16 Gross, Uncomfy, And Inappropriate Celeb Interview Moments From The Last 10 Years

There are a lot of shockingly inappropriate, rude, or invasive celebrity interview questions from decades past. We may like to think we've grown past that as a society, but unfortunately, there are still plenty of moments like this in recent history.

Here are 16 rude and inappropriate celeb interview moments from the last 10 years:

1.When Olivia Rodrigo appeared on Jimmy Kimmel Live in 2023, the host pointed out a hardly noticeable chip in her tooth that she didn't realize was there before, giving her a new insecurity.

Watch the full video below, with this part starting at the 8:10 mark:

2.At the 2015 Grammys, an Entertainment Tonight reporter insisted that Taylor Swift would be getting "lots of men" that night.

Watch the full clip below, with this part starting at the :20 mark:

3.When British GQ interviewed One Direction in 2013, they asked Harry Styles, "Do you know how many people you've slept with?" After he said yes, they kept pressing for the exact number, asking, "Can you give me a rough, ballpark figure? Say 'yes' or 'no.' Less than 100? Lower than 50?"

After a few questions in that direction, Harry said, "I'm not doing this! You're cornering me!"

GQ said, "Come on, you're a rock star. OK, less than 10."

Harry replied, "Yes. Two people. I've only ever had sex with two people."

Then the interviewer said, "I don't believe you."

4.At the 2013 Oscars, an AP red carpet interviewer reportedly refused to try to pronounce 9-year-old Quvenzhané Wallis's name and told her, "I'm just going to call you Annie." She replied, "My name is not Annie. It's Quvenzhané."

5.In 2014, ABC News interviewed 11-year-old Quvenzhané Wallis in a toy store, yet asked a question that insinuated she was no longer a child.

Here's the full interview, with this part starting at the 1:35 mark:

6.When Nick Jonas appeared on The Wendy Williams Show in 2014, she asked him about the purity ring he wore the last time he visited the show.

Here's the full broadcast, with this part starting at the 23:12 mark:

7.Then, in 2018, Wendy Williams told 18-year-old Marcus Scribner that she didn't "want him to date," then asked about his sex life.

Watch the full clip below, with this part starting at the 6:35 mark:

8.Backstage at the 2015 Victoria's Secret Fashion Show, a TMZ reporter asked multiple models what they were looking forward to eating after the show. Magdalena Frackowiak called them out on it.

You can watch the full clip below, starting at the 1:25 mark:

9.At the 2014 MTV Movie Awards, Jamie Lee of The Pete Holmes Show had an infamously awkward red carpet exchange with Shailene Woodley.

Here's the full clip, with this part starting at the 1:40 mark:

10.When BTS appeared on The Ellen DeGeneres Show in 2017, she asked if they'd ever slept with their fans.

Here's the full clip, with this part starting at the 3:20 mark:

11.In 2014, Rolling Stone asked Lana Del Rey, "So, on a scale of 1 to 10, how much do you wish you were dead right now?"

The reporter was referencing a recent interview where Lana told the Guardian, "I wish I was dead already."

To Rolling Stone, she replied, "Ten being dead? You're funny! Today is a good day... Yeah, today I choose life."

12.After Youn Yuh-jung won Best Supporting Actress at the 2021 Oscars, a reporter asked her a strange question about Minari executive producer Brad Pitt, who'd presented her with the award.

Here's the full clip, with this part starting at the 0:25 mark:

13.In 2018, the Jim & Sam Show asked Dylan McDermott for details about his mother's death.

Here's the full broadcast, with this part starting at the 31:50 mark:

14.When Cameron Diaz appeared on The Kyle and Jackie O Show in 2014, cohost Kyle Sandilands told her, "Let's hope [your onscreen daughter] misses out on the Drew Barrymore drug years, because those were a great thing to watch, but not so good to be in, I'd imagine."

Defending her best friend, Cameron replied, "I'm sure, Kyle, you've never been through a drug phase, have you? Or alcoholism or anything like that? Pretty clean…always did it right? Congratulations."

Then, invoking Cameron's husband, Kyle said, "Hang on a second, but I'm friends with Benji [Madden]."

Cameron replied, "We have to go now… Sorry, they're wrapping us up." Then the interview ended.

15.In 2017, Ellen DeGeneres turned the fact that English is Sofía Vergara's second language into an entire game.

Here's the full clip, with this part starting at the 2:14 mark:

16.And finally, Ariana Grande called out a sexist question during a 2016 radio interview with Power 106 FM.

You can watch the full video below, with this part starting at the 16:38 mark: