Celebrity Paris Hilton Paris Hilton Recalled a "Cruel" and "Humiliating" Interview with David Letterman The TV host repeatedly grilled her about her 2007 jail stint. By Tessa Petak Tessa Petak Instagram Tessa Petak is a Brooklyn-based writer who helps to cultivate InStyle's illustrious news coverage across a wide range of topics including celebrity, fashion, and entertainment. She also produces and composes celebrity profiles and features for the site and InStyle's digital issues. InStyle's editorial guidelines Published on March 2, 2021 @ 08:40AM Pin Share Tweet Email The Framing Britney Spears documentary has prompted a more widespread conversation about past unfair treatment that young celebrities experienced from the media. Now, Paris Hilton is recalling a traumatic interview with David Letterman. On her new podcast This Is Paris, the hotel heiress spoke with her sister Nicky Hilton about the "cruel" and "humiliating" interview. In the 2007 interview, Letterman continuously grilled Paris about her 3-week period in jail, a topic her team had made clear was "off limits" prior to her appearance on the show. In fact, she refused his invitation to come on the show for months because she did not want to speak about this traumatic moment in her life. But eventually she agreed to come on the show to promote her fragrance, on the condition that he would not bring up her jail stint. "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 on her podcast. "I felt like it was a safe place because I'd been going on Letterman for so many years." She added, "He'd always have fun with me and joke around, but I thought he would keep his word on this and I was wrong." A Resurfaced Jennifer Aniston Interview Has Fans Disgusted With David Letterman During the interview, Letterman asked, "How'd you like being in jail?" Paris recalled him continuously pushing for her to answer. "I was just getting so uncomfortable and I was so upset," she remembered. "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 continued, saying that he would agree to stop making jokes during the commercial breaks, but as soon as the cameras started rolling, he'd use it as an opportunity to make the audience laugh. "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.'" Other controversial David Letterman interviews have recently surfaced, including one where the TV host makes suggestive remarks to Jennifer Aniston before sucking on a strand of her hair. Another shows him pressing Lindsay Lohan to speak about rehab.