There’s been a long history of awkward interviews, but some cross way past the line of awkward and land straight in the territory of inappropriate. Looking back, it’s surprising how normal it all seemed at the time.
In the moment, these interviews aired on national television, got picked up by magazines, and were treated like just another part of the celebrity machine. But when you step back, you start to realize just how weird a lot of it was.
And not weird in a funny way, weird in a why-would-you-ask-that kind of way. Especially when you remember that a lot of these celebrities were still teenagers at the time.
1. A Red Carpet Reporter Asked 15-Year-Old Justin Bieber To Explain The Sex Talk
During a red carpet interview at the Grammys, a female reporter asked 15-year-old Bieber to give her the sex talk. He handled it smoothly, calling out how odd the request was and quickly shifting the conversation.
Reporter: Has your mom given you a sex talk yet?
Bieber: I mean, I really don’t want to have that conversation with my mother. I’ve kind of had it with my father.
Reporter: Oh really? See my parents never gave me the sex talk.
Bieber: Okay.
Reporter: My parents never gave me the sex talk… So why don’t you give me the sex talk?
Bieber: I really- I feel uncomfortable right now.
Reporter: Aww!
Bieber: Why do want to know the sex talk from a 15 year old boy? That’s pretty weird. Let’s talk about the album.
2. Sabrina Carpenter Was Asked About Sexting
The hosts of The Zach Sang Show appeared caught off guard when they found out Sabrina Carpenter was only 17, leading co-host Dan Zolot to blurt out, “Da*n! You’re so young!” That didn’t stop them from continuing with the questions that followed.
Zolot: Are you into sexting?
Carpenter: Yeah, no, I’m still in the teenage phase where it’s weird if I send the first text.
Zolot: Yeah but what if somebody sexts you first, do you respond?
Carpenter: Actually, that’s the reason I deleted Snapchat in the first place… I just created one a month ago, but I was getting bad things…
Sang: See, I want bad things. It’s like an ego boost… I’ll welcome any nude.
3. Ivo Niehe Bluntly Asked 17-Year-Old Britney Spears About Her Breasts
During a 1999 appearance on the Dutch TROS TV program, 17-year-old Britney Spears was directly asked by host Ivo Niehe to talk about her breasts. The exchange was uncomfortable on its own, even without factoring in her age.
Niehe: In the video we just saw, “Baby One More Time,” you’re the naughtiest of schoolgirls aren’t you?… But in reality you’re not?
Spears: Well of course my school’s not like that, I wish it was, I wish we could be dancing in the hallways and stuff like that…
Niehe: There’s one subject we didn’t discuss. What was that? Everyone’s talking about it.
Spears: What?
Niehe: Well, your breasts.
Spears: [awkward laughing] My breasts?
Niehe: Well, you seem to get furious when a talk show host comes up with this subject. In general, what do you think about breast implants?…
Spears: I think if that’s what you want to do, if that’s what would make you happy, then I see nothing wrong with it. But I haven’t done that.
4. The Women Of ‘The Talk’ Seemed To Forget The Age Of Guest Justin Bieber
Justin Bieber was a guest on the first season of The Talk, where he sat down with hosts Julie Chen, Sara Gilbert, Sharon Osbourne, Leah Remini, Holly Robinson Peete, and Marissa Jaret Winokur. Clips from the episode later resurfaced on TikTok, showing some uncomfortable moments, including Leah Remini repeatedly reaching toward Bieber and asking him awkward “would you rather” questions.
Remini: Would you rather have to be naked on stage during one full song, or drink a cup of blended worms? Answer Justin Bieber!
Bieber: I have like, little girl fans, I can’t go-
Remini: Imagine there was no laws…
Robinson Peete also delved into his aspirations for marriage and children:
Robinson Peete: What age would you want to get married and how many kids would you want to have?
Bieber: So, I’m like, 17, so…
Robinson Peete: 17 kids?!
Meanwhile, Chen put the teen idol on the spot and asked him of the five adult hosts:
If you had to date one of us five, who would it be?
