Madonna and Tupac Shakur's Relationship Timeline: A Look Back

May 2024 ยท 4 minute read

Remember when Madonna and Tupac Shakur dated? No? Well, that's probably because the relationship between the Grammy-winning singer and the beloved "California Love" rapper was a secret at the time (they met in 1993 when Madonna was 34 and Tupac was 21). 

As such, there aren't a lot of public details about their romance. In fact, Madonna didn't confirm that they even dated until she appeared on The Howard Stern Show in March 2015. In reference to a tense 1994 interview on The Late Show with David Letterman, the "Material Girl" attributed her 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." With that admission, Madonna finally confirmed the long-rumored romance.

Here's a look back at Madonna and Tupac Shakur's relationship.

March 1993: Madonna and Tupac Shakur first meet

While Madonna is sly about the details, Rosie Perez claimed she played matchmaker for the couple during a 2015 interview on The View. Perez and Shakur attended the 1993 Soul Train Music Awards together as friends after she had been ghosted by her date. 

"I went to the Soul Train Music Awards ... and then Madonna comes over and looks at me, and she goes, 'Girl,'" Perez revealed. "I said, [to Tupac] 'She wants to meet you,' and he goes, 'Hook that up.' And I hooked it up, and I was very happy about it." Thus, a music power couple was born.

March 1994: Madonna and Tupac Shakur are first spotted together โ€” by Snoop Dogg

Besides the obvious icons-dating-icons appeal (their collective musical talent is unmatched, after all), we can only imagine the mid-'90s hangs they must've been a part of. Take, for instance, the time that Snoop Dogg performed on Saturday Night Live in 1994.

The rapper told Howard Stern that Shakur was also in New York at the time. 

"He was like, 'What's up, where ya at?'" 

Naturally, Snoop invited the rapper to come by (and deliver some weed, according to Vulture) after his performance. 

Snoop quizzed the panel, "Guess who he pulls up with?" before revealing that the surprise guest was Madonna and singing "Like a Virgin." 

"[Madonna] was just riding along for the ride," he added.

January 1995: Madonna and Tupac Shakur break up

Eric Weiss / WWD / Penske Media via Getty Images

Until recently, skeptics remained unconvinced about the nature of Madonna and Shakur's relationship: Was it more than just a fling? With so few public moments together, it was difficult to say.

In 2017, however, after years of rumors and murky details, we finally got our answer. A letter โ€” dated January 15, 1995, at 4:30 a.m. โ€” written by the Hip Hop Hall of Fame inductee to the "Vogue" singer confirmed the depth of their romance. In an excerpt of the note released by TMZ, Shakur mentions a disagreement between the couple and the tension Shakur felt about dating a pop star.

"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 explained in the letter. The rapper then described their breakup as a consequence of the pressure being in an interracial relationship might put on his music career.

However, the letter ended amicably, suggesting that the stars left things on a good note: "I don't know how you feel about visiting me, but if you could find it in your heart, I would love to speak face to face with you. It's funny, but this experience has taught me to not take time 4 granted."

2018: Madonna confirms she recorded a song with Tupac Shakur

As music lore has it, the couple also recorded a song as part of Madonna's 1994 Bedtime Stories album. The singer confirmed the existence of an unreleased track in 2018, saying, "One day, I will release the song we did together!" 

We're still waiting to hear the track, but here's to hoping that Madonna and Shakur collab will drop on Spotify one day.

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