Tell me about getting the job on True Blue by Madonna.
That was producer Stephen Bray. I’d been writing with him. I knew he knew Madonna, and I wanted to write a song for Madonna. He was producing True Blue and invited me to come and record. That’s how I met Madonna.

What was she like?
She was awesome, and she was stunning. No makeup. Straight-up beautiful. She was ridiculously youthful and gorgeous. And she was fun to sing with. She appreciated good singers, so she let me and the other singers do our thing.

Stephen Bray said, “We’re going to do this song ‘Where’s the Party’ and we’re going to need you to hire another singer.” I hired this girl that I knew and loved a lot. She had perfect pitch. Her name was Edie Lehmann. I hired her and I looked at Madonna and said, “Do you want to sing on this?” And so I hired Edie Lehmann and Madonna for Madonna’s record. [Laughs.]

What do you recall about making “Papa Don’t Preach”?
I thought the song was very edgy. I knew it was going to be controversial. That was Madonna’s thing at the time. She loved controversy. This song was like an ode to pregnant teenage girls all over the world and telling their parents that they “got into trouble.” Her doing this was very edgy and brave, I thought, and it worked.

To jump forward a bit, can you tell me how you wound up on the Madonna Re-Invention tour?
I was having lunch by myself, as I often did at that time, at a very fancy restaurant, having a sushi lunch in the private dining area, which is only, like, six feet, so it was just me. And in walks Madonna and Guy Ritchie. Madonna goes, “Hey, Siedah!” I go, “Hey, Mrs. Ritchie!” That made Guy go, “Hey, this is different.” His whole time with her was probably, “Madonna! Madonna! Madonna!”

Madonna goes, “How have you been? What have you been working on? What are you doing?” When she said, “What are you doing?” I said, “I’m waiting for Donna to fuck up so I can take her place.” Donna De Lory is the backup singer that was on Madonna’s [Drowned World] tour with [backup singer] Niki Haris.

We finished our lunch and both left. About two years later, I get a call. “Hey, you still interested in going on the road?” “Yes!” And so I auditioned so they could see if I could do the steps, or whatever. I ended up on the Re-Invention tour. But I didn’t replace Donna De Lory. I replaced Niki Harrs. I had no hand in that.

Madonna is the hardest-working artist that I’ve ever worked with. She knows her limitations. And she’ll be the first to tell you, “Look, I’m not the best singer. I’m not the best dancer.”

But let me tell you what this bitch is the best at. Madonna is the best at marketing Madonna. Her fans love her, and all she has to be is herself. That is the best kind of artist to be since you can just be free and still have the support of your fans, which she does. It was awesome. It was like working with Michael on a slightly different level.

One of the biggest differences between Michael Jackson and Madonna is that with Michael, we rehearsed for three months and then we didn’t see him until we were on the stage. With Madonna, we rehearsed for three months, and we rehearsed after every show.

It must have been fun to sing “Papa Don’t Preach” and those old songs with her again.
Yeah. It was really helpful because you didn’t have to sing much since her fans sang all her stuff. It was fun and interesting to hear them sing her songs back to her, and she loved it. She also gave me a feature. I stepped out on “Like a Prayer.”

What was that like?
To have her “endorse” you as a singer was awesome. Her fans wanted to know who I was when they saw me with her. They never put the two and two together besides the savvy ones that saw my name on the True Blue album and put it together. But she let me do a step-out and she helped me, had her arms around me the whole time. She wanted everyone to know, “I approve of this girl.” She let them know by being very physical with me onstage, where the other singers she was just in line with them. It didn’t appear to the audience that she had that deep a connection with them as she did with me.

Read the full interview on Rolling Stone