5. Oprah Winfrey Wanted To Know The Olsen Twins’ Size
In 2004, the 17-year-old Olsen twins appeared on The Oprah Winfrey Show. During the interview, Oprah brought up recent tabloid rumors about Mary-Kate Olsen and an alleged eating disorder. Ashley Olsen jumped in to respond for her sister.
Winfrey: I know a new rumor that’s recently surfaced has really upset you, right? You know, the one about eating.
Ashley Olsen: Yeah, you know people are gonna write what they’re gonna write. We try not to read the good or the bad because it just comes with the territory. Either you’re too fat, too skinny and people are just gonna write what they-
Winfrey: What size are you, by the way?
Ashley Olsen: Size?
Winfrey: Yeah, I would really like to know-
Ashley Olsen: I’m really short?
Winfrey: Oh, you’re not sure?
Mary-Kate Olsen: We’re petite girls-
Winfrey: [sarcastically] Ohh that’s so interesting.
6. Teenaged Britney Spears Was Repeatedly Asked About Her Virginity
The media had a long-running fixation on Britney Spears’s virginity, starting when she first became famous as a teen and continuing through her relationship with Justin Timberlake. Even after she publicly said she planned to wait until marriage, the questions didn’t stop. In one interview in Norway when she was 18, the topic came up yet again.
Interviewer: You’re not going to have sex before your marriage. Is that a standard that is hard to live up to?
Spears: No, not at all. I mean, I’m 18 and I have so much of my life to look forward to… I just want to make sure that the person that I do that with is the right one… I’m so busy focused on my career and focused on me.
7. Ellen DeGeneres Showed Justin Bieber’s Nude Paparazzi Photos On Screen
During an interview on The Ellen Show, Ellen DeGeneres showed a censored version of a recently published paparazzi photo of Justin Bieber and asked the 19-year-old about it.
DeGeneres: Speaking of you in your underwear let’s talk about the paparazzi shot in Bora Bora… Usually we’re all pretty good at spotting paparazzi… How did you not see that there was paparazzi there?
Bieber: I just didn’t see them, I think I wasn’t really looking out for them either.
8. Barbara Walters Asked 15-Year-Old Brooke Shields About Her Measurements
As a child star, Brooke Shields had already dealt with being sexualized by adults, especially after her roles in Pretty Baby and Blue Lagoon. At 15, she appeared in a Calvin Klein ad with the line, “You want to know what comes between me and my Calvins? Nothing,” which she later said she didn’t fully understand at the time. Not long after, she sat down for an interview with Barbara Walters.
Walters: Brooke, what are your measurements?
Shields: Um, I’m 5’10” and 120.
Walters: Would you be a mother like your mother?
Shields: I think so, yes…
Walters: But what about the people who say ‘She had no childhood’?…
Shields: But I’m still going through my childhood so I can’t say that I didn’t.
Walters: Sitting here like this is going through your childhood?
Shields: …I enjoy this…
Walters: Do you have any secrets from your mother?
9. David Letterman Repeatedly Questioned Miley Cyrus On Her ‘Lost’ Youth
When 17-year-old Miley Cyrus appeared on Letterman, the host focused on her age and kept pointing out that she wasn’t like a typical teenager.
Letterman: Our first guest is 17 years old… I think of you as a kid but you’re more than a kid. But you are a kid, right?
Cyrus: Yes.
Letterman: So tell me some kid things that you do. Has the kid part of you gone, or is it still there?
Cyrus: Um, no I’m still a kid… anyone that says she’s growing up too quick doesn’t know me personally…
Letterman: Just sitting here talking to you, you don’t seem like a normal 17 year old… You’ve grown up.
Cyrus: Well I think-
Letterman: One wonders… Anything you miss about a childhood that you lost? Have you lost a childhood?
Cyrus: I don’t think so. I’ve gone through awesome things and I’ve gotten to perform and do what I love, so for me that’s what I’ve always wanted to do.
Letterman: Are you looking for the warmth the spotlight can’t provide?
