A hush falls in the studio audience, and jaws drop in stunned silence. As friends and family watch at home, no one can believe what they just saw! Over the years, some unforgettable moments have been captured on-screen, and the cringe or tension could be felt through the satellite waves. Thinking about some of these moments can make your stomach flop, but at least we weren’t the ones in the hot seat!
A good late-night talk show will feature the hottest celebrities and have the audience on edge waiting for the tea to be spilled. It’s all about pushing the envelope and seeing just how far a host can push their celebrity guest before they get a reaction. Take a look at the most awkward and unforgettable late-night talk show moments ever!
When Jimmy Kimmel started hosting his late-night show, he was relatively unknown. He had co-hosted ‘Win Ben Stein’s Money’ for five years and was a surprising choice by cable network ABC. The host was a natural and instantly fell into the audience’s hearts, but would his celebrity guests feel the same?
In 2018, Kanye West was being interviewed by Kimmel and the conversation moved into politics. At the time West was vocal about his support for previous American President Donald Trump. As Kimmel asked West some triggering questions, the host was left shocked when West refused to answer. It was complete silence until an impromptu commercial break! The audience was probably cringing in their seat, but would this next celebrity’s advice calm everyone down?
Cardi B was a guest on Kimmel in 2018 and she wasn’t alone on the couch. At the time of her interview, well-known comic John Mulaney was also a guest. Cardi B is known for outrageous expressions to match her fiery vocal talent but no one was prepared for her pearls of wisdom.
Mulaney and Cardi began to discuss how they managed nerves while performing. Cardi B does a unique trick with precise volume control. As she coached Mulaney and Kimmel, even the audience was in on it, okurrrrrrr! Let’s go back in time and see how older hosts would connect with their guests.
Johnny Carson was one of the longest late-night talk show hosts in history. Over his thirty years, he had a variety of guests and found several ways to interact and connect over their interviews. However, this one episode had Carson working up a sweat!
When the infamous Zsa Zsa Gabor came on the show in 1966, audience members were excited to learn more about her life. Everyone got more than they bargained for when the host and guest played Twister for the entire segment. The episode skyrocketed the sales of the game and was a great episode! We think this next host bit more off than he could chew with a famous starlet.
In 1998 at the height of her ‘Friends’ fame, Jennifer Aniston was interviewed by David Letterman. A seasoned host, Letterman, was known for wild behavior when beautiful guests appeared on his show.
Without any warning or permission, Letterman shocked audiences and scared celebrities while he proceeded to put Aniston’s hair into his mouth. The moment is so cringe-worthy and would not have made it on today’s television!
Everyone was excited for the beautiful Raquel Welch to be a guest on ‘The Dick Cavett Show’. The starlet was known for her looks, and the host was noticeably impacted by being in her presence. Cavett was seen loosening his tie and trying to pull himself together, and audiences wondered if he would be able to complete the interview before fainting.
It was questioned if he could hold his own in an interview and folks cringed wondering how he would handle future female guests. Cavett got a chance to redeem his interview skills and also had the unknown privilege to speak to this famous performer the last time before the world lost her too young.
Janice Joplin appeared on ‘The Dick Cavett Show’ in 1970. No one knew at the time, but the host would be the last person to interview Joplin before her untimely death two months after the interview.
Fans have flocked back to hear her voice, see her magnetic smile again and watch the camaraderie between the host and his selected guest. Not all hosts and guests get along so well, and this next host was the exact opposite of the woman she had to interview in front of international audiences.
On May 20th, 1975, the Mistress of the Dark, Elvira, was a guest on the Tonight Show, and Joan Rivers was doing a guest spot hosting. Two women could not be more complete opposites, and RIvers was the first to mention their contrasting appearances.
At the time of the interview, Elvira was popular through her work on a local radio show. It would still be seven years for her film debut! This next celebrity was one of the most successful entertainers of her time. Would this host mess up his opportunity to conduct a good interview, or would it be a fan favorite?
When Houston was on the Jay Leno Show, it attracted a large audience! The singer was famous and, at the time, had sold the most albums of any female singer. Even the host was a little star-struck, to say the least.
The interview went smooth, and then it was time for Houston to perform. She chose to do her single ‘All The Man That I Need,’ and Leno was finally able to make one joke his audience quietly laughed at in the shadows. She had an incredible gift that no one could match, but this next talk show host tried something new and felt the pain from her decision!
