Taylor Swift’s dating history is almost as newsworthy as her music career. Like most of us, however, she would rather not talk about her famous exes. Unfortunately, Ellen DeGeneres didn’t give her a choice.
During their interview, Ellen projected images of Taylor’s exes on a massive screen, basically implying that she had dated many men. Though a visibly-uncomfortable Taylor told the host, “I don’t know if I’m going to do this’” in regards to rehashing her past relationships, Ellen said, “yeah, you will.” Talk about awkward!
Madonna and David Letterman on a Mission to Make Us Uncomfortable
It takes two to tango, and in this case, it took two celebrities to make television viewers deeply uncomfortable. When Madonna stopped by the David Letterman show in 1994, things quickly got weird. First, David began pressuring her to kiss a random person in the audience, refusing to take no for an answer.
Then, Madonna made everyone cringe when she revealed she had given David a pair of her undergarments, telling him to show the audience. The interview was so uncomfortable and inappropriate we couldn’t turn it off fast enough!
Jesse Eisenberg’s Strange Attempt at Flirting Goes Viral
While promoting his magician-themed film “Now You See Me”, actor Jesse Eisenberg subjected us to an interview that we really wish we hadn’t seen. The actor, who was being interviewed by entertainment reporter Romina Puga, began flirting with the presenter in the most awkward way we’ve ever seen.
From snippy banter to Romina jokingly (we hope) referring to her guest as a “jerk” to her referencing them being in a relationship — the whole thing made us feel confused. He may have magic skills, but his flirting skills need some brushing up!
Mila Kunis Shuts Down Reporter in Two Languages!
It doesn’t hurt to have someone on your team who speaks the local language. Just ask Justin Timberlake! When he and “Friends With Benefits” co-star Mila Kunis were being interviewed by the Russian press, Mila (who speaks Russian fluently) immediately intervened after Justin was asked a rude question.
After the reporter asked why Justin was now appearing in movies (implying he should stick to music), a visibly irked Mila shot back asking the reporter, “what kind of question is that? Why are YOU here?” The video must be seen to be believed!
Ellen’s Outrageous Way to Get Mariah Carey to Confess
While it’s quite common for talk show hosts to tease answers out of their celebrity guests, it’s often done in a tasteful and humorous way. Sadly, that wasn’t the case when singer Mariah Carey visited the Ellen DeGeneres show in 2008.
The host demanded that Mariah address the rumors of her pregnancy, even pressuring her to drink an alcoholic beverage to prove that she wasn’t pregnant! Naturally, the mom-to-be was forced to admit her very private news, later calling the event “extremely uncomfortable”. Not cool, Ellen!
Madonna + Courtney Love = Epic Levels of Awkwardness
When two major music icons collide, there’s bound to be an uncomfortable level of tension. In 1995, while being interviewed at the MTV Video Music Awards, Madonna’s interview was interrupted by Courtney throwing a makeup compact at her. “Courtney Love is in dire need of attention right now,” Madonna remarked
After being invited to join the interview, a clearly inebriated Courtney and Madonna engaged in a conversation that ran the gamut from uncomfortable to plain catty. Madonna even implied that Courtney should leave show business. A must-see in award interview history!
Howard Stern’s Cruel Questions
As one of the world’s most famous shock jocks, Howard Stern is known for his no-holds-barred style of interviews. Though fans often like his uncensored schtick, it often crosses the line, such as when he interviewed the late Anna Nicole Smith.
The former “Playboy” centerfold and Guess model had been struggling with her body image, but the radio host kept asking her about her weight. At one point he asks her “get on the scale, and we’ll guess your weight.” Thankfully, the late reality star had enough sense to refuse this outrageous request.
Christina Hendricks Refuses to Have Her Body Discussed
Some celebrity interviews are famously awkward due to something that happened behind the scenes. In 2012, “Good Girls'' star Christina Hendricks was being interviewed when the topic of her famously curvy figure came up.
After being referred to as “full-figured” by Australian fashion editor Kate Waterhouse for Sydney’s Sun-Herald, the actress asked that Kate not use the term. After using the phrase a second time, the “Mad Men” star lost her cool and called her out on it, telling her off camera “I think calling me ‘full-figured’ is just rude”. We couldn't agree more!
