The Most Awkward Talk Show Interviews Ever

What are the most awkward talk show interviews ever? Daytime and late-night talk shows are some of television's most entertaining viewing options. From the hilarious interviews and skits performed on The Tonight Show Starring Jimmy Fallon to the political commentary on The Late Show with Stephen Colbert, talk shows have proven to be central to the television landscape.

Since most talk shows are filmed in front of a live studio audience (pre-pandemic, obviously), some of the in-person viewers have witnessed tense moments between the hosts and their celebrity guests. Maybe there was drama between the talent and the host backstage, or perhaps they have a history of not liking each other. Sometimes the interviewer hasn't adequately prepared for the interview, while other times hosts have been flat out mean.

Have you ever wondered what really happened between Ellen DeGeneres and Dakota Johnson, who's undergone a stunning transformation? What about the time Jimmy Kimmel had to cut to commercial because Kanye West wouldn't answer a question? To that end, we scoured the internet in order to track down the most tense and awkward talk show interviews ever. So without further ado, here they are.

Sometimes it's okay to forget the name of your friend's ex-boyfriend. But it's a whole other thing when someone forgets a public divorce, and this exchange between Katy Perry and Ellen DeGeneres is no exception. While on The Ellen DeGeneres Show in 2017, DeGeneres asked Perry to play "Will You Perry Me?" — a spin off of the game "Who Would You Rather?" In response, Perry asked, "Do I have to get married again?" to which the host responded, "You were not married." 

While in front of the audience, DeGeneres had forgotten that Katy Perry, who has a pretty strange love life, had been married to Russell Brand. The couple got married in 2010 and were only together for 14 months, but the moment was painfully awkward. To make matters worse, the Teenage Dream singer reminded DeGeneres that she had given the newlywed gifts on the show years back to celebrate the occasion. Yep... awkward. 

Perry then made a scissor motion with her hand, letting production know that part of the interview should be cut, but they clearly didn't listen. The whole interview is still on the internet!

Who would've thought that dentistry could so scandalous. While on The Tonight Show Starring Jimmy Fallon to promote her movie The Peanut Butter Falcon, Dakota Johnson reluctantly shared the story behind the disappearance of her tooth gap. The story of the orthodontic change had been in the headlines and Jimmy Fallon wasted no time bringing it up. "The fact that this is a newsworthy event in our world right now is pretty Chaka Khan to me," Johnson said. 

Johnson went on to explain that a permanent retainer she'd had since age 13 had been taken out, as it was causing the actress neck pain. As a result, her tooth gap had closed naturally. The whole awkward exchange escalated when Fallon tapped on Johnson's teeth with his finger to see if they were fake, while the audience let out some tense giggles. 

Before the interview moved on, Johnson had some choice words. "I'm sad about my gap tooth too, so I'd really appreciate some privacy at this time," she said, in what could have been a joking manner, but the whole talk show interview was too awkward to tell.

Dakota Johnson has had some pretty awkward interviews with some subsequent viral moments, but none come close to the painfully awkward exchange between her and Ellen DeGeneres, who's undergone a stunning transformation. While on The Ellen DeGeneres Show in November 2019, Johnson's October birthday party made its way into the conversation — and everything went downhill from there. "How was the party? I wasn't invited," DeGeneres blatantly asked.

The host clearly spoke too soon, because Johnson informed her — calmly, we might add — that she was in fact invited. "I did invite you and you didn't come," Johnson responded. She added that the host should ask her producer about it, and they confirmed (while the cameras were still rolling) that DeGeneres was out of town at the time of the party. "Oh yeah, I had that thing," DeGeneres said as a quick comeback. 

It turns out the host did in fact have "a thing" — she was attending a football game with George W. Bush, according to CNN. Perhaps that's why Dakota Johnson probably isn't a fan of Ellen DeGeneres.

We think it should be a rule to not bring up a lady's age during an interview, but Megyn Kelly didn't get the memo on an episode of Today. While interviewing Jane Fonda and Robert Redford during a segment on NBC, Kelly took the interview in a really awkward direction. Fonda and Redford were on the show to talk about their movie Our Souls At Night, but Kelly ended up expressing her thoughts on Fonda's appearance. "You're an example to everyone in how to age beautifully and with strength and unapologetically," Kelly stated. "You admit you've had work done, which I think is to your credit, but you look amazing," Kelly continued. That's when things got really awkward on the talk show.

