"It was like he was purposely trying to humiliate me."
Paris Hilton revisited a pair of uncomfortable public appearances from the time around her 2007 jail sentence: Sarah Silverman roasting her at the MTV Movie Awards the night before she checked in and David Letterman grilling her about her time behind bars when she got out.
Both topics came up on the latest episode of Hilton's "This Is Paris" podcast, which featured an appearance from her sister, Nicky Hilton. After Nicky mentioned that she had just watched the "Framing Britney Spears" documentary, cohost Hunter March said the doc led to a lot of old interviews with young, female stars getting looked at in a new light -- including Hilton's Letterman appearance.
In 2007, Hilton was sentenced for 45 days behind bars for violating her DUI probation by driving on a suspended license. After three days, she was placed on house arrest, before being hauled back to jail. In the end, she served 22 days.
During the 2007 appearance, Letterman kept asking Hilton about her recent jail stint -- even after she said she didn't want to talk about it anymore. She appears uncomfortable with the line of questioning and even tells him, at one point, "You're making me sad that I came. You're hurting my feelings."
Talking to her sister about the interview, she claimed her PR team told his people that jail questions were "off limits" and she would only be on to talk about her latest perfume and other business ventures. "I felt it was a safe place because I had been going on Letterman for so many years. I thought he would keep his word on this and he was wrong," she explained. "There was not supposed to be one question and he kept pushing me and pushing me. I was just getting so uncomfortable and upset."
"Nicky, you were backstage, I remember talking to you after and being up there, it was like he was 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," she claimed. "He was like okay and then again [brought it up]. It was very cruel and very mean. After it ended I looked at him and said I am never coming on this show again, that crossed the line. I didn't tell him off because I'm not that type of person, but I got angry and he was apologizing and sent a case of Chateau Lafite Rothschild wine to our house."
She added that she was "in tears, crying and shaking" after the appearance, but eventually forgave him after he "kept apologizing" and allegedly sent letters and made numerous calls to her team. "Finally, I said okay I'll come back on your show. I said okay and I forgave him," she added, saying the follow-up appearance was "so much better."
"He knew not to do that again," she added. "I think he felt bad, I heard a lot of people were getting angry they saw that, even back then. I'm so happy that it's different today."
When she appeared on his show again in 2008, he apologized profusely and presented her with flowers. After saying people told him he acted like an "ass" in the previous interview, he added, "I offended you. I’m not here to make enemies, honestly. I'm terribly sorry."
A rep for Letterman told TooFab they had nothing to add aside from that 2008 apology.
While Nicky said she thought it was "fair game" for him to ask about her prison sentence, she didn't appreciate how he kept pushing. She then said that Paris went through a lot that wouldn't happen today, bringing up Sarah Silverman's jokes at her expense at the 2007 MTV Movie Awards.
"You know what would not happen today? Is Sarah Silverman going on stage at the MTV Awards and making disgusting, vile, perverted statements about pop stars, people sitting in the audience," she said.
During her opening monologue, Silverman took aim at Hilton. "Paris Hilton is going to jail," she exclaimed, getting a huge applause from the audience. "I heard that to make her feel comfortable in prison, the guards are going to paint the bars to look like penises. I just worry that she's gonna break her teeth on those things."
"What Sarah Silverman did was so disgusting and so cruel and mean," said Hilton, looking back now. "I was so shocked and surprised because I'd actually met her a few years before when I was at an event, she couldn't be nicer, so sweet. I was obviously very nervous, I went to the MTV Awards, I knew I was about to check myself into jail in a couple hours ... trying to be brave and then to sit in the audience with her literally publicly humiliating me, being so mean, so cruel, I was sitting there wanting to die."
"I was trying to hold back my tears so hard. I had tears welling up in my eyes, I literally wanted to run out of the entire room," she continued. "Would not stop. It was so painful, to then have someone be so mean about it was really hard."
Silverman has since expressed regret over her comments, especially after seeing the reaction to her joke.
"I had no moral qualms, in theory, with joking about Paris' incarceration -- it's what late-night talk-show hosts had been doing for weeks," she wrote in her book "The Bedwetter: Stories of Courage, Redemption, and Pee." "But to set her up to be jeered to her face by thousands on live television during the most vulnerable, frightening moment of her life -- needless to say, that took the fun out of the 'all in good fun' essence I intended."
She added that she felt "horribly guilty" at the time and even wrote a letter to Paris, who was, by that point, behind bars. During her podcast, however, Hilton said she's never talked to Silverman since that show.
TooFab has reached out to Silverman's rep for comment.
Paris went on to say that she was able to get through even the most humiliating moments like these because she had already gone through "hell" as a teenager, referring to the alleged abuse she suffered as a teenager at a private boarding school.
"I think going through something like that, it made me very strong and almost like I was used to it," she added. "Which is sad to think. I think if I hadn't went through that, I don't know where I'd be."