The reality star was left feeling ‘purposely humiliated’ after the host questioned her about her time in jail
In the viral clip, the host questions the reality star about her short stint in jail after she violated her probation following a drunk driving charge. “How’d you like being in jail?” Letterman asks, before the audience breaks out into laughter and applause. “That was just a horrible thing. Wasn’t that horrible?”
Letterman then asks Hilton to reflect on what she’s learned following her time in jail. “Obviously it was a very traumatic experience,” she responds, awkwardly shifting in her seat, “but I did it. I feel like I can do anything now.”
Now, speaking on her podcast, This is Paris, Hilton has described the encounter as “very cruel and very mean”. The socialite explained that she was on The David Letterman Show to promote her new perfume, and that questions about her jail time were agreed to be “off limits”.
“I felt like it was a safe place,” Hilton continued, “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. I was wrong. He kept pushing me and pushing me, and I was getting so uncomfortable and upset. It was like he was purposely trying to humiliate me.”
Hilton said that during commercial breaks, she would ask Letterman to stop probing her on the topic, but he never did. “He (was) getting people to laugh,” she recalled. “After it ended, I looked at him and I said, ‘I am never coming on this show again. You’ve crossed a line’.”
The reality star explained that Letterman apologised a number of times after the incident, even sending letters and gifts to her house. Hilton returned to the show in 2008, and at the start of the interview, Letterman apologised for “offending” her during their previous meeting.
“I forgave him,” Hilton said in her podcast. “(The next interview) was so much better, he knew not to do that again. I think he felt bad because a lot of people were getting angry that they saw it, even back then.”
A similar exchange between Letterman and Lindsay Lohan has also resurfaced on social media. During the interview, which took place in 2013, Letterman callously questions Lohan about her stints in rehab and her struggles with addiction.
Reflecting on the cruelty of the media at that time, Hilton stated: “I’m so happy that it’s different today. I wouldn’t wish what happened to me on anyone, not even my worst enemy. I’m really happy to see so many changes with the way people are talking about mental health now, the #MeToo movement, and just how women are finally respected. It’s a whole new world; it’s exciting that people are finally doing the right thing.”
Hilton also referenced the recent Framing Britney Spears documentary, which charts Spears’ rise to fame, the media’s obsession with her life, and her ongoing conservatorship. The reality star talked about the film in the previous episode of her podcast, stating that Spears is being “treated like a child”.
Now she’s watched the documentary, Hilton added: “I was heartbroken. It made me very emotional; I was crying a lot while watching it. Just from knowing her, she was such a sweet, down to earth, kind, gentle, amazing woman, and just to watch that whole story and see what the media did… it was very hard to watch. It made me very sad.”
Listen to the latest episode of This is Paris here.