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Resurfaced interview shows David Letterman creepily asking Janet Jackson about her wardrobe mishap

A resurfaced 2004 interview shows David Letterman pressing Janet Jackson about her Super Bowl incident despite her discomfort

An old interview from 2004 between David Letterman and Janet Jackson has resurfaced, and people online are calling it out. This comes after another one of Letterman’s interviews, with Lindsay Lohan in 2013, went viral for being uncomfortable to watch. One social media user, @ryancortezz, shared the Janet Jackson clip on X, comparing it to the Lohan interview. “This gives off the same vibe. I don’t know how he gets away with it," the video was captioned. 

At the start of the interview, Letterman greets Jackson and immediately makes a remark about her outfit, saying, “Now that’s almost malfunctioning, isn’t it?” Jackson smiles awkwardly but doesn’t respond. He then brings up her Super Bowl performance and asks, “Let’s run through this. Tell us exactly what happened from the time you got up on Super Bowl Sunday to the time the episode took place on the halftime show.” As the audience laughs, Jackson shakes her head and replies, “I don’t want to relive any of that.” Letterman continues, asking, “You don’t mind if I ask you some questions about it, though? First of all, you knew it was going to happen, right?” Clearly frustrated, Jackson pleads, “Oh, god can we talk about something else, please? I’ve had a day of interviews. I’m sure you guys are sick of hearing about it, I know I am.” She then turns to the audience and asks, “Ask me about something else,” as per Newsweek.

Despite this, Letterman doesn’t stop and keeps questioning her for a few more minutes before making his point. “[Timberlake] grabs at a woman, you, and he pulls her thing off. That sends a very bad message to young boys in this country, that you go up to a woman, even under the guise of a show business production, and pull her thing off. You’re not supposed to behave that way.” Jackson, confused, asks, “Pull her thing off?” He then says, “That’s what happened, he pulled your thing off, didn’t he?” She asks, “My thing off?” “Well, what did he pull off,” he asked. “It seemed like a piece of clothing to me. It wasn’t my ‘thing.’ He didn’t touch my ‘thing,’” replied Jackson.

Letterman continues, “It sends a bad message don’t you think?” She then asks, “Why are we talking about this right now, David?” He then brings up the fact that he has become a father since he last saw Jackson and claims her performance sent a bad message. “I would not want him to see somebody, a young woman, to see somebody rip a piece of her clothing.” Jackson responds, “To see a breast?” Letterman awkwardly admits, “I ain’t got no problems under the right circumstances, you know. And by the way, he sees plenty. He’s getting a lot more than Daddy.” Finally, Jackson firmly says, “Can we talk about something else? Because I don’t want to focus on my breasts.”

David Letterman has faced criticism for his harsh questions to Lindsay Lohan on his show about her substance abuse. During the 2013 episode, Letterman asked her, "Aren’t you supposed to be in rehab? What are they rehab-ing? What is on their list? What are they going to work on when you walk through the door?" He also added, "Do you have addiction problems? Is it alcohol? Do you drink too much?" While the audience laughed, Lohan answered the questions but noted they were not discussed beforehand. She later told Letterman not to "make a joke of it" because it is "mean." Deadline reported.