Madonna's Most Memorable 'Letterman' Appearances

oct 01, 2009 : Madge's visit on Wednesday night marked her eighth appearance on the show.

Wednesday night marked the eighth time Madonna has appeared on David Letterman's show, and as expected, each visit has been memorable for one reason or another — Madonna herself said to Letterman on Wednesday night, "Every time I'm on the show I feel like I'm a different person. I'm not myself. I think I may have made a fool myself once or twice on your show as well." With that in mind, we took a look back at her most memorable — and controversial — sit-downs with the talk-show host.

In 1988, Madonna made her first appearance on "Letterman," alongside then-sidekick/ now-former friend Sandra Bernhard — the two appeared in matching outfits (denim shorts and white T-shirts), and flirted with him fairly outrageously. Madonna and Bernhard described a typical night out together, and Dave asked if he could "be a part of it." Madonna later said of Bernhard, "We do odd things and we split each other's split ends." To conclude the appearance they jokingly tussled and kept talking about "getting real," implying that they were having a romantic relationship. When Dave wanted to cut to commercial break, they flailed their arms around, aggravated that their appearance had to come to a close.

In probably her most controversial appearance on the show, in 1994 Madge dropped a stunning number of four-letter and clutched a pair of her own underwear — she even went as far as to ask Letterman to smell them a few times. She freely talked about her sex life and claimed she was angry with Letterman for doing the same. She asked Letterman whether he had ever smoked "endo" (slang for marijuana); Dave reacted as if he had no clue what she meant. She then refused to leave the stage before finally doing so three commercial breaks later.

Perhaps in an effort to mend fences after the 1994 appearance, Madonna made a brief appearance on Valentine's Day the following year, presenting Letterman with flowers and claiming, "I am a changed man since I met you... I no longer say the word 'f---' anymore."

In 2000, Madonna sat down with Letterman and discussed the 1994 appearance. She claimed to have been in a "rebellious period" in her life that she was now far past. Letterman sympathized by stating how "beat up" she must have felt during that era due to all the negative press she had been receiving at the time (much of it stemming from her controversial "Sex" book).

Dave remarked "I still have the panties. We had to put them in the vault upstairs, because people were trying to swipe them from me." Appearing shaken by the comment, Madonna said, "I won't rise to that bait."

Madonna showed she'd changed even more during her visit to the show in 2005, where she and Dave talked about parenting. She also talked her horseback-riding accident, which resulted in a few broken bones earlier that year. Dave and Madonna then hit the streets of NYC — on horseback. Madonna said, "I have a bit of excitement tainted with fear," before climbing on — and who could forget the sight of Madonna and Dave riding off into the sunset on horses? - Courtesy By MTV.com


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