14 Inappropriate Celebrity Interview Moments From The 1990s

This post contains mention of eating disorders and sexual assault.

In the heyday of shock jocks and tabloids, celebrity interviewers sometimes chose invasive and inappropriate questions over basic manners or human decency.

Here are 14 celeb interview moments from the '90s that did NOT age well:

1.Two months after Victoria Beckham gave birth to her first son, Brooklyn, in 1999, TFI Friday presenter Chris Evans (no, not that Chris Evans) made her weigh herself live on air to prove she was back to her pre-pregnancy weight.

In 2022, she told Vogue Australia, "I'd just had Brooklyn and lost a lot of weight after...He made me stand on the scales to be weighed. Can you imagine doing that nowadays?!"

Watch the full clip below, with this part starting at the 3:23 mark:

2.As Victoria mentioned, Chris Evans also made her former fellow Spice Girl, Geri Halliwell-Horner, step on a scale earlier that year.

Here's the full clip, with this part starting at the 4:38 mark:

3.When 17-year-old Alicia Silverstone appeared on The Jon Stewart Show in 1994, the host asked her age and then referenced Joey Buttafuoco, who was charged with statutory rape in the infamous "Long Island Lolita" case.

Here's the full clip, with this part starting at the 0:39 mark:

4.When seven-year-old Mara Wilson attended the Nine Months premiere in 1995, "a red carpet reporter [asked her] opinion about Hugh Grant getting busted for prostitution."

In an article she wrote for Cracked, Mara continued, "If he had been arrested for something like defacing a Lion King poster or stealing bouncy castles, I might have cared. But while I knew he'd been arrested, I didn't understand what for and didn't feel comfortable answering. My father called the station the next day to suggest that they, you know, not talk to a child about soliciting sex. But he was rebuffed, and the complaint was ignored. Even then, as a kid, I knew that parental power was gone."

5.In 1998, Howard Stern kept asking Mariah Carey if she was wearing underwear or not.

Here's the full clip, with this part starting at the 6:24 mark:

6.On the 1999 Academy Awards red carpet, Joan Rivers brought up rumors that Mariah Carey had gained weight, but the singer just brushed her comments off.

Watch the full clip below, with this part starting at the 0:43 mark:

7.When Fran Drescher appeared on The Howard Stern Show in 1994, the host asked about when she was raped, made jokes about it, and continually asked about the race of the rapists and their victims.

The full interview — which mentions sexual assault and violence — is below, with this part starting at the 8:16 mark:

8.When 17-year-old Britney Spears appeared on The Rosie O'Donnell Show in 1999, Rosie lectured her about a wardrobe malfunction she experienced at the Kids' Choice Awards.

Here's the full clip, with this part starting at the mark:

9.Also in 1999, TROS TV host Ivo Niehe asked Britney Spears about rumors she had breast implants because "everyone's talking about it" and showed a newspaper article speculating about the rumors.

Here's the full clip, with this part starting at the 6:17 mark:

10.In 1997, MTV News reporter Tabitha Soren confronted Lauryn Hill about pregnancy rumors and then asked if her baby was "planned."

Here's the full clip, with this part starting at the 0:07 mark:

11.In 1996, Oprah Winfrey asked Nathan Lane — who wasn't ready to publicly come out at the time — if he was afraid his The Birdcage role would lead to rumors about his sexuality. Sensing his discomfort, his costar Robin Williams made a joke to change the conversation.

On a 2023 episode of Sunday Sitdown with Willie Geist, Nathan said, "I don't think Oprah was trying to out me, but I said to Robin beforehand: 'I'm not prepared. I'm so scared of going out there and talking to Oprah. I'm not prepared to discuss that I'm gay on national television, I'm not ready.' And [Robin] said, 'Oh, it's alright, don't worry about it, we don't have to talk about it, we won't talk about it.'"

Here's the full clip:

Harpo Productions / NBC

12.In 1994, David Letterman tried to goad Madonna into kissing a random member of the studio audience.

Watch the full clip below, with this part starting at the 0:12 mark:

13.In 1993, Oprah Winfrey asked Michael Jackson if he was a virgin, and when he expressed discomfort with the question, she continued to pressure him to give an answer.

Watch the full clip below:

14.And finally, when Jennifer Aniston appeared on the Late Show with David Letterman in 1998, the host put a piece of her hair in his mouth — then got her to apologize for screaming.

Here's the full clip:

CBS / Via x.com

If you or someone you know has experienced sexual assault, you can call the National Sexual Assault Hotline at 1-800-656-HOPE, which routes the caller to their nearest sexual assault service provider. You can also search for your local center here. 

The National Eating Disorders Association helpline is 1-800-931-2237; for 24/7 crisis support, text “NEDA” to 741741.