13 Times Ellen DeGeneres Made Her Guests Uncomfortable

For nearly two decades, Ellen DeGeneres was regarded as one of the nation's most beloved talk show hosts. Her uncanny humor, endless quirks, and ability to make even the shiest celebrities warm up to her made "The Ellen DeGeneres Show" a hit for many years. Not to mention the fact that it was one of the first daytime talk shows to have an openly gay host when it first aired in 2003. The show was packed with pranks, dancing, games, and heartfelt moments that allowed viewers to see some of their favorite celebrities in a different light.

The talk show may have been a success for many years, but it was also riddled with controversy. Several former "Ellen" employees alleged the show promoted a toxic work environment. According to a BuzzFeed News report, former staffers claimed they were terminated for taking time off for personal emergencies, were subjected to racist remarks, and endured a work environment characterized by fear and intimidation. DeGeneres apologized and multiple top producers were fired off, but the talk show ultimately came to an end in 2022.

However, it wasn't just previous staffers that stood up to the talk show host. Dozens of cringe-worthy videos of DeGeneres's interviews have racked up throughout the nearly 20 years that the show was on television. While the comedian does her best to get the dirt on celebrities' personal lives — sometimes the punchline comes at a cost. Here are 13 times DeGeneres made her guests uncomfortable.

It's common knowledge that if you're interviewing a guest, you need to do your homework. Especially if you're interviewing Katy Perry, whose chart-topping pop singing career makes her that much more Googleable. Ellen DeGeneres learned her lesson the hard way when she welcomed the "Dark Horse" singer onto "The Ellen DeGeneres Show" in 2017. During the interview, the talk show host made a major faux pas by forgetting with whom the "California Gurls" singer had previously tied the knot. 

During a dating game called "Will You Perry Me?" where the singer was asked to choose between potential suitors, Perry asked, "Do I have to get married? Again?" DeGeneres then told the artist, "You were not married," forgetting about Perry's former marriage to Russell Brand that ended in 2011. When the "E.T." singer reminded her, the television personality quipped back: "Oh yeah, I forgot about Russell." 

Perry then motioned for the producers to edit out the footage by mimicking scissors with her hands. "Remember you gave me some wedding gifts on this show?" she reminded DeGeneres. "That'll be cut out," the host joked. Perry was clearly taken aback by the ordeal, but DeGeneres quickly shifted gears to avoid any further mishaps. Yikes, we hope Brand wasn't tuning into this awkward sit-down. 

We all have our phobias. From spiders and ghosts to the imaginary monster under the bed, the sky's the limit when it comes to what makes our skin crawl. That being said, porcelain dolls don't exactly top the list when it comes to common fears. They do for Channing Tatum, however, as the actor revealed the delicate dolls are his biggest fear on "The Ellen DeGeneres Show" in 2014. 

"What are you afraid of?" Ellen DeGeneres asked the "Dear John" actor during the sit-down. While singing is a major fear for the actor, he added that he was "terrified of porcelain dolls." Tatum admitted that a possessed porcelain doll from a spooky television show might have brought about the fear, adding, "They're really super freaky." In true DeGeneres fashion, the host had a stash of porcelain dolls on hand to scare the actor. 

"Tell me you do not have a doll here," Tatum said before the talk show host brought out a doll. Uncomfortable is an understatement for how the actor felt about the confrontation, as the "Magic Mike" star curled up in his chair. "That is not right, look at it!" he exclaimed. "Why did someone make that?" When Tatum refuses to hold a doll, DeGeneres then brings one eye to eye with the star as he struggles to move away. "You're literally going to ruin my entire life," the actor said.

A First Lady pretty much has the world at her beck and call, so much so that Ellen DeGeneres thought she might retrain Michelle Obama on basic adult responsibilities. During the end of former President Barack Obama's second term in office, DeGeneres thought she might take Michelle on a trip to CVS pharmacy to help prepare her for life outside of the White House. In a 2016 clip from "The Ellen DeGeneres Show," a motorcade dropped the pair off at a local CVS to do their shopping, which turned into a cringey experience for Michelle. 

