For years, Big Daddy Kane fans wondered what exactly was up with him and Madonna.

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Rumors definitely started to swirl when the “R.A.W.” rapper, got all the way raw with her in the 1992 book, SEX.  Especially when it was revealed that she and Tupac had a brief fling, it is quite plausible that she shot her shot with when she included him in her first literary project.

The photo book explored sex on all types of levels and was considered explicit and pornographic in the 90s. Kane didn’t help. In his spread, he played boy toy to Naomi Campbell and Madonna for some of the most erotic portrayals of art that Hip-Hop had ever seen at the time.


READ MORE: Exclusive: Big Daddy Kane Talks Battling in NYC, Discovering JAY-Z and More

A more mature Kane looks back on that time in his life, and finally tells fans if the “Material Girl” was trying to kick it to him.

The Source: When did you transform from a battle rapper to a sex symbol?
Big Daddy Kane: I guess after the records. When we start putting songs out I guess the female audience changed the whole perspective. It turned into something else.

Was it a conscious thought or an evolution of your person?
Well…  growing up I was ugly because I was dark-skinned. So I wasn’t used to women hollering at me and saying that I was fine. So that was some new shit when I started making records. I was like “Oh, word!!!” (laughter) I grew up in the LL Cool J/ El Debarge era. So I was like “Oh, word? I’ll take it.”

And then the book….
Oh, Madonna?

Did she holler at you? Was she like “I need to talk to you.”
We were doing a promo tour for Warner. Bros. But it was in an upper-class hospital. And you know the white kids in the hospitals were sick, they didn’t know who I was. They recognized Madonna and Color Me Badd. And Madonna was talking to them and was like, “This is Big Daddy Kane, a famous rapper. Let me hear you say ‘Ain’t No Half Steppin’” And I am like “Wow… Madonna knows my shit.” She was just showing love. She saw what the situation was, and that I shouldn’t have been there. But then afterward, she told me she was doing a book and she thought that I was attractive and she would like for me to be in it. And I was like “I would be honored.” And she was like “but its gonna be nude photos.” And I was like “Shit… even better.” (Laughter)

Did she try to holler?

Why not?
Or if she did, I didn’t know. I mean.. she was just rather friendly. You know when I go there to the photoshoot… Me, her and Naomi Campbell…

She tried to holler…
I mean we in photos with my finger up inside of her and she never said “Yo… put something else it.”  If that was a chance for her to shoot her shot… what better time than that? So, I don’t think she tried to holler.

So what happened when you got back to Brooklyn? Did your friends look at you differently?
The people that got love were like “That’s amazing. This dude is up there with ‘Borderline.’ Wow!” And then you had the haters who were like “what you doing with that white woman? You selling out. That’s pop stuff.”  But those same people are gentrified like a mf now.

Guess, she kept her composure and didn’t get some of Mr. Chocolate.