Janet Jackson looked uneasy when Letterman brought up one disturbing topic: "You don't mind if I..."
David Letterman's interview with Janet Jackson was all things awkward! In 2004, Jackson appeared on an episode of 'Late Show with David Letterman,' and during the episode, the late-night talk show host asked Jackson about her infamous Super Bowl performance. According to a report by Entertainment Weekly, when Jackson stepped on the stage, Letterman gave her a warm introduction by saying, “Welcome to the show." Soon after, Letterman remarked on her revealing outfit by saying, “Now that’s almost malfunctioning, isn’t it?” Then, Jackson adjusted her attire. For her stint on Letterman's show, Jackson dolled up in a cleavage-baring, two-piece red gown.
Later in the episode, Letterman asked Jackson, “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 crowd broke into laughter, Jackson shook her head and laughed awkwardly and went on to say, “I don’t want to relive any of that.” As per Scary Mommy, Letterman questioned Jackson, "You don’t mind if I ask you some questions about it, though? First of all, you knew it was going to happen, right?” Then Jackson, who appeared visibly uncomfortable, said, "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." Shortly afterward, Jackson looked towards the studio audience and asked them to help her out of the situation. “Ask me about something else," Jackson stated.
Letterman didn't let go of the topic so easily and said, “[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." In her response, Jackson said, “Pull her thing off?” Meanwhile, Letterman uttered, “That’s what happened; he pulled your thing off, didn’t he?” A confused Jackson asked, “Is my thing off?” to which Letterman retorted, “Well, what did he pull off? It seemed like a piece of clothing to me." Following that, Jackson remarked, "It wasn’t my ‘thing.’ He didn’t touch my ‘thing.’”
Then, Letterman stated, “It sends a bad message, don’t you think?” to which Jackson replied, “Why are we talking about this right now, David?” In the same interview, Letterman mentioned he had become a father since the last time he saw Jackson and specified that he didn't like the message her Super Bowl Halftime sent to the viewers. Letterman said, "I would not want him to see somebody—a young woman—to see somebody rip a piece of her clothing," to which Jackson replied, "To see a breast?” Soon after, Letterman noted, “I don’t have any problems under the right circumstances, you know. And by the way, he sees plenty. He’s getting a lot more than Daddy.” On the other hand, Jackson requested Letterman to change the topic by saying, “Can we talk about something else? Because I don’t want to focus on my breasts.”
For the unversed, let us tell you that Jackson performed with Justin Timberlake at the Super Bowl XXXVIII halftime show, and during the performance, Timberlake pulled off part of Jackson’s outfit, which exposed her right breast in front of the television audience. Up until now, Jackson's wardrobe malfunction continues to be one of the most controversial moments in the history of the NFL's annual event.