More than a decade after it aired, Hilton opened up about how much the interview hurt.

Olivia Harvey
Updated Mar 03, 2021 @ 1:17 pm
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Update, March 3rd, 2021: After Paris Hilton's 2007 interview with David Letterman was resurfaced by the internet, the star herself responded to how inappropriate it all was. Hilton spoke to E! News on March 1st about her visit with Letterman, calling it "so uncomfortable."

Hilton was originally scheduled to appear on the show to promote her fragrance, and she told E! News that her criminal record had been taken off the table as far as conversation topics would go on the show. "That was off limits and 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."

However, Hilton was blindsided by questions about jail, which she was visibly uncomfortable with. "Just being up there, it was like he was purposefully trying to humiliate me. And during commercial breaks I'd look at him, like please stop doing this. You promised me you wouldn't talk about this and that's the only reason I agreed to come on the show." She also added that during commercial breaks, he'd tell her that he'd stop, but as soon as the cameras started rolling again, he'd go back in on her—trying to get a laugh from the audience at her expense.

"It was just very cruel and very mean," she said. "And after it ended I looked at him and I said I'm never coming on the show again. You've crossed the line." Over the years, though, Hilton said Letterman profusely apologized and she forgave him, and we can only hope he apologized to the other stars he purposely hurt on the show, all for the sake of shock value.

Original story, February 17th, 2021: In the wake of The New York Times Presents: Framing Britney Spears, early-2000s celebrity culture is being looked at again under a modern microscope. The Times documentary, available to stream on Hulu, showed viewers how tabloid press and paparazzi ultimately caused Britney Spears' mental health decline and eventual break, which she's still feeling the effects of a decade later. But Spears wasn't the only target—friend Paris Hilton was also dragged in the tabloids, and an interview from 2007 is currently causing outrage on Twitter.

Hilton stopped by The Late Show With David Letterman in 2007 to promote her new film and perfume, however, for comedy's sake, Letterman took the conversation in a much different direction. About 15 seconds into the interview, Letterman asked her, "How'd you like being in jail?"

Earlier that year, Hilton was sentenced to 45 days in jail after violating probation for a previous reckless driving offense. Letterman's questions about her serving jail time were met with raucous laughter and applause while Hilton had no choice but to literally grin and bear it.

"I've moved on with my life so I don't really want to talk about it anymore," she said, but her request fell on deaf ears. "This is all I want to talk about," Letterman responds. And he does. He asked her if she drinks and drives, if she made friends in jail, if she sees herself as a role model for kids who may be going down a similar path.

The interview goes on for eight minutes, and about six of those minutes are jail talk. When Hilton finally does manage to move the interview forward, her career moves are met with laughter because no one in the audience could take her seriously after such a takedown.

Hilton's interview with Letterman resurfaced after a 2013 Letterman interview with Lindsay Lohan lit up Twitter on February 13th. "Aren't you supposed to be in rehab now?" Letterman asked Lohan, who had been struggling with addiction at the time.

Luckily, Lohan literally takes control of the interview by taking Letterman's notes and calling him out for being "so mean" and telling him "we're not doing that" when he wanted to list negative things Lohan had recently "endured."

Both interviews have since been called misogynistic, blindsiding, bullying, and judgmental by 2021 audiences. And the fact that both Lohan and Hilton note that these prying, personal questions were not brought up in the pre-interview shows how ethics were stomped on in order to get a laugh and point the finger at the "hot mess" of the moment.

Of course, it wasn't just David Letterman who pulled these punches. As Framing Britney Spears explained, tabloids that wanted to sell magazines painted their own dramatic picture of what was happening in personal lives of famous young women. Because social media had not gained traction yet, it was nearly impossible for Spears, Hilton, Lohan, and others like Amanda Bynes and Miley Cyrus to shape their own narrative.

These women were mocked by media and the general public for being famous, and even when they were given a chance to go on television and tell their story, there was no way for them to escape the criticism.

The early- and mid-2000s were a dangerous time to be young, female, and famous. It may have taken the public more than 10 years to see how cruelly these women were treated, but we finally woke up and realized that laughing at young women trying to find themselves and maintain their mental health amidst the spotlight is, and never was, okay.