25+ Of The Most Awkward Celebrity Interviews Of All Time 

Network: OWN
Celeb Net Worth: $600 million*

Of course, we have to start this list with the OG of awkward celebrity interviews: Tom Cruise jumping on WBD Oprah Winfrey’s couch. This took place in 2005, and it showcased Cruise’s unique personality.

Tom Cruise Jumps On A Couch @diply/Pinterest

Cruise and Winfrey were friends, but the two didn’t really see each other after Cruise jumped onto Winfrey’s couch while expressing his excitement about his relationship with Katie Holmes. Considering how that love story ended, we’re sure Cruise regrets his bizarre, manic couch-jumping moment. 

Network: CBS 
Celeb Net Worth: -$2 million*

For eighty minutes in 2019, Gayle King with CBS sat down with R. Kelly for an interview, during which the star was to discuss allegations made against him (allegations that later became convictions, and now, Kelly is in a jail cell).

R. Kelly’s Gayle King Interview @chicagotribune/Pinterest

The result was an unhinged, soundbite-filled (“I’m fighting for my f**king life!”) interview that made the “Ignition” singer look even more guilty, if that were possible. Clips of the PARA sit-down went viral, and let’s just say this interview didn’t help Kelly’s case. It did, however, help cement Gayle King as an excellent, level-headed interviewer.

Network: ABC 
Celeb Net Worth: $70 million*

One of the most startling interviews on this list is Britney Spears’ 2003 sit-down with Diane Sawyer for Primetime Thursday on ABC. The interview was awkward at best and misogynistic at worst. Sawyer asked very combative questions throughout, and it almost seemed like she was bullying Britney.

@BritneyStrciker/YouTube

She commented on how little clothes the pop star wore and questioned if she “liked” how her voice sounded. Sawyer even defended threats against Spears, seeming to insinuate that she felt the starlet set a bad example for women and girls. 

Network: CBS 
Celeb Net Worth: $2 million*

David Letterman has long gotten heat for his track record with female celebrities, and one such celeb is Lindsay Lohan. In 2013, Lohan sat down with Letterman to promote Scary Movie 5. But, David Letterman had other plans for the interview.

Letterman Lohan Interview @theoklahomanvideoarchive3763/YouTube

He spent the whole time talking about whether Lindsay was going to return to rehab for her addiction issues. He also asked her whether she was a thief, as well as if she was managing her money responsibly. Lohan reportedly cried at the pressure, claiming this was never talked about in the pre-interview.  

Network: KTLA 
Celeb Net Worth: $250 million*

Samuel Jackson and Laurence Fishburne: two incredible actors who are not the same person. In 2014, a news anchor for KTLA was interviewing Jackson when he confused him with Laurence Fishburne.

Samuel Jackson Gets Confused With Laurence Fishburne ©u/Chef_Boyardee_thicc/Reddit

Jackson didn’t take kindly to this gaffe, stating that Black people “don’t all look alike.” He slammed the reporter’s lack of preparedness and professionalism, quipping, “There must be a…short line for your job outside there.” 

Network: CBS 
Celeb Net Worth: $300 million*

No, you didn’t read that title wrong—that’s what happened. David Letterman, who gets creepier as this article goes on, was interviewing Jennifer Aniston years ago when he said to her, “I just want to try one thing.”

David Letterman Chews On Jennifer Aniston’s Hair @metrouk/Pinterest

He moved closer to her, took a strand of her hair, and put it in his mouth to chew and suck on it. Shocked, Aniston jumped away and said, “What are you doing?” She had to use a napkin to dry off her hair, and she was no doubt rattled by the bizarre, Letterman-esque encounter.  

Network: NBC 
Celeb Net Worth: $3 million*

Marc Summers, a game show host, and Burt Reynolds, an actor, were both Tonight Show guests in 1994, and they didn’t get along. Summers made a crack about Reynolds’ divorce, and the actor became visually upset.

Burt Reynolds Gets Childish @buzzfeed/Pinterest

He retaliated by pouring his coffee mug of water onto Summers’ lap. Summers then grabbed Jay Leno’s mug to do the same, but Reynolds blocked it with cat-like reflexes, dumping the water onto Summers’ head. Leno, for his part, stayed far out of the way.    