"You push the basket because no one is going to push it for you," DeGeneres told the "Becoming" author during the segment. The talk show host proceeded to open up merchandise before buying it, leaving Michelle anxious. "Ellen, don't open these up in the store!" she remarked to DeGeneres. "Why not?" she quipped back. Shouting on a megaphone throughout the store, and even putting on Halloween masks, the television personality was anything but subtle with the First Lady. 

DeGeneres went as far as scratching a store employee with a wooden back scratcher, while Michelle chastised: "This is not how you behave in a CVS. Stop scratching him!" Michelle even had to stop DeGeneres from jokingly signing a baby's forehead during the off-the-rails shopping excursion. We're not sure the former First Lady can ever enter a CVS again without DeGeneres popping into her head.

When you think of Martha Stewart, sexting isn't the first thing that comes to mind. It isn't the second or third either, but the chef might have a few hidden talents most don't know about. Ellen DeGeneres got personal with Stewart when she appeared as a guest on "The Ellen DeGeneres Show" in 2016, and they played a game of "Never Have I Ever" alongside Snoop Dogg and Anna Kendrick. 

The game started out with "Never have I ever sexted," with guests holding up a paddle with two opposite sides indicating if they have or haven't done the statement. Snoop, Kendrick, and Stewart all answered that they had indeed sexted before, but DeGeneres singled out Stewart. "Wow, Martha, you've sexted? Do you know what that is?" The "Martha Cooks" host replied: "I have used technology for a lot longer than you have, Ellen." 

The talk show host attempted to pry more answers out of the celebrity chef about who she sexted and when. "It doesn't say 'none of your business' on here," Stewart quipped back referring to her paddle. We knew Stewart knew how to spice up a kitchen, but apparently, her texting can bring the heat as well.

Justin Bieber is used to having his life exposed to the world, but when he signed up for a life of fame and fortune, we're not sure he was expecting to be photographed by paparazzi in the nude while on vacation. While traveling in Bora Bora and stepping out for some sun on the balcony of his private bungalow, Bieber got a bit more than he bargained for. Photos later surfaced of the singer baring it all with an unidentified woman in the background and the Internet went bonkers.

Ellen DeGeneres was on the case, and she got to the bottom of the photos when the "Believe" singer stopped by for an interview on "The Ellen DeGeneres Show" in 2015. When she asked Bieber how he wasn't aware of the photographers taking his photo, the pop star admitted he "wasn't really looking out for them." He revealed that the prying eyes had been staking him out in a boat, and his manager, Scooter Braun, called him a few days later to relay the news.

"It wasn't as bad as I thought it would be," Bieber said of finding the naked photo gone viral. When DeGeneres tried to get to the bottom of who the mystery woman was, Bieber admitted she was just a friend. "You just brought a friend to Bora Bora? And you're just naked with your friend?" DeGeneres joked. "Why are you putting me on the spot like this?" the singer said. "You're making me blush."

Cher wasn't exactly thrilled when she went on "The Ellen DeGeneres Show" to find the talk show host giving a horrendous impersonation of her. The singer was a guest on the talk show in 2018 when she joined DeGeneres at a hair salon to help style clients' hair. In the middle of blow-drying a customer's hair, DeGeneres asked, "Cher, have you slept with a girl?" While the artist answered "no," the talk show host's antics only escalated.

DeGeneres donned a black wig and began to perform Cher's song, "If I Could Turn Back Time," albeit with the wrong lyrics and completely off-tune. "Of all the bad [impersonations] I've heard on me, you know, this is probably the worst," the singer told DeGeneres. The host then questioned the lyrics of the song, saying, "If you could reach a star, you can't really give them to somebody. They would be hot." When one of the customers agreed with DeGeneres, Cher responded, "What do you mean 'yes,' you don't know her!" The television personality told Cher, "They know me better than they know you!" The singer replied laughingly: "Oh, you're such a b***h!"

