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Tupac Shakur Performance At The Palladium NYC

Source: Al Pereira / Getty


Madonna surprised the world in 2015 when she revealed during an interview with Howard Stern that she had once dated Tupac Shakur. The radio host asked the singer about a contentious interview she once had with David Letterman in the ’90s, and Madonna attributed her sour mood to the late rapper. “I was dating Tupac Shakur at the time, and the thing is he got me all riled up on life in general,” she said. “So, when I went on the show, I was feeling very gangsta.”

Despite the big reveal, many remained skeptical whether or not her relationship with Shakur was more than just a fling. But let the record show: A newly revealed letter from the rapper to the pop icon sheds new light on the reality (and depth of feeling) of their romance. Dated January 15, 1995, at 4:30 a.m., the letter, published in part by TMZ, was written during Tupac’s stint in prison at the Clinton Correctional Facility. The three-page love letter, which is partially redacted, mentions a fight that took place between the two of them and the pressures that Tupac felt while dating someone as famous as the Material Girl.

“First and foremost, I must apologize to you because, like you said, I haven’t been the kind of friend I know I am capable of being,” he wrote. “An interview where you said ‘I’m off to rehabilitate all the rappers & basketball players’ or something to that effect those words cut me deep seeing how I had never known you to be with any rappers besides myself. It was at this moment out of hurt & and natural instinct to strike back and defend my heart & ego that I said a lot of things.” Read the full story here.

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