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When it comes to the music industry, does it get more iconic than Madonna or Tupac Shakur? Well, you might be surprised to find out that these legendary musicians had a brief relationship in the ’90s. Let’s take a look back at this oft-forgotten coupling.

They Reportedly Met In 1993

While Madonna hasn’t given away many details about her and Shakur’s romance, actress Rosie Perez once claimed that she introduced the two. During an interview on The View, Perez revealed she was spending time with Shakur at the 1993 Soul Train Music Awards when Madonna approached her.

“I went to the Soul Train Music Awards … then Madonna comes over and looks at me and she goes, ‘Girl,’” the Fearless star remembered. “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.”

The Two Dated For At Least A Year

Both Madonna and Shakur stayed tight-lipped about their romance. However, it seems like their secret romance lasted over a year. While Rosie Perez insists the two got together at the 1993 Soul Train Awards in March of that year, other accounts of the couple’s relationship put them still together around May of 1994.

Snoop Dogg told Howard Stern in 2018 that when he hosted Saturday Night Live in May of 1994, he called Tupac Shakur asking if he could bring him some weed. According to the rapper, Shakur proceeded to drive up to NBC headquarters with Madonna in the car.

Madonna Confessed To Dating Tupac In 2015

We shouldn’t be surprised that Stern has gotten most of the tea about Madonna and Shakur’s private romance. In a 2015 appearance on the Howard Stern Show, Madonna off-handedly admitted to dating the legendary rapper.

Initially, Stern asked Madonna about a tense 1994 interview with David Letterman. Unprompted, the “Like a Virgin” singer revealed that she was so moody because of her then-ongoing relationship with Shakur. “I was dating Tupac Shakur at the time, and the thing is … he got me all riled up on life in general. So, when I went on the show I was feeling very gangster,” Madonna explained, confirming the decades-old rumored romance.

Despite being known for her bold artistic choices and free-spirit personality, Madonna’s romance with Shakur is just proof that she still managed to maintain a private life during her many, many years in the spotlight. While we’ll probably never know the full story of their romance, just knowing it happened certainly changes how we look at the early ’90s music scene!

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