The line of questioning was clearly not something that Fonda was prepared for, because the look on her face really said it all. "We really want to talk about that now?" Fonda asked, clearly uncomfortable. The actress quickly pivoted the conversation back to the film, saying, "Let me tell you why I love this movie we did, Our Souls at Night, rather than plastic surgery."

Russell Brand's appearance on MSNBC's Morning Joe might go down in history as one of the most awkward on-air interviews to ever take place, thanks to the hosts' lack of preparation and the interviewee's expectations. While promoting his 2013 tour The Messiah Complex, the comedian sat down with host Mika Brzezinski. Clearly unprepared for Brand's specific conversational style and intellect, Brzezinski quickly handed the reins to BBC's Katty Kay, but things went downhill from there. 

As the hosts started speaking over Brand, referring to him by the first name "Willy" instead of Russell — clearly poking fun at his expense — the comedian grew visibly frustrated and eventually called out the hosts for their "casual objectification" of him. 

In an opinion column later published in The Guardian, Brand wrote about his awkward experience on the talk show. "When I landed in my chair, on camera, and was introduced to the show's hosts...it became clear that, in spite of the show's stated left-leaning inclination, the frequency they were actually broadcasting was the shrill, white noise of dumb current affairs," Brand wrote. Yikes.

We're not entirely sure if talk show hosts have natural conflicts with one another, but that definitely seemed to be the case when Wendy Williams appeared on The Ellen DeGeneres Show. The interview started off on awkward footing when Ellen DeGeneres — who's undergone a stunning transformation — complemented Williams for her long-running career and the renewal of her show. The body language and the awkward pauses shared between the two hosts was palpable, and things got even worse from there. 

During the interview, DeGeneres suggested the pair play "Heads Up," a celebrity-based guessing game. While trying to get DeGeneres to name "Justin Bieber" without letting his name slip herself, Williams said that DeGeneres actually resembled the male singer. "As much as I want to not like him, I love his new song, and he really is cute," Williams said. "Some people say that he looks like you." Clearly reacting to DeGeneres's shocked expression, Williams looked to the camera and said, "I've heard that. You've never heard that? They say it in a good way." This interview was just cringeworthy from start to finish.

We all know that talk show hosts have had to adjust their shows during the pandemic, opting for Zoom calls instead of live appearances. Of course, some technical difficulties are expected, but this Lady Gaga interview on The Tonight Show Starring Jimmy Fallon was downright awkward. After announcing a global benefit to support healthcare workers that would feature the "Pokerface" singer, host Jimmy Fallon called Gaga while on the air to discuss. "I can't, Jimmy. I can't talk right now. I'm really sorry, it's just like a really weird time," Gaga said during the impromptu interview. "I can't see you. Am I on TV?" she then asked, clearly unaware of what was going on. 

Gaga quickly pivoted and told Fallon that she'd talk at a later date, and once again re-appeared on his show the following Monday. "I'm so sorry," she confessed. "We weren't quite ready yet, and I really appreciate you being so nice about it." Overall, the cringe-worthy exchange serves as a friendly reminder to always confirm your Zoom dates before you hop on the call.

We'll admit that it's tough to take compliment after compliment from someone you don't know well, and this interview on The Wendy Williams Show is full of that. While interviewing musician Billy Ray Cyrus, Williams dished out praises like there was no tomorrow — clearly at the discomfort of her guest. "I like your hair. It's really long. Still the mullet," she observed. "I see where your daughter gets her eyes," she continued. "Your eyes are hypnotizing. You're a very good looking man. And so is your wife." Yep... you read that correctly. 

Cyrus seemed to brush off the odd comment about his wife, but things got even more awkward when Williams forgot his daughter's name. "Your daughter. Her name starts with a 'T,'" Williams said. "I'm forgetting her name... the one who was on MTV." The Cyrus daughter she was referring to was actually Noah Cyrus, who, by the way, says growing up in Miley's shadow was "unbearable." He had to correct the host while sitting next to her! We're just going to file this one away under most awkward talk show interview ever.

It's common knowledge that Kanye West is bold in his political commentary. But things got awkward when the rapper and reality television star appeared on Jimmy Kimmel Live! in 2018. Host Jimmy Kimmel blatantly questioned West about Donald Trump, specifically seeking his thoughts on Trump's stance on race issues. "You so famously and so powerfully said 'George Bush doesn't care about Black people,'" Kimmel revealed. "It makes me wonder what makes you think that Donald Trump does, or any people at all." 

The question seemed to resonate with West, but instead of answering, the singer tilted his head to one side and said nothing. Due to the silence on West's part, Kimmel then announced that they should go to a commercial break. 