Katharine Hepburn’s Legendary Quip About Pants
You would think that being a Hollywood icon with multiple awards would mean not having to discuss such a mundane thing as your wardrobe, but you’d be wrong.
In 1981, the screen legend sat down with the late Barbara Walters, who asked her about her (groundbreaking for the time) insistence on wearing pants asking, “Do you ever wear a skirt?” Luckily the legendary star wasn’t having it. She coldly quipped, "I have one...I'll wear it to your funeral." Ouch!
When Ellen Made Fun of Taylor Swift’s Dating History
Taylor Swift’s dating history is almost as newsworthy as her music career. Like most of us, however, she would rather not talk about her famous exes. Unfortunately, Ellen DeGeneres didn’t give her a choice.
During their interview, Ellen projected images of Taylor’s exes on a massive screen, basically implying that she had dated many men. Though a visibly-uncomfortable Taylor told the host, “I don’t know if I’m going to do this'” in regards to rehashing her past relationships, Ellen said, “yeah, you will.” Talk about awkward!
When David Letterman Made Paris Hilton Rehash Her Darkest Moment
There are some moments that most people would prefer to forget. Moments like going to jail for example. Unfortunately for celebrity Paris Hilton, David Letterman wasn’t going to let her off that easily. Though their interview began pretty casually (talking about different cities), David began asking the socialite about her 2007 stint in jail.
A visibly uncomfortable Paris initially answered David’s relentless questioning before telling him she would prefer not to talk about it since she’s moved on — a hint she hoped the host would take.
David Letterman’s Creepy Camera Crew
Jennifer Lopez is known for her sensual and trend-setting style, but even the most self-confident person has boundaries. During a particularly uncomfortable interview with David Letterman, JLo was treated like an object when his camera crew zoomed in on her chest.
To make matters more inappropriate, the host referred to her bosom as “pretty darn good.” Jennifer looked clearly uncomfortable as she tried to cross her arms and block the camera’s (and the host’s) view. The whole segment just made us feel gross! We can’t imagine how the star must have felt!
Rihanna Immediately Shuts Down Nosy Reporter
Rihanna has had countless singles top the music charts and she also has a successful clothing and cosmetics company. She's one of the wealthiest women in the world, but she's still subjected to the same tired questions.
While on the red carpet promoting her men’s fragrance, “Rogue:Man”, the singer was asked, “What are you looking for in a man now?” Never one to bite her tongue, the star snapped, “I’m not looking for a man. Let’s start there.” Yas queen! The reporter deserves the cheeky response for asking such a rude question.
Robert Downey Jr. Walked Out of the Interview
“Iron Man” star Robert Downey Jr. has never been shy about his personal battles with substance abuse and his often strained relationship with his father. That said, the actor has enjoyed a career renaissance.
Unfortunately, an uncomfortable interview threatened to take him back to his dark times. Instead of talking about the film, this interviewer wanted to talk about RDJ’s struggles, something the actor didn’t want to take part in. Frustrated, the actor simply walked out. To be honest, we don’t blame him.
When Serena Williams Hit Back
Serena Williams may be one of the greatest athletes in the world, but even she gets tired of being asked obnoxious questions. At a press junket following her win at the US Open, the tennis player was asked why she didn’t have a smile on her face (a question women get asked routinely).
After some uncomfortable prodding from the reporter, Serena finally explained that “to be perfectly honest, I don’t want to be here. I just want to be in bed right now.” We’re sure this wasn’t the answer the reporter was fishing for!
Ellen and Sofía’s Daytime Drama
It’s no surprise that comedian Ellen DeGeneres has many people divided. According to many, her 2017 interview with “Modern Family” actress Sofía Vergara was just one of many times she's shown her true colors. In the interview, Ellen poked fun at Sofía’s accent and English language skills as she attempted to teach the “America’s Got Talent” judge new words in English.
Viewers watched as Sofía awkwardly agreed and said, “Okay, I know English”. Ellen chose very challenging words like “flabbergasted” and “discombobulated”. While Sofía says she was in on the joke, many felt it was insensitive.
Jacob Elordi and Simone Ashley’s Formula 1 Faux Pas
With so many events and interviews to participate in, we can understand why some actors feel pressed for time. That said, getting the chance to be interviewed by the famous British Formula 1 commentator, Martin Brundle, is an opportunity most people attending the Monaco Grand Prix would jump at.
