Who: Grammy-award-winning singer (and the ultimate "Material Girl"), Madonna, 63, and the beloved West Coast rapper and Hip Hop Hall of Fame inductee, Tupac Shakur, who tragically passed away at the age of 25. He would've turned 51 this year.
How They Met: While Madonna is sly about the details, Rosie Perez claimed she played matchmaker for the couple in an 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. (Stars, they're just like us!)
"I went to the Soul Train Music Awards ... and then Madonna comes over and looks at me and she goes, 'Girl,'" Perez shared. "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." And thus, a music power couple was born.
Why We Loved Them: 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 Tupac 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) after his performance. As Snoop tells it, "Guess who he pulls up with?" Snoop then revealed that the surprise guest was Madonna, singing "Like a Virgin." "[Madonna] was just riding along for the ride," he added.
Ah, to be a fly on the wall for what must've been an iconic SNL afterparty.
When They Peaked: Because the relationship between Madonna and Tupac was secret at the time, there aren't a lot of public details about their romance. In fact, Madonna didn't confirm that they even dated until a 2015 Howard Stern Show appearance. In reference to a tense 1994 David Letterman interview, Madonna attributed her mood to the late rapper, according to MTV. "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.
As music lore has it, the couple also recorded a song together as part of Madonna's Bedtime Stories album. The singer confirmed the existence of an unreleased track in 2018, when she teased fans on Instagram with a post honoring the late rapper.
"One day I will release the song we did together!" she said. We're still waiting to hear the track, but here's to hoping that Tupac x Madonna collab drops on Spotify soon.
The Breakup: Until recently, skeptics remained unconvinced about the nature of Madonna and Tupac's relationship: Was it more than just a fling? And 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 — dated January 15, 1995, at 4:30 a.m. — written by the rapper 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 Tupac 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. 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 ends 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."
Where They Are Now: Since her break with Tupac, Madonna has become a mother to six children: Lourdes Leon, Rocco Ritchie, David Banda, Mercy James, Stelle Ciccone, and Estere Ciccone.
The pop icon also went on to win countless awards, release several albums, and perform like a true music legend well into her 60s. Her latest, Madame X, was released in 2021.
In 1995, Tupac married his then-girlfriend Kidada Jones, a pre-law student, but their marriage was annulled 10 months later.
The rapper tragically passed away in 1996, but his musical legacy lives on. Since his untimely death, seven posthumous albums have been released from his musical archives, and Shakur was inducted into the Hop Hall of Fame in 2002.
#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.