Tyra Banks was a famous runway model and had a successful television series called ‘America’s Next Top Model.’ Would she be a popular talk show host as well to make her a triple threat? This four-legged guest was going to put a damper on her plans!
It wasn’t the human guest that got Tyra out of her chair but his prickly porcupine friend! The host hadn’t realized she was falling head over heels, and there was nothing the audience could do as she flipped over her chair during recording. Thankfully no one was injured, but will this next talk-show moment make everyone as uncomfortable?
On this day, Jay Leno had a full couch of amazing celebrity guests! The audience was going red from shock and embarrassment the longer this interview continued! Even the talented host, Jay Leno, couldn’t interrupt or make an excuse to make things better!
Actress Sofía Vergara talked about her love of pizza to fellow guest Gordon Ramsey, a popular British chef. Ramsey began to make cheeky comments about the way Vergara was eating, including how she “just picks it up and sticks it in.” Leno tried to change the subject, but this memory is burned into audiences’ minds everywhere! This next situation was a celebrity making their host sweat and the audience wondering just how far it would go!
The entertainer Madonna chose to do her first-ever talk show interview with Johnny Carson. In typical Madonna fashion, she had never needed to do one before and was excited but a little nervous to be chatting with Carson.
She decided to channel her nerves into aggressively flirting with Carson and making it clear she didn’t want to leave without him. In 1987 Madonna was already leading multiple revolutions, but even audiences around the world gasped at her blunt approach. This next host was left speechless by one line he didn’t see coming!
Jimmy Kimmel was so excited to have actress Dakota Johnson on his show; he might have forgotten interview etiquette. As Johnson tried to answer Kimmel’s quick questions, she finally had enough and said to him, “aren’t you supposed to let people talk on this show?”
Kimmel was speechless when he realized this fatal interview error, and the interview didn’t recover. Audience members were thankful they weren’t in Kimmel’s hot seat or this next young celebrity’s place when his host got a bit handsy!
In 2012 Justin Bieber was 18 years old and had just started getting tattoos. This wasn’t the first time the young singer had sat with Letterman, but this interview was different from the rest. Letterman is significantly older than Bieber, and the age gap really showed.
Bieber was happy to show off his new tattoo, “Believe,” which was also the name of his latest album release. As Bieber showed the tattoo to Letterman, the host began trying to rub off the permanent ink, to Bieber and the audience’s shock. Bieber wasn’t the only guest to experience uncomfortable touches in front of a studio audience.
Jimmy Kimmel was beginning his interview with Ivanka Trump when comedian Andy Dick just couldn’t keep his hands to himself. The businesswoman expressed being uncomfortable since she couldn’t see what Andy was doing behind her, and the comedian felt obligated to make his actions more visual.
Shocking television audiences everywhere, Andy proceeded to run his hands down Ivanka’s legs. He asked if she applied glitter to them backstage. The comedian’s bad behavior ended up getting him taken off the stage by security. No one could believe that security wasn’t called for this cringe-worthy moment on television!
Russel Brand is a comedian and television personality. He is known for erratic behavior, and hosts are never sure what they’ll receive if he comes on. This was a prime example of the wild behavior Brand is capable of in one quick segment!
At first, he began by fixing the desk he was sitting at, then started chastising the hosts about their manners and yelling at employees off camera. The final act of rebellious behavior was commenting on the anchor’s low-cut dress and saying he couldn’t help how he was feeling with her tempting him! Another starlet’s outfit choice got a wholesome host in hot water!
Pop sensation and leader of the girl-group Pussycat Dolls, Nicole Scherzinger, realized she had lost her host’s attention. Conan is such a wholesome host that it’s rare for him to run into problems, but his eyes gave him completely away this time.
Scherzinger was wearing a vibrant dress, but Conan was clearly more interested in the package than the wrapping. After Scherzinger commented for Conan to focus, the host apologized and laughed, and the interview continued. This next star thought his host wanted to trade insults, but apparently, he crossed an invisible line.
Sean Hayes had been a regular guest on the Ellen Degeneres talk show, but apparently, he couldn’t understand what the host wanted this time. Hayes and Degeneres are both role models for the LGBTQ community, but does Ellen see them as equals?
