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Paris Hilton Opened Up About Her "Cruel" And "Purposefully" Humiliating 2007 Interview With David Letterman After An Extremely Awkward Clip Resurfaced

"I was just getting so uncomfortable and I was so upset. During the commercial breaks I'd look at him like, 'Please stop doing this.'"

Posted on March 2, 2021, at 10:15 a.m. ET

Ever since the release of Framing Britney Spears earlier this year, fans have been looking back at the way famous women were treated by the media in the early 2000s.

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Many people have revisited old interviews, pointing out how inappropriately women celebrities were questioned and treated by certain men in the media. And one person who has come up repeatedly is David Letterman.

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Letterman was initially criticized after this 2013 interview with Lindsay Lohan resurfaced, where he repeatedly probed her about her arrest for shoplifting and recent spell in rehab.

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"Aren't you supposed to be in rehab right now?" Letterman asked at one point in the interview. "What are you rehabbing? Do you have addiction problems? Is it alcohol? Do you drink too much?"

But soon many others came to light, including him failing to respect the boundaries of everyone from Janet Jackson to Jennifer Aniston and Beyoncé.

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And now another extremely uncomfortable interview from 2007 has resurfaced, this time involving Paris Hilton.

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Hilton was ostensibly on the show to discuss her new perfume, but after Letterman asked her whether she preferred spending time in LA or New York, he then fired this question at her: "How did you like being in jail?"

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For those who don't know, Hilton was sentenced to 45 days in jail in 2007 after an alcohol-related reckless driving charge. In a documentary released last year, Hilton revealed that the experience was deeply traumatic after attending Provo Canyon School during her childhood, where she claims she was forced to spend time in isolation.

"That was a horrible thing," Letterman said in reference to her time in jail. "They locked up your friend Nicole [Richie] — she was only in for a short period of time wasn't she? She was only locked up for 45 minutes. Tell me, how does that work? How can somebody only be in for 45 minutes?"

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"I don't know," Hilton awkwardly responded.

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"Looking back on that experience, what can you tell us? What have you learned? What's different about you?" he went on to fire at her.

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A visibly uncomfortable Hilton replied: "Obviously it was a very traumatic experience, but I survived it, so now I can do anything."

Letterman continued to bombard Hilton with questions about the food in jail despite her only offering monosyllabic responses.

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"I suppose the food was awful," he said. "Did you have three meals a day? Did you start with breakfast? What would that be? Lunch? How were the bologna sandwiches? Is there a midafternoon snack? Do you go right to dinner? Are you eating alone in your cell or was it a common dining area? What was dinner usually? Of the three meals, I guess the only thing you wanted to eat was the breakfast, right?"

"Did you lose a lot of weight while you were in prison? What did you do to keep your energy up?" he continued.

He then pontificated about how "bizarre" her jail sentence had been, questioned why she was arrested, asked if she "still used alcohol," and probed as to whether her friends treated her differently now she was "out of the slammer."

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And when Hilton said she didn't want to talk about the subject anymore, Letterman made it clear he still did. He sarcastically asked if she'd received any letters from "kids and teachers and clergymen" describing her as a role model, before saying "this could be your legacy."

At this point, Hilton became silent and slightly tearful. When an audience member shouted: "I love you, Paris," Letterman asked: "Is that somebody you met in prison?"

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Hilton was left with just one minute to discuss the projects she'd actually been invited onto the show to promote, while the audience audibly laughed and mocked her.

Well, Hilton has now spoken out about the "cruel" and "mean" interview, accusing Letterman of "purposefully trying to humiliate" her.

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Speaking to E! News, Hilton revealed that Letterman had actually agreed ahead of time that the subject of jail would be off-limits, and that's the only reason she'd agreed to the interview in the first place.

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"That was off-limits, and [we agreed] he would not discuss it and we would only be there to promote the perfume and my other business ventures," she said. "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."

"I was just getting so uncomfortable and I was so upset," she went on. "Just being up there, it was like he was purposefully trying to humiliate me."

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"During commercial breaks I'd look at him like, 'Please stop doing this,'" she added. "'You promised me you wouldn't talk about this and that's the only reason I agreed to come on the show.'"

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She went on to say that while he kept promising to stop the jokes, he began again as soon as the cameras started rolling.

"It was just very cruel and very mean," she concluded. "And after it ended I looked at him and I said, 'I'm never coming on the show again. You've crossed the line.'"

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And while Hilton eventually made amends with Letterman and appeared on his show numerous times after he "continually apologized" for his actions, she believes herself and other pop stars were "targeted" by the media in the 2000s.

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"I would see that with myself, with Britney [Spears], Jessica Simpson. There was a certain type of girl they targeted that they'd never do that to a man," she said.

You can read the full interview with Paris Hilton here.

A BuzzFeed News investigation, in partnership with the International Consortium of Investigative Journalists, based on thousands of documents the government didn't want you to see.

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