Sexist and Offensive Celebrity Interviews – PopCrush

For decades, female celebrities have been subjected to levels of criticism, judgment and downright gross questioning that their male counterparts have rarely had to endure. "Would you be asking that question if I were a man?" has become a refrain often spoken again… and again… and again over the course of many women entertainers' careers.
From Britney Spears to Paris Hilton, Taylor Swift, Ariana Grande and more, we as a society have all too often reveled in the offensive narratives the media has painted of the It Girls we claim to adore. Sadly, this penchant for sexism is most often on display in the celebrity interview. (And no one — and we mean no one  in the modern age of the female superstar has gotten more of it than our beloved Spears.)
And in case you're wondering, it's not just male journalists asking mind-boggling, inappropriate questions of female stars. In fact, there might be more female reporters and talk show hosts providing disheartening examples of terrible journalism on this list than their male counterparts, including more than a couple of high-profile names.
Below, we've rounded up 15 examples of completely sexist interview questions that (hopefully) would get swiftly shut down today. Watch the cringe-worthy moments if you dare, and try not to scream at YouTube while you're at it…
The first interview on this list took place when Britney was just 17 years old, in the wake of releasing her debut album. In fact, Rosie O'Donnell kicks off the chat by calling the then-teenage pop star a "little kid." The outspoken talk show host then proceeds to chide Britney for the white crop top she wore to perform at the Nickelodeon Kids Choice Awards in Orlando.
Right from the beginning of her career, Britney has been subjected to all sorts of inappropriate interview moments, and this moment with Rosie was unfortunately just the start…
In 2007, Paris Hilton was at the height of her legal troubles as one of the most notorious It Girls in all of Hollywood. After spending two controversial weeks in jail that summer for a probation violation, the socialite mounted a comeback tour to promote her new fragrance, Can Can.
As part of the media blitz, she agreed to appear on the Late Show with David Letterman. Ahead of time, the talk show host had agreed to focus on the icon's business venture, but the moment she sat down, he started peppering her with mean-spirited questions about her time behind bars.
"How'd you like being in jail?" he asked a clearly blindsided Paris. At first, she tried to laugh the questions off, but Paris became increasingly and visibly upset the longer the nearly 10-minute interview went on.
"Now you're making me sad that I came because you're hurting my feelings," she finally told Letterman after he rebuffed repeated attempts to change the subject, while the audience laughed at her expense.
Rosie strikes again! Just one year after reprimanding Britney, the talk show host embarrassed Christina Aguilera by calling the dress the Grammy winner wore to the 2000 ceremony — where she took home Best New Artist — "a little risqué, but not trampy in any capacity."
Rosie then went on to pester the pop star about whether or not she was worried about how her clothing choices were affecting little girls idolizing her at home — which is just such a classically judgmental question, we wish Christina hadn't even dignified it with a response.
Rosie O'Donnell isn't the only female talk show host famous for putting her female guests on the spot with inappropriate questions. In 2008, Ellen DeGeneres fully outed Mariah Carey's pregnancy during a live interview on her eponymous show.
After Mimi refused to comment on the rumors, Ellen sprung a champagne toast on her, for all intents and purposes revealing the songstress was likely expecting when she obviously couldn't partake in the bubbly.
There's nothing more downright creepy than watching an older male host ask Britney Spears about her breasts in this interview taken from Dutch program <em>TROS TV</em> when the pop star was still just 17 years old.
"There was one subject we didn't discuss. What was that? Everyone's talking about it," 50-something-year-old Ivo Niehe says to a confused Britney during the chat, who replies with an innocent "What?"
"Well, your breasts," he responds as the audience murmurs and the pop star slowly repeats his words.
After asking Brit about her thoughts on breast implants, she responds diplomatically, saying that if plastic surgery makes someone happy, go for it — while also clarifying that she, a minor, didn't have any work done.
What's perhaps worse is that two decades later, Ivo doubled down and defended his line of questioning after the clip unseen by many Americans was unearthed for The New York Times Presents: Framing Britney Spears.
Anne Hathaway was put on the spot by certified creep (and accused sexual predator) Matt Lauer while promoting the big-screen adaptation of Les Miserables back in 2012.
"Good morning, nice to see you — seen a lot of you lately," the TODAY host said to kick off the interview, alluding to an incident involving a wardrobe malfunction and a photographer that had occurred to Anne just days earlier.
"Sorry about that; I'd be happy to stay home, but…the film," she responded with a polite laugh. However, Lauer went on to press the issue, asking the soon-to-be Oscar winner what she had learned from the moment in which she was taken advantage of.
Naturally, Anne's response was both a master class in on-air decorum and a gracefully-worded mic drop that she quickly tied back to her role as Fantine. Except she shouldn't have had to do any of that in the first place…
Appearing at a press junket with co-star Jeremy Renner to promote The Avengers, Scarlett Johansson didn't take kindly to probing questions about whether she was able to wear underwear with her Black Widow costume.
