Madonna made an appearance on Late Show with David Letterman on March 31, 1994.

In a subsequent interview with USA Today, Letterman noted how Madonna sent him a fax on his birthday, shortly after the episode aired. For example, in an episode of The Critic titled "Sherman, Woman and Child", Madonna is featured as a profane guest of Humphrey the Hippo, a parody of Barney & Friends.

In the Space Ghost Coast to Coast episode "Bobcat," comedian Bobcat Goldthwait sarcastically comments to the character Moltar that Space Ghost's interview with The Ramones "is going as well as the Letterman-Madonna interview." Following the incident, Madonna's appearances on Letterman did not end.

The Federal Communications Commission received numerous complaints about the language used on the show, echoing Letterman's (sarcastic) remark that she had to stop using the bad language "because people don't want that in their own homes at at night".

This was not Madonna's first or last appearance with Letterman.

The home audience never saw Madonna leave her chair; instead, the show cut to a third commercial break, after which the singer was gone.

Letterman said, "Coming up in the next half hour, Mother Teresa is going to drop by." He then looked at an index card and joked, "Oh, I see we've been canceled, there is no show tomorrow night." Another guest, who was the United States Grocery Bagging Champion at the time, was scheduled to appear on the show that evening, but his segment was cut, due to Madonna refusing to leave the stage when her interview was over."), Madonna laughed and said "I thought you were going to ask me if it hurt something else..." which spurred a collective series of nervous laughter from the studio audience.Prior to the first commercial break (which Madonna objected to, citing that she wanted to "break the rules" and not conform to the constraints of American network television), the star asked Letterman if he was wearing a "rug"; never missing the opportunity for a joke, the host, referring to Madonna's short slicked-down hairstyle, replied by asking Madonna if she was wearing a swim cap.In particular, Madonna said the word "fuck" fourteen times during the course of the interview.This made the episode the most censored in American network television talk-show history while at the same time garnering Letterman some of the best ratings he ever received.She was a guest on Late Night with David Letterman in 1988 with comedian Sandra Bernhard.