With the Framing Britney Spears documentary casting a newly intense glare over the media’s treatment of women celebrities of the era, the footage of Hilton was one of multiple Letterman clips to resurface on social media this month.
The appearance came shortly after Hilton spent 23 days in prison for violating her parole – a subject which Letterman continued to press her on despite her repeated requests for him to stop asking her about what she called a “very traumatic experience”.
The majority of the segment comprised of Letterman asking her questions such as whether she ate alone in her cell, whether her friends treated her differently since she got out of “the slammer” and eventually saying: “This could be your legacy. This as a contribution to the young people of this country.”
“I’ve moved on with my life so I don’t really want to talk about it anymore,” Hilton said at one point, to which Letterman responded: “This is where you and I are different because this is all I want to talk about” – drawing huge laughs from his crowd.
Speaking on her This Is Paris podcast this week, Hilton described the interview as “cruel and very mean”, explaining that she had understood the subject to be “off-limits” ahead of her appearance on the show.
“I felt like it was a safe place because I’d been going on Letterman for so many years,” she said. “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 added. “Just being up there, it was like he was just purposefully trying to humiliate me.”
“And after it ended I looked at him and I said, ‘I’m never coming on the show again. You’ve crossed the line’,” Hilton said, claiming Letterman later sent a crate of wine to apologise.
When she appeared on his show the following year, Letterman said: “I found out afterwards I had offended you. I felt horrible about it because I’m not here to make enemies, honestly. So I called you, and you took the call, which I thought was very nice of you, and now you’re back and thank God, and I’m terribly sorry.”
In her podcast the previous week, Hilton said that the release of Framing Britney Spears had caused her to re-evaluate her relationship with the media during that period.
“I’ve been reading all of these articles coming out where they were just saying, like, Britney, Paris and a group of us were treated so unfairly and just like, this really misogynistic view and just being very cruel and mean and making fun of us,” Hilton said.
People reacted angrily to the resurfaced Letterman clip on social media, with some calling the interview “demeaning” and “sexist”.
indy100 has reached out to David Letterman for comment.