Cassius Life Featured Video
2015 Coachella Valley Music And Arts Festival - Weekend 1 - Day 3

Source: Christopher Polk / Getty

Madonna, often referred to as the Queen Of Pop, turns 63 years old today.

She dominated the airwaves for decades and has sold over 200 million albums worldwide. While she worked hard, it’s been documented that she went pretty hard when having fun. Partying aside, she married some pretty famous men in Sean Penn and Guy Ritchie. She’s always been sexually liberated, which came with respect and sometimes controversy.

I think that the world is not comfortable with female sexuality. It’s always coming from a male point of view, and a woman is being objectified by a man – and even women are comfortable with that. But when a woman does it, ironically, women are uncomfortable with it. I think a lot of that has to do with conditioning,” she told Harper’s Bazaar in 2011.

And when it came to relationships, she never discriminated. Here are a few times Madonna was caught thirsting over Black men.

1. Tupac

Interview Magazine party Source:Getty

While many have the iconic photo of Madonna and Tupac chilling at a white tablecloth-clad table, many don’t know the story behind the two music legends’ relationship. It turns out the two dated for about a year in 93-94. Race played a role in the break as the love affair didn’t last long as ‘Pac wrote in a love letter,  saying that her being seen Black man wouldn’t jeopardize her career, but he felt like he’d be letting down his people. 

2. Dennis Rodman

Courthouse... Source:Getty

If you watched The Last Dance documentary, which detailed the rise and fall of the 90s Chicago Bulls, you’ve already got an inkling of how wild Dennis Rodman can get. Unfortunately, that wildness spilled over into his romantic life, which included a brief relationship with Madonna. Upon meeting, she allegedly locked him in her hotel room, refusing to let him about and would eventually offer him millions to impregnate her. Yikes.

3. Drake

2015 Coachella Valley Music And Arts Festival - Weekend 1 - Day 3 Source:Getty

While Drake and Madonna never actually dated, she did kiss him in front of thousands of people while at Coachella. Drake’s got a song called “Madonna” on his 2015 mixtape If You’re Reading This It’s Too Late and had the pop icon perform with him, despite not expecting the kiss. 

“What the f–k just happened?” he exclaimed after the moment before eventually posting a picture of the kiss to his IG with the caption “Moments to write home about 😂 🙏”

4. Big Daddy Kane

Big Daddy Kane Promotional Visit In Chicago Source:Getty

As if the 1990s couldn’t get any more chaotic for Madonna, she also shot a very NSFW photoshoot alongside Naomi Campbell and Juice Crew’s Big Daddy Kane. Back in 2014, Kane spoke about his relationship with Madonna, and the funniest part of the interview came when Madonna revealed to him that the photoshoot would be in the nude.

“Sh-t, even better!” Kane said.

The photos would later appear in Madonna’s book titled Sex, which would sell over 500,000 copies.

5. Jean – Michel Basquiat

Jean - Michel Basquiat at the surprise birthday party for Susanne Bartsch at the Rainbow Roof, at Steven Greenberg's office, 30 Rockefeller Plaza Source:Getty

Despite her run in the 1990s, please know that Madonna was still living her best life in the 1980s with none other than famed artist Basquiat. While not much was known of the relationship, things ended pretty terribly with him making her return all the gifts he gave her.

“When I broke up with him, he made me give [the paintings he gave me] back to him. And then he painted over them black,” Madonna said of the bitter breakup.