Ellen suggested they ask each other random questions during their segment, and Hayes casually admitted he thinks Ellen struggles to ask follow-up questions in interviews. The host was quick to insult Hayes and the cancellation of his tv show, ‘Will & Grace.’ The air was tense, even while Hayes tried to make light and laugh at the situation. This next host wasn’t sure what was about to come out of his guest’s mouth!
Barbeau was reaching fame through her broadway performances and tv sitcom, but Carson seemed out of topics to connect with her on. It was with relief that the host found out Barbeau had received an unusual Christmas gift.
Audience smiles quickly turned to grimaces while Carson began to pry about Barbeau’s personal life. She told him how her “multiple lovers” buy her strange gifts, but Carson couldn’t believe how busy her personal life was! Carson was surprised again by the skill of the next female guest.
Audience members thought this interview had started really well. Summers was thrilled to be on the show and told Carson this appearance made her feel truly like a star. It started to go off course when Summer said she watched Carson as a child.
No host likes to be reminded of their loss of youth, but at first, it didn’t seem to bother Carson. Later in the interview, Carson included Summer in a statement about women not being able to work on cars, and Summer put her foot down. Audience member’s jaws fell open as Summer was quick to make Carson eat his words and then wrap up the interview. This next guest was asked to spit it out on national television!
Joaquin Phoenix is very private and notoriously hates being interviewed. Unfortunately, being such a talented actor means he has to do a lot of press. Letterman interviewed the actor and was immediately put off by his body language and gum chewing.
The host couldn’t stop fixating on Phoenix’s “rude habit,” and finally, the actor had enough. On-screen for audiences everywhere, Phoenix took the gum out of his mouth and stuck it on Letterman’s desk! Another host tried to have an interview with Phoenix and faced similar results.
Jimmy Kimmel tried to interview Joaquin Phoenix, but after he began asking more personal questions, the star noticeably began to shut down and get more agitated. Choosing to ignore all the signs, Kimmel kept pushing questions until Phoenix loudly said, “this interview is so embarrassing.”
Audiences turned off the television, and ratings took a dive while Kimmel scrambled to end the interview on good standing. Another host seemed to get off to a rocky start and never regained her balance during the show.
Long-time friend and fellow comedian Sarah Silverman interviewed Bill Burr, but no one really knows what was going on. The conversation was defensive and awkward to watch, with the two going back and forth on if they liked each other or not.
Audiences could barely watch it was so cringy and uncomfortable but was it worse than a guest blatantly saying they didn’t like their host. One famous actress decided it was time this host knew he was living up to a despicable reputation.
He’s already made several appearances on our list but have you started to wonder if anyone is telling Letterman how out of line he is. After making several guests uncomfortable, Shirley McCain was ready to speak her mind and tell the host the truth.
During the interview, McCain tried to tell Letterman countless times to relax as his questions became more confrontational by the second. As Letterman continued to ignore her, she finally looked at him and said, “maybe you are an a***ole.” Audience members held their hands up to cover their shock and smiles. It had to happen sooner or later!
Conan O’Brien had the privilege to interview director Abel Ferrara, but he quickly wished he was anywhere else. The director arrived in an unclear state of sobriety and, at one point, escaped from the studio before his segment began.
After the crew tracked him down, he wasn’t in a massive conversational mood with Conan, and the poor host was floundering to make the interview worthwhile for him and the bored audience members. Do you remember one time when two hosts went up against each other for their own audience’s joy?
Since Carson retired and Leno got his coveted time slot instead of the predicted Letterman, late-night hosts have been on opposite sides of the field. Leno and Letterman grew up in the comedy world of L.A. together, but Letterman was a repeat guest on Carson’s couch. It was rumored he would always take over the show and audiences gasped as it went to Leno.
No host was quite as direct when insulting Leno as Kimmel. He came with a vengeance to let everyone know he didn’t think Leno was worthy of his late-night spot. One of the most memorable times was when Leno attempted to interview Kimmel, but it turned into Kimmel just insulting the host for the entire segment. Unfortunately, Leno was not quick enough to fire back as many shots as he received. Letterman has made more people uncomfortable than both hosts combined, including this royal example!
No one was sure what Paris Hilton expected when Letterman asked to interview her when she got out of jail. In 2007 Hilton did 45 days in prison for violating her probation. She was anxious to change her image, but Letterman wasn’t prepared to let it go.
