Madonna's awkward chat with David Letterman remains cringeworthy even after 30 years.

The show made history on TV.

August 7th 2024.

Madonna's awkward chat with David Letterman remains cringeworthy even after 30 years.
Back in 1994, Madonna's interview with David Letterman was the talk of the town. Even now, after three decades have passed, the memories of that sit-down conversation still make us cringe with awkwardness. It was truly a historic moment in TV history, as Madonna managed to drop the f-bomb a whopping fourteen times, making it the most censored US network talk show ever.

During the interview, the then 34-year-old singer shocked audiences by chugging on a cigar, throwing insults left and right, and even producing a pair of her own knickers. Needless to say, her behavior outraged viewers, who flooded the Federal Communications Commission with complaints. Critics also had a field day, with The New Paper stating that Madonna had hit rock bottom with her antics on the show.

But let's take a closer look at all the controversial moments from that fateful March 31, 1994 episode of Late Show with David Letterman, featuring the one and only Madonna.

At the start of the interview, the 47-year-old Letterman had a rather unusual request for Madonna: to kiss a random audience member on the forehead. However, the singer politely declined, stating, "I can't." Letterman then commended her for not giving in to peer pressure.

But that was just the beginning of Madonna's wild behavior. She went on to ask Letterman to smell her underwear, which she had apparently brought for him as a gift. When he seemed taken aback, she insisted, "Wait a minute, aren't you going to smell them? I brought them for a reason." Letterman, at a loss for words, simply sighed and appeared to throw the underwear off-camera.

The tension between the two only escalated as the interview went on. Madonna seemed determined to keep Letterman on the edge, as she refused to cut to commercial breaks, stating, "I don't think we should ever cut to a commercial. Let's just keep taping every second of it." Of course, they eventually had to give in to contractual obligations, but even then, Madonna tried to shut down the second break.

But perhaps the most bizarre moment of the interview came when Madonna started talking about peeing in the shower, claiming it had health benefits. The audience was left awkwardly laughing, unsure of how to react.

There were also some uncomfortable innuendos, with Madonna commenting on Letterman's long microphone and then saying, "Speaking of the NBA..." before adding, "I'm sorry, I always go there." And when Letterman asked her about her nose ring, she responded with a joke about something else hurting.

The two also traded insults, with Madonna asking if Letterman's hair was a "rug" and him responding by describing her hair as a "swimming cap." Madonna even commented on Letterman's relationship status, seeming surprised when he said he had a girlfriend.

But perhaps the most surprising moment of the interview was when it ended and Madonna refused to leave. She told the audience she would "still be here" and wasn't "going anywhere." A producer had to intervene and "get rid" of her so that the next guest, Counting Crows, could make their network TV debut.

Despite the chaos and discomfort of that interview, Madonna and Letterman were able to put it behind them. In fact, Madonna even made a brief appearance on the Late Show the following year, bringing Letterman candy and declaring that she was a "changed woman." And in 2000, she returned for her first full-length interview since the notorious 1994 episode, where they both addressed the awkwardness and Madonna chalked it up to her "rebellious period."

Madonna has since made several more appearances on the Late Show, and in 2015, she even reflected on the 1994 episode during an interview with Howard Stern, stating that she was in a "weird mood" that day due to her relationship with Tupac Shakur. Despite the controversy, it seems that both Madonna and Letterman have moved on from that infamous interview.

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