This is a preview of our pop culture newsletter The Daily Beast’s Obsessed, written by senior entertainment reporter Kevin Fallon. To receive the full newsletter in your inbox each week, sign up for it here.
Remember that quote. I’ll get back to it. I swear.
The reason for revisiting Letterman’s interview with Kardashian, which premiered on the streamer in October, is the recent spate of past Letterman interviews that have re-emerged and gone viral. They’re from when he was host of The Late Show. And they are all with female celebrities who, like Kardashian, were tabloid mainstays.
This happened after the recent Framing Britney Spears documentary detonated a sort of crisis of conscience about how cruel, unforgiving, violent, and, above all, misogynistic the media had been to Spears, and the ways in which we as consumers were complicit in fanning the flames.
In the documentary, people are aghast at the different lines of questioning Spears faced from journalists like Diane Sawyer or that European interviewer who asked the then-teen Spears about her breasts. It was a wake-up call to how we normalized invasive sexism and exploitation. It also was occasion to reconsider how other stars have been treated over the years, surfacing past examples of interviews that are similarly shocking when viewed through the hindsight of today.
And it happened that the interviewer who kept coming up was Letterman.
One of those examples was his 2007 interview with Paris Hilton, who spoke this week on her podcast about feeling humiliated by him. Her emotional realization came in the wake of watching Framing Britney Spears. At the time of the interview, Hilton was a comedy punching bag, having recently served time in prison. She says in the podcast that she was told Letterman would just ask one question about it. Instead it became the only thing he talked about.
“He just kept pushing me and pushing me and I was just getting so uncomfortable, and I was so upset,” she said. “It was just very cruel and very mean.”
A similar interview that went viral was with Lindsay Lohan from 2013, during which Letterman badgered the star about her rehab stint and sobriety despite the fact that she was visibly upset. Not only did she appear blindsided, but the sniveling tenor of the conversation fortified the stigma around addiction. The permission and entitlement he seemed to display reeked of misogyny.
Of course, that’s after viewing it through our 2021, #FreeBritney-branded woke glasses. Now more than then, when the interview actually played as funny, you can’t help but admire how well Lohan handled herself. She’s remarkable. But also, I worked in entertainment journalism at the time. I remember that this interview didn’t just escape criticism for being sexist. It was actually lauded.
Letterman’s interview skills were celebrated for getting her to “go there.” He got the scoop every media outlet was after: Lohan talking about rehab. It was a triumph, not a scandal. The same can be said about his interview with Hilton, which has often been exalted as one of the greatest late-night interviews of all time—a designation we’d cringe at now.
That is why it’s not exactly fair to place the blame on Letterman, who truly is one of the best celebrity interviewers and does have a knack for what’s become a lost art form in the increasingly PR-staged and vapid talk-show interview format. We were all entrenched in the deplorable mindset that this was OK, blinded to reality because we were all enjoying the amoral delusion.
It’s not just young starlets, by the way. I don’t know why this, of all late-night moments, sticks out to me, but I have a visceral memory of Letterman and bandleader Paul Shaffer orchestrating a bit when Julia Roberts appeared on the show in which they tried to get her to confirm a recent break-up. Shaffer, after some goading from Letterman, finally asked her, “You getting laid these days?”
But it’s because of this purported evolution and the hindsight we have now that I wanted to see what Letterman’s recent interview with Kardashian was like.
Viewing it through this angle, I was stunned that it starts with somewhat of a mea culpa. “Years and years ago I, and I think I was not alone about this, probably joked about you and your show,” he said. “Because I didn’t know. And that’s what I get paid to do, make jokes about that stuff. Everybody did. And here we are, and we’re not laughing now.”
It’s a fantastic interview. They talk about the fallacy of the idea of being famous for being famous. She talks about her relationship to O.J. Simpson and her experience during that case, her impression of the Trump administration after working with them, Caitlyn Jenner’s transition, the sex tape, and the robbery in Paris.
Letterman makes her feel comfortable and underlines every intimate question he has for her with dignity and validation. It’s probably why she’s so candid. It’s in stark contrast to the entrapment you see in the earlier Lohan and Hilton interviews. She’s not made to squirm like they were, where dishing the way he wants was the only way out of the discomfort.
Sure, his “creepy old man” character was still there. But it’s self-deprecating, not menacing. It’s why I was so struck by that opening quote that flashed on the screen: “My irritating personality is timeless.” Every moment of the Kardashian conversation feels like a Letterman interview. But it doesn’t feel like those Letterman interviews.
It’s a testament, to me, to how it’s not a stretch for the media to still function as the media—probing and interested in scandal—without reverting to lecherous and abusive old patterns. Yes, there are fundamental, systemic changes that have to be made. But small calibrations can be seismic, too.
Letterman is an interesting figure to be at the center of this post-Framing Britney Spears discourse about the media’s misogyny.
If today’s cancel-culture instinct is to scream “off with their head!” at the first whiff of something problematic, then Letterman has escaped the guillotine a few times. After a blackmail scandal, he confessed in 2009 to having sex with his female employees. He was accused of fostering a toxic workplace environment for female staffers, especially writers. And now these videos have resurfaced.
Of course, Letterman may be so venerated as to be non-cancelable, and his contrition has seemed genuine. It makes him and his legacy, which is still being dissected and considered, a test case for how things do or do not change over time. Is he a hero in this story just because he was nice to Kim Kardashian? No. But the uncomfortable interrogation he targeted at those starlets this time being aimed at him is, in some ways at least, progress.
One last thought on all this, kind of making the point that we were all in this then, and we’ve all tried to evolve our thinking since. On her podcast, Hilton also called out Sarah Silverman for making “vile, perverted” jokes at her expense around the same time as that Letterman interview, when Silverman hosted the 2007 MTV Movie Awards. They’re gross. “Imagine if that happened today?” she said about those jokes. “It wouldn’t.”
Here was Silverman’s response in her own podcast, which I’ll let speak for itself:
“She’s right. I would never do those jokes today. I’ve actually dedicated the past several years to trying to do comedy that marries hard-hitting jokes with, you know, actual heart. Back then, the consensus seemed to be that was not possible. And I fully accept that. I came up in a time when talk show hosts and comedians hired to make fun of pop culture were roasting the biggest celebrities and pop culture icons at the time. And nobody was bigger than Paris Hilton.
So here we are in an awakened world, and I’m totally into it. It’s how we grow. It’s how we change. I’m super down with reflecting on the past and my part in perpetuating real ugly shit. And yes, we can continue to litigate the past, but I do believe that maybe that should be coupled with taking into account any growth that has come with those passing years.”