At one point in the interview, Hilton looked like she might cry and told Letterman that he was hurting the feelings. For a moment, the host feigned interest and asked her if she was feeling better now before continuing the same line of questioning. Letterman’s idol may have taught him this from the very beginning.
On Sept 2, 1974, Carson got a chance to interview a singer he was a huge fan of. Carson loved Day’s entertaining personality, but he loved her wardrobe choice even more. In 1974, women’s fashion was changing, and Day had decided not to wear a bra on the talk show.
The host did a great job staying focused, and it wasn’t as cringe-inducing as it could have been. Unfortunately, another starlet thought she had outsmarted her host and went bright red when he made sure everyone knew how wrong she was.
Everyone knows that Conan O’Brien is proud of his Harvard education, and not many would risk insulting the host’s intelligence. However, not everyone is Jennifer Garner. The starlet was feeling extremely confident and said O’Brien misused a word.
The ginger host’s cheeks matched his hair color, but it wasn’t long until he brought out a dictionary and made Garner eat her words. As the camera zoomed in on the dictionary proof, it also caught the flush happening on Garner’s cheeks and neck. This next starlet was blushing but not for appropriate reasons.
Dakota Johnson had already made one late-night host blush; could she do it again? Ellen is notorious for trying to make her guests uncomfortable, but this time the tables were turned! Ellen asked Dakota about her recent birthday party and then quickly said she was upset she wasn’t invited.
Dakota couldn’t believe what she was hearing! She told Ellen that she had been invited and actually R.S.V.P’d that she couldn’t make it. Dakota then went further to remind Ellen about how much guilt she had thrown at the actress for missing out on previous invitations that the actress was shocked at Ellen’s response. This nice actress didn’t realize she was being looked at as something to own until this next host made their intentions crystal clear.
Young actress Uma Thurman was excited to be interviewed by David Letterman, and the actress was quiet, if not speechless, by the time the interview was done. While Letterman tried at first to carry a conversation with the stunning actress, he eventually couldn’t focus and asked Thurman if he was too old for her to date.
The star had no idea if the host was joking and clearly became visibly embarrassed while he continued questioning her tastes in romantic partners. Finally, the interview ended with everyone around the world shocked as Letterman told Uma she was a “lovely piece of work.” Letterman wasn’t embarrassed, but our next host forgot how to speak English in an unfortunate interview.
Actors have to learn different accents for their roles all the time and are used to hosts asking about this skill. It seemed for a minute Jimmy Kimmel completely forgot actors do this and instead asked Australian actress Katherine Langford where she learned to speak English.
The actress was visibly confused and didn’t understand if she had missed the punchline. As Kimmel continued to follow this line of questioning, the studio audience remained in shocked silence. Our next actress almost slapped her host for an inappropriate adjustment.
When Kristen Stewart went on The Stephen Colbert show, she expected professional questions and attitude. The star was ready to laugh and talk about her upcoming works but instead had Colbert’s hands a little too close to her body for comfort.
Colbert was attempting to be helpful as one of Stewart’s necklaces was interfering with her microphone. Instead of asking the young woman to fix her chain, he reached over and did it himself. The chain, however, was on Kristen’s chest. The actress was in shock at the host’s bold move and ended up taking off her necklace. This next famous actress was used to people asking her private questions, but why did this host render her silent?
Angelina Jolie is stunning, and the world has recognized her gorgeous features several times. Letterman decided he needed the young actress to know how he felt and told her several times in the interview how nice she smelled and how pretty she looked. Letterman said he personally appreciated the efforts, which only made Jolie look more confused.
Finally, Letterman decided to figure out if Jolie was single and asked her if she was still married. The host didn’t do his research, and Jolie was going through a public painful split. Instead of being embarrassed, the host tried to see if Jolie needed his support, which she politely declined. This next interview was doomed from the very beginning.
How an interview starts can predict how the conversation will go. Unfortunately, Jay Leno decided to start this interview by telling Judith Light he liked to pause her shower scenes in movies. The audience gasped and the interview didn’t recover.
All these hosts have one thing in common, they completely misread boundaries and overstepped into personal information. It’s a small measure of human decency to stop asking questions that make others uncomfortable. We don’t think most of these tactics would work today, and we still can’t believe they existed five or ten years ago!