Over two decades after Madonna’s eyebrow-raising interview with David Letterman, the pop star revealed that there were two factors that influenced her on-air misbehavior. “One time I was mad at [Letterman] when I said the f-word a lot, but the rest of the time was good,” the “Justify My Love” singer said on “The Howard Stern Show” in 2015 (via E! News). Plus, she blamed her outbursts on a romantic relationship she was in at the time of the appearance. “I was in a weird mood that day. I was dating Tupac Shakur at the time, and he had got me all riled up about life in general,” Madonna said. “So, when I went on the show I was feeling very gangsta.”
Shortly after Madge let the cat out of the bag that she had dated Shakur, Rosie Perez said that she played matchmaker for the two music stars. On an episode of “The View” in 2015 (via The Hollywood Reporter), Perez said she introduced Shakur to Madonna at the 1993 Soul Train Music Awards. “I hooked it up, and I was very happy about it,” the actor said.
That same year, the “Hit Em Up” rapper’s brother, Mopreme Shakur, spoke about his late brother’s relationship with Madonna. “They were kickin’ it. I don’t think it was super serious going to get married or some s***,” he said in a 2015 interview for VladTV. While Tupac’s brother did not think the relationship was serious, the rapper regretted the way his romance with Madonna ended.
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