Madonna’s Infamous David Letterman Interview Happened After Tupac Shakur Got Her ‘Riled Up’ to be ‘Gangster’ on TV

Madonna has been a pop culture icon for decades. After rising to fame and becoming a household name in the 1980s, Madonna was the beloved Queen of Pop as her popularity and success continued into the ’90s. At one point, she was romantically linked to legendary rapper Tupac Shakur — something that she claimed affected her behavior during one unforgettable interview with David Letterman.

Madonna had an infamous appearance on ‘The Late Show with David Letterman’ in 1994

Madonna stopped by The Late Show with David Letterman on March 31, 1994 for what would become a headline-making interview. Her contempt for Letterman was apparent from the moment she sat down, as she wasn’t entertaining any of his sexual innuendos and suggestive comments.

The interview was most notable for Madonna’s use of swear words throughout her time on stage. She said “f***” a total of 14 times throughout her interview, making the episode the most censored episode in American network TV talk show history. Letterman’s show, meanwhile, earned a massive ratings boost as a result of Madge’s antics.

Behind the scenes, Madonna faced heckling from audience members who were displeased with her attitude and her language. She even refused to get up from her seat once the interview was over, and forced Letterman to continue speaking to her in subsequent segments.

Tupac ‘riled up’ Madonna to act ‘gangster’ on TV

Madonna reflected on the interview in a 2015 appearance on The Howard Stern Show. She admitted that she was in a wild mood on March 31, 1994 because of her dealing with rapper Tupac Shakur, whom she was in a relationship with when she went on the show.

“I was in a weird mood that day,” she said. “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.”

Snoop Dogg, who was a close friend and labelmate of Tupac, recalled Pac’s relationship with Madonna in a 2018 interview on The Howard Stern Show. Snoop was at Saturday Night Live back in the ’90s and looking to buy weed from Tupac, and the iconic rapper showed up to the set with the “Like a Virgin” singer in tow. “He shows up with Madonna, man,” he remembered. “He tells her, ‘Have a seat.’ She looks at me, I look at her, [and] I say, ‘Oh wow! That’s Madonna!'”

Tupac broke up with Madonna because of her race

Their relationship would only last the better part of a year. In January 1995, Tupac wrote Madonna a letter from jail explaining that he had to break off their relationship. But it wasn’t irreconcilable differences that drove them apart; Tupac felt that he had a duty to make the Black community proud with his actions, which included not dating a white woman like Madonna.

“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, according to TMZ. “I never meant to hurt you.”