Donna DeLory spills on 20 years working with Madonna, Blond Ambition shenanigans & if a reunion is in the cards

On this day 65 years ago, a queen was born.

As Madonna celebrates another trip around the sun and prepares to embark on her Celebration Tour, which kicks off in London on October 14 and will feature all her biggest hits from the last 40 years, we’ve been feeling extra nostalgic.

Her world domination began around this time in 1983, which the release of her self-titled debut album, and has continued ever since.

The apex of her career, of course, was in the late ’80s and early ’90s, when she was cranking out hit after hit after hit, traveling the world, making movies, and on the front page of virtually every newspaper and magazine cover.

And Donna DeLory was there for it all.

She first started working with Madonna in 1987, singing backup (along with Niki Harris) on the Who’s That Girl Tour, and continued working with her through the Confessions Tour in 2006 before becoming a mom and turning her attention towards her solo career.

We caught up with her Donna to fangirl out about Madonna during this exciting and celebratory time in the pop star’s life, as well as to reflect on her 20 years working alongside the Queen of Pop, and whether a Madonna/Donna/Niki reunion might be in the cards. Here’s what she had to say…

QUEERTY: First question… What’s your favorite Madonna song to sing and why?

DELORY: Wow. To sing background on or lead?

How about both? This can be a two-parter.

It’s so hard because she’s such a great songwriter, really. I love all of her stuff.

Right now, I’m really into “Nothing Really Matters.” I love that it’s a dance song with a message. And “Ray of Light.” Those songs are two of my favorites. I mean, I love all the dark stuff, as well. I love “Live To Tell.” And the ballads and everything. But I really appreciate an uptempo song with a message.

As far as the ones that we did backgrounds on, I mean, “Vogue” was the most fun session. We went in there and we started laying down the part. It was me, Niki Harris, and N’Dea Davenport. And it was such a new sound. It was just so innovative and exciting. Sometimes Madonna would come out and sing with us in the group, so there’s that really nice blend that we all had singing together on the record.

How about your favorite Madonna era?

Like a Prayer. I think because that was, like, when we went out and toured in 1990. We were in the show and it was so demanding, but it was also so rewarding. Plus, we were young, we had so much energy, we could take advantage of the nightlife and the cities were in. It’s not like later on when I was 40 years old touring with her and I had a kid. You know? It was such a specific time. It was a crazy time.

Crazy how?

Because it was, you know, the ’80s and ’90s rock and roll scene. We were all exploring. Out of all the tours, that one felt the most like a family. We all knew what was going on in each other’s lives. You couldn’t hide anything from anyone.

Okay, here’s a crazy thing. It has to do with being in Amsterdam. This was before cannabis was legalized [in the U.S.]. And so going to a shop and buying it was such a concept. We ate like a ton of hash brownies.

Wait, who? You and Madonna?

No! It was not Madonna. Just Niki and me and the crew. We end up getting back to our hotel, and we all go to our rooms because there was a show the next day. So, we’re all in our rooms and all of a sudden I look up and I see spiders crawling on the ceiling and I start losing it. That had never happened to me before! And then I get a call from Niki and she’s like, “Are you seeing things crawling on your walls?” It was a long night. Because now we’re both tripping and then I start realizing, “Oh my god, I gotta pull it together! I’ve got a show tomorrow!”

What was the hardest part about touring with Madonna?

The hardest part for me was just getting enough sleep because I had so much adrenaline after a show. It took me a long time to wind down. Then I’d get to sleep really late and then in the morning I would stumble into Starbucks and get my coffee. You know, it wasn’t singing and dancing, like people say. And it wasn’t even, like, when it was raining and trying to find different ways to do the choreography so you didn’t slip and break your neck. It was getting enough sleep.

Tell me about a mishap or a time when something went totally wrong on tour.

It was the first tour Niki and I did. We were outside, doing stadiums. So, when you’re in stadiums, you got all that wind and everything. It’s so different than being in an arena. And so we’re on the stairs behind these giant blinds that keep swinging towards us and we’re trying to do the “True Blue” thing. And all of a sudden, these blinds are supposed to open and you see us standing there, but they keep blowing in the wind and start getting mangled and twisted. Then they become a whole different shape and they’re coming towards us. And there was always water on the stage. Niki and I would tell Madonna, “We’ve got your back. We’ll be right behind you.” We’d be trying to see if there were any potential hazards when she did her choreography. And sometimes even people throwing stuff on stage could become a hazard. I remember always kicking stuff off the stage.

What is something most people don’t know about Madonna?

I was always so impressed by how well read she is. She really dedicates a lot of her life to reading and learning and just being well-cultured. It meant a lot to her to get other people to read, as well. To inspire people, like all of the dancers. She’s a teacher, you know? She was always talking about the book she was reading. On nights off, we would have documentary film screenings. She really wanted to inform people about different issues, whether it was Michael Moore’s latest film, or oftentimes the films would be about spirituality. I always really appreciated that about her.

The two of you worked together for 20 years. How would you describe your relationship?

It was a very professional relationship. She always made a point to say how professional I was, and to thank me for my professionalism. I took the job seriously and I think she was kind of used to me being there. I always thought that, naturally, she would change singers. And I always thought every time I’d say goodbye at the end of a tour I wasn’t going to do another one. I didn’t count on it, you know? So I was always surprised when I’d be asked back. It was a really good relationship, and she just continues to inspire me with the work she does. I think it’s great.

I have to ask… What are the chances of a possible reunion between the three of you? Madonna, Donna, and Niki. Will we ever see it?

I don’t know. I always had this vision of us doing some kind of huge charity event or a Pride event. I mean, you just never know. But she has so many ideas and new things she’s working on and new people she’s working with. So I totally understand that.

But if she asked?

I would love to. And I think Niki would too. I’m happy that we all share those memories together. We were all at those shows together, witnessing it, and experiencing it. And if it ever happens again, great. It’d be nice reunion, for sure. If it doesn’t, that’s fine as well. I think if somebody presented the idea to her, if she had the influence of, like, a DJ or a certain producer, she’d be open to it. Somebody presenting a concept. For a certain event.

Okay, so let’s put that out into the universe!

Exactly. It would mean a lot to the fans.

Watch the video for DeLory’s “Ma Song” from her solo album Gone Beyond below.

This interview has been edited for length and clarity.