Warning: This post mentions eating disorders.
Looking back at old talk shows and publications, some of the questions that interviews thought were appropriate to ask celebrities — mostly young women — are unbelievable.
Here are 13 wild and inappropriate questions I cannot believe interviewers had the audacity to ask celebs in the '00s:
1. In 2003, Diane Sawyer asked Britney Spears about losing her virginity and what she'd tell her then-12-year-old little sister, Jamie Lynn, about sex before marriage.
Watch the full interview below, with this part starting at the 27:57 mark:
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2. In a 2002 TV interview, Connie Chung reportedly asked then-16-year-old Mary-Kate and Ashley Olsen if they were virgins. Ashley "was like, 'That's personal. Why would you be asking a 16-year-old that question in the first place?'"
Reflecting a year later, Ashley told Rolling Stone, "I got really angry and defensive."
3. In 2004, Oprah spoke to Mary-Kate and Ashley Olsen about rumors they both had eating disorders. In response, they said that they tried "not to read the good or the bad" things about themselves in the press, and then the host abruptly changed the subject to their clothing sizes.
4. At the 2007 Virgin Fest, a MUCH interviewer asked Alex Turner and Jamie Cook of the Arctic Monkeys a sexual question about their famous peers — which they basically refused to answer.
Watch the full clip below, with this part happening at the 3:36 mark:
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5. In 2004, a panel of news anchors kept asking Janet Jackson about her recent wardrobe malfunction during the Super Bowl halftime show. However, her Why Did I Get Married? costar Tyler Perry answered for her, redirecting the conversation to their movie.
Watch the full clip below, with this part begining at the 2:04 mark:
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6. When Leighton Meester appeared on Ellen in 2009, she seemingly tried to avoid talking about part of her childhood, but the host blurted it out.
Here's the full clip, with this part starting at the 0:58 mark:
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7. In 2007, David Letterman turned an interview that was supposed to be about Paris Hilton's new perfume into one about her and Nicole Richie's recent experiences in jail.
On a 2021 episode of her podcast This Is Paris, she said, "That was off limits and he would not discuss it, and we would only be there to promote the perfume and my other business ventures. I felt like it was a safe place because I'd been going on Letterman for so many years. He'd always have fun with me and joke around, but I thought he would keep his word on this and I was wrong."
Watch the full clip below, with this part starting at the 0:43 mark:
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8. When Emma Watson appeared on the Late Show with David Letterman in 2009, he held up a picture of her recent wardrobe malfunction and made her address it in front of a live studio audience.
You can see the full clip at the 0:13 mark below:
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9. In 2008, Ellen brought up rumors that Mariah Carey was pregnant and then pressured her to drink to prove they weren't true, essentially forcing her to announce her pregnancy.
In 2020, Mariah told Vulture, "I was extremely uncomfortable with that moment is all I can say. And I really have had a hard time grappling with the aftermath. I wasn't ready to tell anyone because I had had a miscarriage...I didn't enjoy that moment."
Watch the full clip below:
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10. When the Advocate interviewed Anne Heche in 2001, the interviewer asked if her then-husband, Coleman Laffoon, had "a same-sex experience in his past that would have left him open to a broader worldview." She replied, "One, that's none of my business or your business to even ask that question, and it's completely out of line."
The interviewer tried to apologize, but Anne continued, "This is not an article about Coley...I'm finished with this conversation. You have got to be kidding me, after everything I have given you, you are now asking me about my husband's sexuality? That is flooring to me."
11. In 2005, Howard Stern asked Emma Bunton about rumors David Beckham was cheating on her former Spice Girls bandmate, Victoria Beckham. Then, he told her she'd have to take off her clothes if she didn't answer.
Here's the full clip, with this part starting at the 13:20 mark:
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12. In 2002, Howard Stern and his coworkers tried to take bets on how much Anna Nicole Smith weighed and get her to step on a scale live on air.
Here is the full interview, with this part beginning around the 24:10 mark:
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13. And finally, when Anderson Cooper interviewed Lady Gaga on 60 Minutes Overtime in 2009, he brought up rumors that she had a penis and questioned why she didn't confirm or deny them.
Here's the full clip:
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The National Alliance on Mental Illness helpline is 1-888-950-6264 (NAMI) and provides information and referral services; GoodTherapy.org is an association of mental health professionals from more than 25 countries who support efforts to reduce harm in therapy.
The National Eating Disorders Association helpline is 1-800-931-2237; for 24/7 crisis support, text “NEDA” to 741741.
EXmas, starring Leighton Meester and Robbie Amell, is streaming now for free on Freevee.