Ellen DeGeneres isn't always tactful in her delivery. In fact, most of the reason her interviews were so popular for decades was for her lack of tact. When Celine Dion appeared on "The Ellen DeGeneres Show" in 2007, the singer got a taste of the talk show host's unapologetic questions when her son's haircut was brought up. When DeGeneres showcased a photo of Dion's young son sporting a shoulder-length haircut, she said, "It seems like you're busy with something because you're forgetting to cut your son's hair." 

The "My Heart Will Go On" singer seemed to get defensive over the host asking when she planned to cut it. "Do you have a problem with that?" she asked. Dion stood up for the decision to leave her son's hair long. "You know it's amazing right?" she said. "Some people shave the head of their children, and people say, 'Oh, isn't that terrible?' Well, I don't even cut my son's hair, and they say, 'Oh my God, when is she gonna cut her son's hair?'" 

The Grammy-winning artist went on to admit how impossible it is to please everyone being in the public eye. "My son makes the decision about this hair," she affirmed. "When he's ready, I'll cut it. And then when I cut it they'll say, 'You know what? It's a little too short.'" Given her sensitivity to the subject, DeGeneres quickly diverted the interview to talk about what Dion's music.

There's nothing more embarrassing for a talk show host than getting a guest's name wrong. Ellen DeGeneres is familiar with the faux pas, as the host did it herself when comedian Hasan Minhaj appeared on her show in 2019. Despite calling herself a big fan of the star, she botched the pronunciation of his name.

Minhaj used the flub as an opportunity to teach the rest of America the importance of correctly pronouncing people's names. "I actually want to do this on national television," the Indian-American said. "The real way you pronounce it ... it's HAsan MINhaj, and people always mispronounce it." He admitted it bothers him that people don't attempt to say his name correctly by just emphasizing the first syllables. "[They say,] 'I'm so sorry I can't pronounce it. Meet my son, Higsby Witherthrottle III," he joked. 

While DeGeneres eventually did get it right — after three attempts — the mix-up highlighted the difficulties people from different ethnic backgrounds face in Hollywood. On his Netflix show, "Patriot Act," Minhaj admitted he used the stage name "Sean" before making the decision to go back to his roots. "You'll have people who are like, 'This is my Chinese name, this is my American name.' But I'm like, 'Dude, f**k that.' Your name's your name," he remarked.

Guests of "The Ellen DeGeneres Show" better check twice to make sure they invite Ellen DeGeneres to their events. When Dakota Johnson appeared on the show in 2019, she got into an awkward exchange with the talk show host over a birthday party invite. DeGeneres insisted that the actor hadn't sent her an invite to Johnson's birthday party that year, which the actor denied.

After claiming that she wasn't invited to Johnson's 30th birthday celebration, the actor replied, "Actually, no, that's not the truth Ellen, you were invited." The "Fifty Shades of Grey" star admitted that she made sure to send an invite to the talk show host after DeGeneres gave her flack for not inviting her the year before. "But I didn't know you even wanted to be invited," Johnson added. "I didn't even know you liked me." The host quipped back, "Of course I like you, you knew I liked you." 

The actor reaffirmed the fact that DeGeneres failed to attend and even told her to ask her employees to confirm the invite was sent. Ultimately, DeGeneres admitted, "It was probably in Malibu, that's too far for me to go to." DeGeneres attempted to smooth things over by saying jokingly, "No, I think I do remember I was invited, thank you!" After this lesson in party manners, we're pretty sure DeGeneres will think twice before calling Johnson out again.

Hasn't everyone learned that it's not polite to call Taylor Swift out on her dating history? The Grammy-winning singer has endured a long history of the media scrutinizing her ex-boyfriends. But despite talking about her love life in several of her songs, Swift has made it clear that it's not fair game for her to name-drop her arm candy.

When Swift joined Ellen DeGeneres as a guest on "The Ellen DeGeneres Show" in 2013, the conversation quickly became about who the singer dated. The television personality insisted that the "Red" singer dated actor Zac Efron, who was previously a guest on the show alongside Swift. Even after the artist denied the claim, DeGeneres couldn't catch a hint. "We didn't date," Swift tried to convince her. The host responded, "Yes, you did! Why do you deny it?" 