Network: NBC 
Celeb Net Worth: $1.1 billion*

A lot has come out about Ellen DeGeneres in recent years, and not a lot of it positive. Accusations of guest mistreatment and a cold personality are chief among these allegations, along with creating a toxic work environment.

Taylor Swift Cries On Ellen’s Show @TheEllenShow/Youtube

One interview that The Ellen Show probably wants to forget is this one with Taylor Swift. The host displayed actors’ pictures on-screen, telling Swift to ring a bell when she saw an ex. This made Taylor so embarrassed, she was on the verge of tears begging Ellen to stop it.

Network: TBS 
Celeb Net Worth: $14 million*

Conan O’Brien has been pretty much unproblematic, and it’s hard to find a reason to have an issue with the guy. That said, Pussycat Doll member and singer Nicole Scherzinger had to put him in his place during one interview.

Conan O’Brien Looks Down @Google/Pinterest

Nicole caught Conan staring, well, not at her face, and she called him out, saying, “Focus, Conan.” O’Brien doubled down, saying, “You didn’t think I was gonna look down there?” about her low-cut dress. Yikes.

Network: TikTok
Celeb Net Worth: $40 million*

“What’s your favorite New York City staple food item…pizza or a hot dog?” This rather mild question was a softball that Rye Myers threw to actor Tony Danza, and, for some reason, Danza took that personally.

Tony Danza’s Not Keen On Rye Myers @buzzfeed/Pinterest

“You know what you gotta do, buddy? You gotta come up with better questions,” was Danza’s reply, for which he came under fire. Rye Myers would later make a TikTok about the interview, calling Danza incredibly “rude.”

Network: NBC 
Celeb Net Worth: $3 million*

In 1994, comedian Bobcat Goldthwait went on The Tonight Show with Jay Leno, and chaos ensued. After telling Leno he loved him “very much,” Bobcat lit Leno’s chair on fire with a lighter he pulled out of his pocket.

Bobcat Goldthwait Lights His Chair On Fire @Google/Pinterest

Leno reacted quickly, putting the fire out with the cup of water he had sitting on his desk. “Now you have to sit in this,” he told Bobcat, pointing out the ashy mess that could have been a bigger disaster, had he not acted fast.

Network: NBC 
Celeb Net Worth: $80 million*

In 2003, Jennifer Garner appeared on Conan O’Brien’s show and stopped the interview to, rather nastily, correct O’Brien’s grammar. Conan had used the word, “snuck,” to which Garner took offense.

Jennifer Garner Gets Told Off By Conan (Sort Of) @imgur/Pinterest

She made a quip about him having gone to Harvard, and O’Brien wasn’t having it. During a break, he had someone bring him a dictionary, where he read Garner the definition of “snuck” to prove her wrong.  

Network: Unconfirmed 
Celeb Net Worth: $1.4 billion*

“I’m not looking for a man, let’s start there.” That was Rihanna’s iconic response to an interviewer who asked her about what she was looking for “in the next man.” This question was pretty tone-deaf, as it had nothing to do with the reason Rihanna was at the event the interviewer was.

Rihanna Shuts Down A Sexist Interview Question @babisuni93/Twitter

The musician was promoting her Macy’s fragrance launch in 2014 when the awkward question happened. True to form, Rihanna shut it down, teaching the interviewer, a woman, a lesson about being tone-deaf.   

Network: Extra TV 
Celeb Net Worth: $165 million*

Jeremy Renner and Scarlett Johansson are two major parts of the Marvel MCU, and they sat down with an Extra reporter for an interview in 2012 to promote the Avengers’ latest movie. During the interview, the reporter asked ScarJo if she wore underwear underneath her Black Widow costume.

ScarJo Gets Asked About Her Underwear @extratv/Youtube

“Since when do people ask each other in interviews about their underwear?” Johansson shot back. She refused to answer the inappropriate question, saying instead, “I’ll leave it up to your imagination.” The “you perv” was silent.