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David Letterman once creepily tried to pressure Madonna into kissing a stranger — it didn't end well

"I can't. He's not tall enough," the iconic singer said while trying to change the awkward topic.

Madonna has pulled off many cringe controversies since her time as a pop icon in the entertainment industry. However, her 1994 appearance on the 'Late Show With David Letterman' still garners attention for her unabashed usage of cuss language and bizarre cigar moment. The pop culture moment has been dubbed 'infamous' because right from their awkward introduction the seasoned host threw Madonna into an uncomfortable position. "Oh come on let's go kiss a guy in the audience why don't you go kiss the guy in the audience," Letterman signaled the 'Like a Prayer' hitmaker as soon as she settled down on stage. "Why are you so obsessed with my sex life," Madonna instantly shut down the request. 

"Well go kiss the guy in the audience it would knock him out look at that guy just like on the forehead on the forehead," Letterman continued to invade her privacy while the camera spotlighted a stranger. "I can't. He's not tall enough," she resorted trying to change the topic. "I like that she said I can't. A lot of people would cave into the pressure and say 'Oh all right'  they'd go out and kiss him and get it over with," Letterman joked. "Yeah well I've never succumbed to peer pressure," Madonna replied visibly annoyed. "Yeah good for you that's what we love about your mother," the television host mocked. Madonna then lost her cool and insulted the seasoned comedian with the F-word, "Yes whatever personally you are a sick f**k." 

As per The Things, throughout the squirmy introduction, the 'Material Girl' singer demonstrated her discomfort by sitting defensively and crossing her arms over her chest. According to Cheatsheet, the Grammy winner was so riled up during their interaction that she ended up cussing the host a total of 14 times making it the most censored interview in television history. It was reported that the studio audience was displeased by her attitude and manhandled her backstage. She even compelled Letterman to extend the segment by continuing to stay put in her seat.

Madonna accepted that she was in a 'gangsta mood' that day while addressing her controversial behavior on 'The Howard Stern Show' in 2015. She confessed to dating Tupac Shakur during the 1990s which even shocked Stern. “I was in a weird mood that day,” she revealed referring to her bold persona back then. “I was dating Tupac Shakur at the time, and he had got me all riled up about life in general. So when I went on the show I was feeling very gangster.” Shakur's friend Snoop Dogg confirmed their relationship while appearing on Stern's show in 2018. “He shows up with Madonna, man,” Dogg recounted. “He tells her, ‘Have a seat.’ She looks at me, I look at her, [and] I say, ‘Oh wow! That’s Madonna!'”

However, the almost 'power couple' ended things after Shakur wrote a letter to Madonna saying that he didn't want to date a white woman. “For you to be seen with a Black man wouldn’t in any way jeopardize your career. But for me, at least in my previous perception, I felt due to my ‘image’ I would be letting down half of the people who made me what I thought I was,” he wrote while trying to uphold the honor of the black community. “I never meant to hurt you.”