET for an in-depth interview. Toure asked a simple question about if the Pied Piper likes teenagers. Kelly then asked for a definition of teenager. *ahem* Quick question: does anybody believe the man doesn’t like little girls?
Ja Rule and Louis Farrakhan – This sit-down interview was just bizarre. Farrakhan was talking about peace for Ja and Fiddy, and Ja sounded like he just had his candy stolen. Poor baby. Hopefully he can link up with Louis’ connects in the clink and get some help.
Chris Brown and GMA – The actual interview wasn’t too bad, but Breezy got his blonde hair and panties in a wad afterwards. Apparently ol’ buddy feels like the victim of an a$$-whoopin’ he delivered, so he breaks stuff when he gets asked about it. Poor baby.
Kanye West and The Today Show – Kanye is reformed…right? Maybe rappers and R&B artists should stay away from morning shows, because West almost smacked Matt Lauer when the Today Show played the Swift incident video. Matt seems gangsta, though, and can handle his fair share of men if you know what we mean. Yeezy should watch out.
Michael Jackson and Martin Bashir – This was kind of like a long date, with Bashir examining MJ’s hands and ogling his moonwalking. Then apparently the whole thing was manipulated and it got ugly. Uglier, we mean.
- Sonja Norwood Defends Ray J From ‘Terrible Son’ Shade After His Arrest For Allegedly Pulling A Gun On Princess Love - Page 3
- Coordinated Couture Couple A$AP Rocky & Rihanna Sizzle & Slay 2025 Gotham Awards, RIHveal Fenty Family Holiday Plans - Page 3
- Turkey With A Side Of Shenanigans! Funniest, Wildest & Messiest Tweets, Viral Videos & More From Thanksgiving 2025 - Page 3
Stories From Our Partners
-
Whew Lawd! The Hottest Thirst Traps Of The Week, Vol. 122
-
Kandi Koated Konfirmation! A Look Inside Kandi Burruss & Todd Tucker's Prenup After Divorce Announcement
-
Turkey With A Side Of Shenanigans! Funniest, Wildest & Messiest Tweets, Viral Videos & More From Thanksgiving 2025
-
Guess Who’s Coming To Dinner: Celeb Couples Celebrating Their 1st Thanksgiving Together