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The infamous moment Madonna appeared on Letterman


Before Madonna became British, she made an iconic potty-mouthed appearance on The Late Show with David Letterman, an infamous occasion that took place on this day in 1994. 

The superstar wanders onto the set looking like the love child of a Hollywood golden era actress and a New York CBGB’s punk and greeted David by calling him “the man who has his finger on the pulse of total strangers”. Letterman, responding, said: “I’m only here because there isn’t a Knicks game, let’s not get excited.”

The pair then proceeded to talk about Madonna’s apparent love of basketball, but it quickly ran aground and ventured into the murky territory of ball games of a different kind. The diatribe of swearing and innuendo that followed was, in fairness, prompted by a pretty rogue and inappropriate comment from Letterman whereby he yelled, “Go kiss a guy in the audience!” stating that it would make his day. 

It quickly became clear that the pair had previous, and that ‘previous’ in question quickly revealed itself as it would seem that, before the show, Madonna had ‘gifted’ Letterman a pair of dirty panties and continually implored to know why he hadn’t sniffed them yet. This utterly bizarre, and frankly unsettling, revelation followed what seemed like an inexplicable declaration from Madonna as she casually turned to Letterman, saying, “Incidentally, you are a sick fuck.”

What followed was an interview that careened around an assault course of swearing, sexual innuendo and some sort of strange tension, as Letterman and producers frantically tried to regain some control over the runaway show. 

Every time Letterman tries to wrestle the conversation back into a safer live TV terrain, it pings back towards like platitudes in an instant. He drags the chat back onto NBA and Madonna’s eyes wander up to the ceiling mic where she proclaims: “That microphone is really long… speaking of the NBA.”

It later becomes clear where Madonna’s antics are rooted. In the run-up to the show, Letterman had made a series of gags relating to the singers ‘liberated sex life’, and his segment of bits had not gone unnoticed. “You can’t get through a show without talking about me,” she announces, before adding: “Or at least thinking about me.” She quickly follows by saying, “You are always fucking with me… on the show,” a gag that is repeated more times than Home Alone at Christmas time. 

Once the swearing and comedic tension finally wears thin, Letterman gets as close to issuing a chastening as the witty host ever comes, as he tells her, “People don’t want that [swearing] in their own homes at 11:30 at night.”

He then cuts to a commercial for what seems like the hundredth time that night and the concluding couplet of the interview is Madonna protesting, “Can’t this go on and on?” and Letterman shooting back, “It feels like it already has.”

The retrospective conclusion, however, is that this is perhaps the most early-nineties TV moment in history. There is so much to be judiciously analysed in the clip, in terms of societal dynamics and changing times, that the twenty-minute interview could make a decent sociology university thesis, or at the very least an incisive Bob Dylan song.