Unfortunately at the 2022 event, “Euphoria” star Jacob Elordi and “Bridgerton” star Simone Ashley awkwardly refused to talk to the famed television icon, with the latter's publicist saying “she doesn’t want to do any tv”. Umm…did she know who she was talking to?
Marky Mark Missed the Mark With His Graham Norton Interview
As one of the most beloved talk show hosts in the UK, Graham Norton has interviewed multiple celebrities. None of that experience, however, could have prepared him for an inebriated Mark Wahlberg as a guest.
The boozed-up actor not only kept interrupting fellow guests but at one point actually sat on Graham’s lap and groped him! The host called the whole incident “annoying” but understood that his behavior was due to jet lag and having too many adult beverages. Hmmm…
Jimmy Kimmel’s Awkward Excuse
Who hasn't used a lame excuse to get out of going somewhere they didn’t want to go? While our little white lies wouldn’t get called out on national television, the same can’t be said about Jimmy Kimmel and Tyler Perry. It turns out that the director invited Jimmy to his big party — an event Jimmy apparently promised to attend but didn’t.
Viewers watched as the host tried miserably to come up with excuses as to why he was a no-show — excuses that were promptly called out by the party-throwing “Madea” star. Should’ve just RSVP’d “no” Jimmy!
Lindsay Lohan’s Intense Grilling by David Letterman
Though many celebrity interviews may seem unplanned or even unfiltered, most interviews are told to stick to publicist-approved questions or topics when questioning their subjects. David Letterman apparently didn’t get the memo.
When interviewing actress Lindsay Lohan, the famed late-night talk show host began bombarding her with questions related to her past struggles with substance abuse and her repeated trips to rehab. Lindsay had to awkwardly sit and try to handle the intense questions before telling the host, “we didn’t discuss this in the pre-interview.” So uncomfortable!
Scarlett Johansson Refuses to Discuss Her Black Widow Wardrobe
When it comes to promoting a film, actors are often asked strange questions about their characters. But asking what her character Black Widow wears under her costume was a bit too much for actress Scarlett Johansson. An interviewer asked if she wore underwear while in costume as the Marvel character.
Annoyed, the actress said, "You're like the fifth person that's asked me that today," she then added, "What is going on? Since when do people start asking each other in interviews about their underwear?" She’s right though. Her costume, her business!
Justin’s Revealing Photos Shown by Ellen DeGeneres
Though they may live in the public eye, celebrities still deserve privacy. In 2015, paparazzi caught singer Justin Bieber in his birthday suit while vacationing in Bora Bora. The star thought those embarrassing pictures were a thing of the past.
Unfortunately while on “The Ellen DeGeneres Show”, she felt the need to not only say “let’s talk about the paparazzi shot in Bora Bora,” but she also projected the embarrassing images on a huge screen to her audience and millions of viewers. Deeply inappropriate! Justin looked visibly uncomfortable.
When Cara Delevingne Was Told to Take a Nap on Television
Model-turned-actress Cara Delevingne is known for her bold personality, but the friction between the Brit and the cast of “Good Morning Sacramento” was just plain uncomfortable.
The star was promoting her film “Paper Towns” on the morning news show when the anchor told her that she seemed “a bit irritated” before telling her, “we’ll let you go take a little nap, maybe get a Red Bull. How ‘bout that.” Cara’s shocked face said it all! It’s probably the last time she agreed to be interviewed by them!
Oprah’s Deeply Personal Questions for the Olsen Twins
From movies to their own fashion lines, Mary-Kate and Ashley Olsen seemed to be everywhere. But by the early 2000s, the twins were making headlines because of their figures — something Oprah felt the need to touch on during her famous sit-down with them.
Viewers could see that they didn’t want to discuss their weight, yet Oprah kept bringing it up. At one point she even asked them, “what size are you, by the way?” — a question many felt was insensitive considering that the twins were already struggling with the media attention.
Matt Lauer’s Inappropriate Questions to Anne Hathaway
Anne Hathaway is not only a very talented actress but she is also known for her bubbly and sweet personality. It’s this easygoing personality that probably allowed her to remain calm during “The Today Show”’s former host Matt Lauer’s tasteless comments.
