Hilton recalls "crying and shaking" backstage after the interview and later recalls sitting through Sarah Silverman's "disgusting" set at the 2007 MTV Movie Awards.

By Joey Nolfi
March 02, 2021 at 11:19 AM EST

Paris Hilton has opened up about her traumatic relationship to the press throughout her early career.

As the pop cultural sphere continues to buzz about the media's treatment of celebrities in the wake of issues raised by FX's Framing Britney Spears documentary, the socialite and businesswoman took to her new podcast This Is Paris to revisit a turbulent period of her life in the public eye.

Inspired by what she calls Framing Britney Spears' "hard to watch" exploration of how journalists covered Spears' public struggles with mental health throughout the mid-2000s — including a now-controversial interview with Diane Sawyer — Paris and her sister, Nicky Hilton, recalled the former's 2007 appearance on CBS' Late Show With David Letterman, on which the acclaimed talk show host repeatedly asked the then-26-year-old about her three-week stint in jail for violating her probation in an alcohol-related driving incident.

"At this point I hadn't done an interview in months and months, because I didn't want to talk about it. Letterman's team kept calling my PR team to have me on the show, and we kept saying no," Paris revealed, adding that she eventually agreed to go on the show to promote a fragrance, but with one condition: "My PR team made an agreement to him that [the prison discussion] was off limits, and we would not discuss it, and we'd 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, and he'd always have fun with me and joke around, and I thought he'd keep his word on this. And I was wrong."

Paris explained that there was not "supposed to be one question" on the topic, but the host kept pushing her to the point where she was "so uncomfortable and so upset" to revisit her time in jail. In resurfaced footage from the interview, Paris tries to deflect Letterman's questions, telling him that she has "moved on" with her life and "doesn't really want to talk about it anymore," to which the audience applauded. But, Letterman pressed on.

"It was like he was purposely trying to humiliate me. During commercial breaks, I would look at him like, 'Please stop doing this, you promised me you wouldn't talk about this. That's the only reason I agreed to come on the show. Please don't bring it up again,'" Paris said, though there are no commercial breaks that appear in the eight-minute version of the segment currently on the internet. "It was just very cruel and very mean. After it ended, I looked at him and said, 'I'm never coming on this show again, you've crossed the line.'"

Paris said that she was "in tears, crying and shaking" as she left the stage, and immediately went to her sister, Nicky, who was waiting off-camera.

"I think it's fair game for him to ask you about it, but I think how he pushed it and pushed it.... he crossed the line," Nicky remembered. "Just to have a young girl up there and ask her questions designed to humiliate her is cruel. And I don't think that would happen today."

A representative for Letterman declined to comment on the 2007 interview for this article.

Still, Paris made a subsequent appearance on Letterman at the top of 2008, four months after the infamous interview. Letterman said he was "terribly sorry" for pressing her on the jail sentence, and later presented Paris with a bouquet of flowers as a peace offering.

But, on the podcast, Nicky insisted that her sister's troubled ties to the media didn't end with Letterman, and went on cite Sarah Silverman's set at the 2007 MTV Movie Awards — in which she made multiple jokes about Paris going to jail while the socialite sat in the audience — as causing further pain for the family.

"What Sarah Silverman did was so disgusting and so cruel and mean. I was so shocked and surprised because I'd actually met her a few years before when I was at an event and she couldn't be nicer. So sweet," Paris remembered. "I knew I was about to check myself into jail in a couple hours [so I was] trying to be brave. To sit in the audience with her just literally publicly humiliating me, being so mean, so cruel [about my prison time], I was sitting there wanting to die. I was trying to hold back my tears so hard. I had tears welling in my eyes, I wanted to run out of the entire room, but I just was trying to be strong and sit there, and the whole audience is laughing and she would not stop. It was so painful."

Representatives for Silverman didn't immediately return EW's request for comment.

Paris ultimately said the incidents were two of many in a long line of hardships that made her a stronger person.

"Now that I've really [experienced] life and realized so much about myself, I think the only reason I was able to go through all of that and be so strong is because I went through hell and back as a teenager," Paris finished, referencing her experience with abuse as a young girl. "Going through something like that made me very strong, almost like I was used to it. Which is sad to think, but I think if I hadn't gone through that, I don't know where I'd be at this point."

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