Madonna had no qualms flirting with Johnny Carson in resurfaced 1987 interview: “It should be you...”
Before Madonna became the queen of controversial talk show moments, she had her first-ever late-night interview with the legendary Johnny Carson in 1987. This appearance marked the beginning of Madonna’s flirtatious and rebellious presence on television. The conversation was filled with playful banter and an iconic moment where Madonna coyly suggested that Carson should be the one to “present her as a virgin.” As the interview kicked off, Carson welcomed her on the show and complimented her outfit, “Now that is a nice outfit,” prompting Madonna to laugh and thank him.
The host then curiously inquired about her indulgence in designing her wardrobe. Madonna explained that while she collaborates with designers for performances and films, the outfit she was wearing that night was simply something she had bought at a lingerie store. This nudged Carson to ask hesitantly, “Well, no, I may not be up on these things exactly, but what would you…Yeah, if I went into a lingerie shop and I wanted to buy one of those for somebody, not for me but for somebody, what would I call it?” Madonna confidently answered, “It's called a bustier.” Carson repeated the word marvelling, “A bustier... oh that's nice sounds good doesn't it.” The most unforgettable moment came when Carson acknowledged that he had not seen Madonna on so many talk shows, “I think I want to thank you for coming here tonight I don't see you very often on television except notices one of your specials I saw your 'Saturday Night Live' once in several years ago you were excellent in that.”
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To which she admitted, “Thanks, it's fun. I don't think this is the first talk show I've ever done.” Surprised, Carson followed up, wondering if she felt uncomfortable in such settings. Madonna, in her signature provocative style, responded, “No, I don't feel uncomfortable I just I don't I never thought about doing one but I figured if I was gonna present myself as a virgin to anyone it should be you.” The composure left Carson visibly flustered, nervously trying to maintain composure asserts, “No way all right suppose there has to be a first in my life I'm going to run” Madonna teased him further, “The first girl you spoke to of a bustier.” Carson, still recovering, confirmed, “Yes, I think you are, yeah at least on television, yes on television.”
Fast forward to the ‘90s, and Madonna’s talk show appearances only became more legendary. During a 2015 interview with Howard Stern, Madonna confirmed she had dated Tupac Shakur, revealing that he had inspired her infamous 1994 interview with David Letterman. Stern asked if she liked Letterman, noting that she seemed flirtatious. Madonna clarified, “That’s how I flirt with people…Well, one time I was mad at him when I said the F-word a lot…I was in a weird mood that day. I was dating Tupac Shakur at the time, and the thing he got me all riled up on life in general. So when I went on the show, I was feeling very gangsta.” Her 1994 Letterman interview became the most censored in talk show history, featuring 14 F-bombs, risqué innuendos, and an outright refusal to leave the stage, as reported by Daily News.
Letterman introduced her with a provocative remark about her dating history, setting the tone for an explosive conversation. Madonna presented him with her underwear, smoked a cigar, and refused to adhere to commercial breaks. As per People magazine, Letterman sarcastically remarked, “Coming up in the next half hour, Mother Teresa is going to drop by. Oh, I see we’ve been canceled; there is no show tomorrow night.” Madonna later admitted she regretted the backlash but was ultimately glad she did it. She confessed, “David Letterman knew I was going to do it. I talked to the producers of the show. Everybody was like, this will be really funny if you say ‘f–––’ a lot, and they’ll just keep bleeping you. Well, I came out and started doing it, and David freaked out. The way he introduced me was derogatory, so my whole thing was, okay, if that’s how you want to play it, you cannot beat me at this game.”