Though she was there to promote her film “Les Misérables ”, Lauer immediately began asking about her recent red carpet wardrobe malfunction, even making cringe-inducing comments like, “nice to see you. Seen a lot of you lately,” and “what’s the lesson learned from something like that.” Truly unbelievable!
Daniel Craig’s Icy Response
Though it is one of the oldest action-movie franchises, fans still get a bit excited when they hear about a new James Bond film. Unfortunately, the star of the James Bond film “No Time to Die” Daniel Craig didn’t quite share that enthusiasm.
In an uncomfortable red-carpet interview, the actor seemed quite bored and curt. When asked if he’d return for a sequel, he said, “Nope. Definitely not.” And when asked who would replace him as the world-famous spy, he rudely said, “not my problem,”. Umm…tell us how you really feel Daniel!
Jerry Seinfeld Does NOT Appreciate Being Told He Was Canceled
It’s no surprise Jerry Seinfeld ties his self-worth to the immense success of his show “Seinfeld”. So when the late Larry King implied the show had been canceled, he got visibly upset and even raised his voice to ask “Do you know who I am?”
He even questioned if Larry kept up with the news because the show had clearly been a great success. His overreaction resulted in the host trying to get him to calm down. The tension between the two was so strong it was almost palpable.
Bill Murray’s Clumsy Television Appearance
When it comes to giving interviews, actor Bill Murray isn’t usually the biggest fan. It turns out that he might have had to ingest a few adult beverages in order to deal with them. While appearing on MSNBC’s “The Last Word with Lawrence O’Donnell”, the “Lost in Translation” star seemed to be quite inebriated.
In addition to looking a bit “off” and slurring his words, at one point the veteran actor actually fell off of his chair! Perhaps he should put down the bottle before going on television?
Tyra Banks Shows Us She’s #TeamEdward
Remember "The Tyra Banks Show"? The inventor of "smize" decided to add a daytime talk show host to her resume with her very own talk show. In typical Tyra fashion, things got a bit weird, especially when she invited "Twilight" star, Robert Pattinson.
Speaking in a ridiculous British accent, she demanded that Robert bit her neck (like his vampire character does in the films). Feeling too awkward to say no, Robert leaned forward and bit the host in a scene that even the most diehard Twihards (superfans) cringed while watching.
Jennifer Aniston’s Icky Interview
Having been an actress for decades, it’s safe to say that Jennifer Aniston has gone through her fair share of interviews. That said, we don’t think anything could have prepared her for this truly confusing interview with David Letterman.
At some point during the interview, things got a bit hairy between the “Friends” star and the host when he decided to get up close and personal with Jennifer. After breathing into her neck, he then put a lock of hair in his mouth! We really don’t know how she sat through the rest of that interview!
Simone Biles Hits Back at the Most Annoying Question
It seems that being one of the most decorated athletes and a trailblazer in women’s sports isn’t enough to protect you from the dreaded question so many women receive, “why don’t you smile?”
In 2017, while competing in the dance reality competition, “Dancing With the Stars”, Olympic gold-winning gymnast Simone Biles was asked why she wasn’t smiling more. Her (priceless) answer to that completely unnecessary question? “Smiling doesn’t win you gold medals.” Someone give this woman a medal for calling people out!
Dakota Johnson Calls Out Ellen DeGeneres
It's an unfortunate truth that talk show hosts will say anything to add interest to a conversation with a famous guest, even if it means resorting to lying. In an interview with Ellen DeGeneres, the host tried to accuse the “50 Shades of Grey” star of not inviting her to a party.
Dakota was not having it. She snapped, “Actually, no, that’s not the truth Ellen. You were invited.” After Ellen tried to play dumb, Dakota even told her to ask her producer who could verify!
Ellen Dares to Criticize a Diva’s Child
With such a legendary career, we’re not sure how Ellen DeGeneres’s interview with music icon Celine Dion reached the point where they were talking about the length of Celine’s son’s hair.
Apparently, the singer had a problem with comments about his long hair, especially after Ellen asked, “When are you going to cut that hair?” The singer then asked if the host had a problem with it before Ellen changed the subject and ended that very weird exchange. As a host, she should know that children are a touchy subject for most parents!