After the awkward appearance, West quickly took to Twitter to defend himself, saying that he and Kimmel had a good chat. "I'm reading that I was stumped by a question," he wrote. "Let me clarify the click bait. I wasn't stumped. I wasn't given a chance to answer the question."

Talk shows often have dramatic and awkward encounters, and this little spat between Kelly Ripa — who's undergone a stunning transformation — and Michael Strahan qualifies as both. In the wake of the news that Strahan would be leaving Live With Kelly and Michael for Good Morning America, Ripa used one of their last co-hosted shows to bring up Strahan's divorces... in front of a live studio audience. After reading an article in the New York Post about divorce, Ripa turned to Strahan for insight. "I don't have a take on it, but I want yours," Ripa said to her co-host. "You've gotten divorced." 

Strahan's eyes quickly widened in shock at the line of questioning. The two went back and forth until Strahan went on the defense. "I look at it like this. If you are in a relationship with someone, hopefully there was love there at some point or you wouldn't have been in a relationship with them in the first place," he explained. "Things change." Talk about awkward!

Strahan departed the show only a few weeks later. We wonder why.

We can file this one under an honest mistake, but that doesn't make it any less awkward. When interviewing actor Martin Short on Today in the lead up to his voice appearance in Madagascar 3: Europe's Most Wanted, Kathie Lee Gifford asked Short about his personal life, specifically about his wife, Nancy Dolman. "You and Nancy have got one of the greatest marriages of anybody in show business," Gifford said during the interview. "How many years for you guys?" Gifford clearly had not been briefed on the topic, as Dolman had sadly passed away from ovarian cancer two years prior, as noted by The Hollywood Reporter. 

But in his good natured spirit, Short went along with the interview and responded that they had been married for 36 years. The interview naturally progressed and eventually went to commercial, where Short informed Gifford of the on-air mistake she'd made. That's a big yikes if we've ever witnessed one.

The Ellen DeGeneres Show was investigated due to allegations of workplace hostility, but tension was already in the air way back in 2007. That's when famed singer Celine Dion pushed back on Ellen DeGeneres' line of questioning regarding her son's hair. 

Celine Dion was on the show to promote her newest album, but DeGeneres used the interview as a way to bring up the singer's family. "It seems like you're busy with something, because you're forgetting to cut your son's hair," DeGeneres said to Dion in what was supposed to be a jovial manner. She then displayed a family photo in which Dion's young son, René-Charles Angelil, was pictured. "Look at him," DeGeneres continued. "He is beautiful, but look at his hair. When are you going to cut that hair?" 

DeGeneres should've stopped when she was ahead. "Do you have a problem with that?" Dion quickly clapped back. "No, I don't have a problem," DeGeneres said. "That is some long hair." Tension built very quickly, and Dion eventually said that whatever she does, she won't please everyone. Wow.

Some awkward talk show interviews have truly stood the test of time, and this one is right up there with the rest. When on The Tonight Show Starring Jimmy Fallon to promote his album, country singer Blake Shelton was clearly irritated by Fallon's jokes, lack of questions, and overall interview tone. 

What started as a light-hearted joke poking fun at Shelton's album cover — which featured a photo of Shelton and the text "Texoma Shore" — quickly shifted direction after Fallon took things a little too far. Shelton eventually accused Fallon of "making fun" of his album cover, and arguably disengaged from the interview by looking down at the floor. 

The country singer followed the awkward interaction by saying, "Can you try to help me sell records for once?" and even asked the host if he had plans to actually conduct an interview. Even a well-intentioned line of jokes can sometimes go a little too far.

We saved the most awkward talk show interview for last, and this one even hurts our hearts a little. While on Jimmy Kimmel Live! actor Joaquin Phoenix became visibly upset due to the tense nature of Kimmel's questioning. 

Kimmel started the interview by asking Phoenix slightly invasive questions about his weight loss, and the nature of the questions clearly threw Phoenix for a loop. But the situation escalated when Kimmel showed footage from the set of Joker, which starred Phoenix in the title role. In the short clip, Phoenix can be seen scolding someone named Larry (who turned out to be the film's cinematographer) for making him break his concentration. 

Cut back to the interview and Phoenix was clearly upset that the clip had been shown. "It's just so embarrassing," the actor said. "That was supposed to be private. I'm sorry about that. Sorry you guys had to see that." Phoenix continued by saying that his publicist would issue a formal statement the following day about the awkward exchange. "Can we move on?" he added.