The businesswoman’s September 2007 appearance on The Late Show With David Letterman recently resurfaced online after The New York Times Presents’ “Framing Britney Spears” episode led social media users to reevaluate the way journalists treated female celebrities in the aughts.
During the interview, Letterman, now 73, repeatedly asked Hilton, now 40, about the three weeks she spent in jail that June for violating her probation by driving with a suspended license. He also badgered the socialite about her Simple Life costar Nicole Richie’s 82-minute stint behind bars that July for driving under the influence.
While Hilton called her time in jail “a really traumatic experience,” she was visibly uncomfortable and stayed relatively quiet on the CBS late-night show as the comedian continued to joke about her legal drama.
“Letterman’s team kept calling my PR team to have me be on the show, and we kept saying no. And then, months later, I had a fragrance coming out, and his team called again, and basically my PR team made an agreement with them that [jail] 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 recalled. “I felt like it was a safe place because I’d been going on Letterman for so many years, and he’d always have fun with me and joke around, but I thought he would keep his word on this, and I was wrong.”
Hilton reiterated that “there was not supposed to be one question” about her jail stint, but Letterman “just kept pushing me and pushing me” to talk about it.
“I was just getting so uncomfortable, and I was so upset,” she remembered. “It was like he was just purposely trying to humiliate me. And during commercial breaks, I would 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. Please don’t bring it up again.’ And he’s like, ‘OK.’ And then [he did] again.”
Looking back, the “Stars Are Blind” singer called the My Next Guest Needs No Introduction With David Letterman host “very cruel and very mean.” She explained to her podcast listeners that she felt Letterman had “crossed the line” and revealed that she told him she would never go on his show again.
“I didn’t tell him off because I’m not that type of person, but I got angry,” she said. “And then he was apologizing and, like, sent a case of Château Lafite Rothschild wine to our house.”
However, Hilton ultimately broke her own promise to herself, returning to Letterman’s set four times in 2008 and again in 2009, 2010, 2011 and 2013.
During her first time back, Letterman apologized on air, telling the House of Wax star that he “felt horrible” for pressing her and insisting that he was “not here to make enemies.” Hilton, for her part, responded with a laugh, “I hope you got the whole jail thing out of your system.”