When an Interviewer Tried to Body-Shame Helen Mirren
Considered one of the most celebrated actresses in film, Dame Helen Mirren has been acting for decades. But in a 1975 interview, her incredible talent was questioned by a reporter who rudely asked the legend, “Do you find that your figure,your physical attributes, hinder you in your pursuit of the ambition of being a successful actress?”
Ever the strong woman, Helen replied that she hoped her performance and relationship with her audience would “overcome such boring questions”. Amen!
Tyra Banks and Naomi Cambell’s Epic Feud
Some celebrities feel that if they air their dirty laundry, it’ll help them find closure. Perhaps that’s what former model Tyra Banks thought would happen when she brought rival supermodel Naomi Cambell onto her talk show in 2005.
Unfortunately, Naomi basically denied any wrongdoing or said she couldn’t remember any of the events and at one point implied Tyra was lying about Naomi trying to sabotage her modeling career. As predicted, the disastrous interview didn't bring the two fashion icons any closer, and the two are still feuding!
50 Shades of Awkwardness Between Dakota Johnson and Melanie Griffith
Just like many of us have awkward interactions with our families, so do celebrities. The only difference is that those uncomfortable moments often play out in front of worldwide audiences.
At the 2015 Oscars, tensions rose between actress Dakota Johnson and mother Melanie Griffith when the conversation turned to Dakota’s role in the risque film, “50 Shades of Grey”. Melanie clearly didn’t want to see the film (understandable), but Dakota seemed to insist. The poor interviewer just felt like she was in the middle of a Hollywood-style family feud!
Vin Diesel’s “Fast & Flirty” Side
In the “Fast & Furious” films, Vin Diesel has no problem speeding, but many wished the actor would’ve pumped the brakes during his wildly uncomfortable interview with Brazilian YouTube star Carol Moreira. The actor made us all cringe with his overt flirting and focus on the interviewer’s looks.
At one point he even asked, “How am I supposed to do this interview? Look at this woman. She’s so beautiful. Talk to me, baby.” Ugh! He even said she was “too sexy” for him to continue the interview, which Moreira said made her feel “completely uncomfortable.”
Taylor Swift’s Icy Response About Her Love Life
When you’re a young star with a penchant for singing about your famous exes, it’s only natural that the world would have questions about your love life. While on the Grammys red carpet, the singer was approached by reporters who joked, “you’re gonna walk home with more than just a trophy tonight. I think lots of men.”
A comment to which Taylor retorted, “I’m not gonna walk home with any men tonight. I’m gonna go hang out with my friends and then I go home to the cats.” Way to overspeculate!
James Brown’s Jaw-Droppingly Bizarre Interview
While James Brown is often considered the “godfather of soul”, the famous musician had a dark side. By the late ‘80s, he had been charged with various serious crimes. For some reason, in 1988, he decided to discuss the criminal investigation against him on CNN.
What ensued was truly disturbing. The singer would reply to serious questions by breaking out into song or responding using song lyrics. Many believed that James was under the influence of some pretty potent substances during the interview, and it’s not hard to see why.
Ariana Grande Calls Out DJ for Ridiculous Question
It's no secret that men and women are often treated differently, especially when they’re in the public eye. While dropping in at the radio station Power 106 FM, the “Positions” singer was asked a very strange question.
The DJ asked her, “If you could use your makeup or your phone one last time, which one would you pick?” The ridiculous question resulted in the shocked star answering, “Is this what you think girls have trouble choosing between?” We hope her response caused him to rethink his stereotypical questions for future guests.
David Letterman Gets Touchy With Catherine Zeta-Jones
Catherine Zeta-Jones is one of the most talented women in Hollywood. Though she usually maintains an effortlessly cool and elegant composure, even she seemed physically uncomfortable when interviewer David Letterman randomly touched her hair.
The non-consensual touching of the hair was not only awkward but also very unnecessary. We can’t imagine him doing that to one of his male guests.
Selena Gomez Makes a Hasty Exit After Reporter’s Question
We’ve all had moments when we’ve wanted to disappear rather than answer an uncomfortable question. But in 2013, while promoting her album “Stars Dance”, Selena Gomez decided to literally disappear (off the screen) during a satellite interview with WGN Chicago after being asked about her tumultuous relationship with Justin Bieber.
