Speaking on The Sarah Silverman Podcast, the 50-year-old said she was out of line when she publicly mocked Hilton at the 2007 MTV Movie Awards, while the star was sat in the front row.
At the time, Hilton was to immediately report to jail after the ceremony to do time for violating her probation in an alcohol-related reckless driving case. She ended up serving just three days of her 45-day sentence.
“I heard to make her feel more comfortable in prison the guards are going to paint the bars to look like penises. I am just afraid she is going to break her teeth on those things,” the comedian, who was hosting the show, told the crowd as Hilton awkwardly attempted to laugh off the joke.
But as Silverman reflected on her stand-up gig that night, she recalled seeing Hilton looking visibly upset and she immediately regretted her “ugly” comments.
“The crowd went bananas, and while I was thrilled at the success of my monologue, I remember spotting her in the audience, I really do, and I remember seeing that look on her face and my heart sank,” Silverman said on her March 4 podcast.
“There was a person under there. A couple days later I wrote her a letter apologising, felt awful and I never heard back, I certainly wouldn’t expect to, anyways.
“I regretted the jokes not years later, but kind of immediately. I wrote to let her know, but I know now that the letter didn’t get to her. So, here I am, 14 years later, telling you, Paris, that I am really sorry.
“I was then and I am, much more completely and with far more understanding, I think, now … It feels terrible to know you have hurt someone and it’s important to make it right. So, I hope this does that.”
Silverman’s apology comes days after Hilton, now 40, revealed on her own podcast, This Is Paris, that she had to hold back tears after hearing the joke.
“I was obviously very nervous and knew I was about to check into a jail a few hours later, I put on a brave face and she literally pummelled me, so mean, so cruel,” Hilton told her sister Nicky Hilton during the March 2 episode.
“I was sitting there, wanting to die, I was holding back tears, I had tears in my eyes… I literally wanted to run out of the entire room. The whole audience was laughing and she would not stop. It was so painful especially with what I was going through in my life, it was really hard.”
Nicky told her sister Silverman’s remarks were “vile” and completely unnecessary.
“Mum always told us you don’t know someone until you have walked a mile in their shoes and here Sarah was … saying the most disgusting vile, awful, hurtful things,” Nicky said.
“I understand she is a comedienne and she is there to be funny and make people laugh, but when you have to put people down and insult people to get a laugh, it’s not funny. I didn’t think it was funny then and I certainly don’t think it is funny now.”
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