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  2. Letterman, following up from events earlier in the program, asked Madonna to kiss a man in the audience; she refused. Letterman expressed admiration for her not succumbing to the pressure.

    • Madonna's Provocative First Appearance on David Letterman
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    When Madonna was married to her first husband Sean Penn, rumors floated around that she was having an affair with comedian, Sandra Bernhard. In reality, the two were just friends, but they had a lot of fun stirring the pot. Madonna would later tell Arsenio Hallthat she and Bernhard were friends because they both like to push people's buttons. By 19...

    In 1992, Madonna released her "Erotica" album and "Sex" book. The following year, her film Body of Evidencewas released. The sexuality of all three projects proved to be too much for the public, who heavily criticized Madonna as a result. The singer experienced a level of backlash that had fans worried about the future of her career. In 1994, Madon...

    Madonna and Letterman's first public appearance together since the infamous interview took place at the 1994 MTV Video Music Awards. The talk show host accompanied the singer on stage to present an award. During the moment, Letterman joked about her recent appearance on his show. "I'll be in the car," he said. "Watch your language." In 1995, Madonn...

    • Senior Author
  3. Mar 27, 2024 · Letterman started by jokingly encouraging her to kiss a fan in the audience. She wasted no time firing back “Why are you so concerned with my sex life?”. A minute in, she turned to Letterman and said “Incidentally, you are a sick fuck.”

  4. Oct 1, 2021 · Her guest appearance started out innocent enough, with Letterman welcoming Madonna on stage, but it soon turned awkward — even for the viewers in the studio. As Far Out Magazine recounted, Letterman goaded the singer to kiss a guy in the audience, which Madonna refused, saying that she didn't succumb to pressure and calling the host a "sick f ...

    • Jean Mendoza
  5. Aug 7, 2024 · At the start of the interview, Letterman, then aged 47, told Madonna to kiss a guy in the audience on the forehead as it would ‘knock him out.’

  6. Mar 31, 2024 · Madonna claimed that Letterman had gone soft since becoming successful, insisting “you just kiss up to everybody on your show now.” Letterman cheekily offered to “suspend that behavior tonight”...

  7. Mar 31, 2021 · 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.