Sure, she could have blamed it on a technical malfunction, but most viewers knew that she intentionally ended the interview rather than face the music, or rather judgemental comments about her ex-beau!
Ellen’s Crude Comment Gets Lost in Translation
When interviewing someone from another country or culture, it’s important to understand the cultural differences regarding different topics such as dating and relationships — something talk show host Ellen DeGeneres learned the hard way.
During an interview, the host decided to ask Korean pop group BTS if they had ever “gotten together” or “hooked up” with their fans. When she was met with silence, she asked the band’s translator to translate her way-too-personal question, making the seemingly-conservative translator and the boy band members deeply uncomfortable.
Britney’s Bikini Clad Appearance on David Letterman
There are some ideas that television writers come up with that in reality should never see the light of day, and this was one of them. For some reason, late-night host David Letterman decided to have pop star Britney Spears present a list called “Top Ten Ways the World Would Be Different if Britney Spears Were President” … all while wearing just a bikini.
Considering the star’s struggles with mental health and substance abuse, the whole segment just felt exploitative and uncomfortable, not to mention David poking fun at her intelligence. Just mean!
When Wendy Williams Tried to Shame Draya Michele
Some viewers turn to the Wendy Williams show because they appreciate Williams’s in-your-face personality and candid style of interacting with her guests. Known as a “shock jockette” for her bold interview style, she usually knows how to get the scoop. Unfortunately, that can often mean crossing the line.
When interviewing “Basketball Wives” reality star Draya Michele, the host asked Draya, “How many basketball players have you been with?” before justifying her question by adding “this girl has gotten around.” To say we were stunned would be an understatement!
Meg Ryan Tells Interviewer to “Wrap It Up”
Meg Ryan may have been called “America’s Sweetheart” thanks to appearing in many classic rom-coms, but the actress was anything but sweet during her infamous interview with journalist Sir Michael Parkinson.
During the awkward interview, Michael made rude comments about Meg’s nude scene in the film “The Cut” and even questioned her commitment to the craft of acting! The strange exchange prompted Meg to refer to Sir Michael Parkinson as a “nut” and compare his criticism to a “disapproving dad.” No wonder she suggested that they “just wrap it up”!
Paula Abdul’s Puzzling Interview
While many interviews are made awkward because of a reporter or host’s behavior, it is sometimes the strange antics of a celebrity that make an interview go south. While appearing on the Seattle-based Q13 Fox Morning News, Paula’s behavior began to confuse the news anchors and viewers alike.
From giggling profusely to slurring her words, it became obvious to many that the “American Idol” judge may have taken something to alter her behavior. Though Paula tried to blame it on technical issues, many thought that was a “Straight Up” lie!
Ben Affleck’s Bad Behavior
In case the universally-panned film “Jersey Girl” wasn’t bad enough, the publicity for the film was just as awful. During an interview with French-Canadian journalist and host of the entertainment show “Box-office”, Anne-Marie Losique, Ben Affleck was on his worst behavior.
As Anne-Marie sat in his lap (!), the “Gone Girl” star had his arms wrapped around her. To make matters even worse (and more uncomfortable), he apparently suggested that she remove her shirt, commented on her physical attributes, and made fun of french accents. What a faux pas!
Tom Cruise’s Infamous “Glib” Interview
It seems that no list of awkward celebrity interviews would be complete without a mention of Tom Cruise’s 2005 interview with Matt Lauer. During the interview, the “Top Gun” actor decided to go on a rant about antidepressants and other prescription medications.
As Tom continued his passionate rant, host Matt Lauer sat there stunned before trying to bring a bit of nuance to the controversial debate. Unfortunately, his attempts to offer another perspective get him labeled “glib” by the actor in this now infamous interview!
Brooke Shields’ Painfully Inappropriate Interview
During the early ‘80s, Brooke Shields was one of the most famous faces, especially because of her infamous advertisement for Calvin Klein jeans, where the then-15-year-old provocatively asks viewers, “You want to know what comes between me and my Calvins? Nothing.”
The controversial ad led to the young star being interviewed by the late veteran journalist Barbara Walters. What made this interview uncomfortably awkward were the inappropriate questions Barbara aimed at the young teen about her body and love life. Brooke later called the whole ordeal “practically criminal” and we don’t blame her!