"You're like the fifth person that's asked me that today," she said to the interviewer. "What is going on? Since when did people start asking each other in interviews about their underwear?"
The host tried to justify his creepy question by claiming he asked because the outfit was "just so skin-tight," but the actress refused to take the bait, simply telling him, "I'll leave it up to your imagination, OK?"
As she says moments later: What kind of an interview is this?
Taylor Swift has always battled the media narrative that she's a boy-crazy serial dater. But at the 2015 Grammys, the superstar put Entertainment Tonight's Nancy O'Dell firmly in her place when the interviewer suggested she'd be going home with both some awards and "lots of men" after instructing the camera to pan to Tay's legs.
"I'm not gonna walk home with any men tonight," a clearly and rightfully annoyed Taylor clapped back. "I'm gonna go hang out with my friends and then I go home to the cats. Men get me in trouble, I don't… no."
Nancy tried to bounce back with a laugh, but the joke was on her because one year later, Taylor returned to the show to take home her second Album of the Year win for 1989.
At the launch event for Rogue Man by Rihanna, the pop star was accosted by a question from a reporter about what she was looking for in a man.
"Pardon?" she asked the female journalist, who then decided to repeat the misguided query.
"I'm not looking for a man, let's start there," RiRi stated with a smirk before walking off. In the immortal words of her 2008 hit "Take a Bow": "You look so dumb right now," indeed.
Are you really surprised there's another Ellen moment on this list? Back in 2012, the "Queen of Nice" made Taylor Swift visibly uncomfortable by prying into her dating life, forcing her to play a game to reveal who she'd written Red lead single "We Are Never Ever Getting Back Together" about.
Standing her ground, an upset Taylor refused to play, and also repeatedly denied Ellen's completely false assertion that she had dated her The Lorax co-star Zac Efron.
"Do you know how badly this makes me feel?" the singer asked.
Ariana Grande was not having it when the DJs at a Los Angeles radio station lobbed an absolutely idiotic and sexist question her way during a live, on-air interview.
"If you could use makeup or your phone one last time, which one would you pick?" the host asked.
"Is this what you think girls have trouble choosing between?" the pop singer asked incredulously, eventually adding, "You need a little brushing up on equality." Thank you, next.
Rihanna brilliantly shot down an inane question about her dating life while attending a press conference overseas to promote her debut starring role in 2012's Battleship.
"Things are clearly going brilliantly in your career. I just wondered if you are as happy in your private life, and will we be seeing a certain Mr. Ashton Kutcher, perhaps, making a trip over here?" the female reporter asked, alluding to the rumors the pair were an item at the time.
"Wow, how disappointing is that question," the then-budding multi-hyphenate responded with an exasperated laugh. "I'm happy and I'm single, if that's what you're really asking."
Lady Gaga's identity was a huge topic of gossip when she burst onto the scene in the late 2000s, and she's always been pretty unbothered by the speculation.
A perfect example recently resurfaced in an old 60 Minutes Overtime interview when Anderson Cooper, whom should really know better, asked Mother Monster point blank about her genitalia.
"There was that rumor that you had a male appendage, that you were a hermaphrodite," he said, to which Gaga nonchalantly replied, "Maybe I do. Would it be so terrible?… Why the hell am I going to waste my time and give a press release about whether or not I have a penis? My fans don't care, and neither do I."
Lady Gaga: 1. Transphobia: 0.
When Ariana Grande first released her debut album Yours Truly in 2013, a minor controversy erupted over the LP's original cover art, which some critics claimed was reminiscent of Lolita.
In a sit-down with major Australia and New Zealand media conglomerate Fairfax Media, the burgeoning pop star hit back at a downright rude Twitter comment about how young she looked.
Adding the caveat that he thought the tweet was "cruel," the interviewer followed it up by asking, "Does it bother you at all that you look so much younger than your age? Because some girls don't like it."
"No," the then-20-year-old singer replied. "I don't really focus too much on that. I think if I did, I would be giving into my ego and then I would be, like, very… not productive. I feel like I wanna spend my time on other things.
"But also," she added, "I'm in this 'cause I like making music, not because I wanna be a supermodel."
Where to even begin with Britney's infamous 2003 interview with Diane Sawyer? There's the fact that the veteran journalist asked the then-21-year-old intimate details of her sex life with ex Justin Timberlake.
Or maybe the way she manipulated the pop star by asking Britney what she would tell her 12-year-old sister Jamie Lynn about losing her virginity before marriage.
Or we could go with Sawyer playing a clip of former first lady of Maryland Kendall Ehrlich claiming, "If I had an opportunity to shoot Britney Spears, I think I would," and then having the audacity to justify the violent statement by saying, "Because of the example for kids and how hard it is to be a parent and keep all of this away from your kids."
Or maybe it's the shaming of Britney's clothing and style choices, and blatant example of "gotcha!" journalism by using her past photo shoots against her. We could go on and on, but needless to say, it's no wonder Britney ended up in tears by the interview's end…

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