Why Madonna Blames Tupac For Her Infamous Letterman Interview

One of the most infamous late night appearances of all-time was Madonna's controversial appearance on "The Late Show with David Letterman" in 1994. The "Human Nature" singer was feeling particularly frisky and let loose a string of expletives, including 14 F-bombs. She also made numerous sexual innuendos when speaking with Letterman, and refused to leave the stage even after the host tried to cut the segment short. Initially, Madonna was remorseful for how she behaved, as the "Late Show" appearance became front page news. "I regretted it right afterward because of the reaction. I couldn't believe how freaked out people were," the singer told Spin in 1996 (via People).

However, the "Take a Bow" artist said that the host was made aware ahead of time about how she would act. "David Letterman knew I was going to do it. I talked to the producers of the show," she told Spin. Shortly after the taping, Madonna wrote a handwritten note to Letterman, and claimed the incendiary reaction to her behavior was because she was a female. "In this country you are not allowed to be a girl, look good, have a point of view and have a good time all at once," she wrote, per TMZ.

Despite the note to Letterman, Madonna told Spin that she had no regrets about her lewd on-air behavior. In fact, Madonna later revealed that Tupac Shakur was partly to blame for the nefarious TV appearance.

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.

Perhaps Madonna and Tupac Shakur's relationship was not overly serious, but allegedly, the "Nothing Really Matters" singer was in a hurry to start a family around the time the two dated. "In her mid-30s Madonna desperately wanted children and had various relationships with unlikely men, in the hope she would conceive," author Lucy O'Brien wrote in her 2007 biography "Madonna: Like an Icon" (via Stuff). The author also spoke to a friend of Madonna's — Alison Clarkson — who claimed Shakur broke things off with her due to racial differences. "She was going out with him but homegirls were saying to him, 'I can't believe you're going out with a white girl,' so she got dumped!" Clarkson told O'Brien. 

A letter written by the "All Eyez On Me" artist to Madonna while he was incarcerated seemed to back up the friend's claims. "For you to be seen with a black man wouldn't in any way jeopardize your career, if anything it would make you seem that much more open and exciting," Shakur wrote in the letter that was auctioned in 2017, per TMZ.

The rapper mentioned how quotes from a previous interview with Madonna caused him to lash out at her. "Those words cut me deep," Shakur wrote while explaining that he had acted out of emotion, per TMZ. In the handwritten note, he was eager to make amends with the "Vogue" singer. "I felt compelled to tell you ... just in case anything happened 2 me," Shakur added.