When DeGeneres changed the subject to Swift's music, she still couldn't get off the topic. "Which song is about Zac on the new CD?" she asked. The host then played a slideshow featuring photos of Swift and other men and asked her to confirm whether she dated them. "This is ... the one shred of dignity that I have ... People go and make guesses about [who I've dated] and the only thing that I have is like that one card," Swift added. She exclaimed after she reluctantly played the game: "This makes me feel so bad about myself!" 

A woman should be able to announce her pregnancy when and where she wants. At least, that's what Mariah Carey thought after Ellen DeGeneres prematurely outed her pregnancy when she appeared on "The Ellen DeGeneres Show" in 2008. During the sit-down interview, DeGeneres mentioned that there were rumors swirling about Carey potentially being pregnant. "I don't discuss that," the "Always Be My Baby" singer replied. Carey didn't really have a choice in the matter, however, because the talk show host brought out champagne to toast to the singer. Carey eventually took a pretend sip of the bubbly while DeGeneres exclaimed, "You're pregnant!"

Looking back over a decade later, the singer has regrets about the way the segment went down. "I was extremely uncomfortable with that moment is all I can say," Carey admitted in a 2020 interview with Vulture. "And I really have had a hard time grappling with the aftermath." The artist revealed she had a miscarriage after the announcement, which was revealed only years later when she and her ex-husband Nick Cannon welcomed twins. 

"I wasn't ready to tell anyone because I had had a miscarriage," Carey told Vulture. "I don't want to throw anyone that's already being thrown under any proverbial bus, but I didn't enjoy that moment ... But what am I supposed to do?" She went on to add that there was "an empathy that can be applied to those moments" that clearly wasn't present. We're looking at you, DeGeneres.

Bachelor Nation contestant Corinne Olympios didn't exactly have a positive experience during her time on "The Ellen DeGeneres Show." The blonde beauty seemed all smiles during their sit-down in 2017, cracking jokes with the talk-show host and even accepting the fact that viewers may see her as "crazy." Despite their chummy interview, the reality star later admitted that the behind-the-scenes version of DeGeneres is not what fans see on television.

On a 2018 episode of "The Morning Toast" (per Life and Style), Olympios admitted she had high hopes for meeting DeGeneres but was let down. "I love Ellen so much, I thought I would be, like, talking to Dory and I was really excited and she made me so uncomfortable, unfortunately," she admitted. Olympios also mentioned that she had an unplanned run-in with the host backstage before the interview. "She was very cold when I saw her before the show, which I don't think I was supposed to, because everybody got very nervous when we bumped into each other and you could tell they were like, 'Oh, s***,'" she recounted.

Although Olympios said she still admires DeGeneres, she did call the host out for her misbehavior. Following the multiple accusations against DeGeneres by former employees in 2020, the Bachelor Nation star took to Instagram to share her thoughts. "I TOLD Y'ALL," the reality star commented on an Instagram post (per Life and Style) that detailed the host's alleged misconduct.

Harry Styles's dating life has been brought up time and time again in the media, and Ellen DeGeneres wasn't missing a shot at it either. When the English singer stopped by "The Ellen DeGeneres Show" in 2019 to sit down with DeGeneres, he seemed to get a bit uncomfortable when Kendall Jenner was brought up. While they never publicly came out as a couple, the two had the rumor mill buzzing since 2013 over a potential love connection between the two friends.

While Styles sat down with DeGeneres to promote his album, Fine Line, the talk show host didn't miss an opportunity to ask him about his relationship with Jenner. "And you and Kendall are really good friends now, right?" she asked the singer, which he confirmed. His body language seemed to hint at something more, however, as he nervously scratched his leg. DeGeneres then asked him whether or not his album was inspired by a break-up, alluding to a potentially ended romance with the model. Styles didn't give up the tea on who exactly he refers to in some of his sadder songs, adding that he wrote songs from difficult personal experiences he endured. 

While DeGeneres didn't crack the case on where Styles and Jenner stand, fans can decide for themselves what to make of the uncomfortable moment. Either way, Styles walked a fine line to dodge that line of questioning.