LIFE LESSONS

Life Lessons: Four Decades of Madonna and Interview

Welcome to a special edition of Life Lessons. This week, in celebration of the release of Madonna’s Finally Enough Love Remix Album, we’re revisiting every one of our cover stories featuring the Queen of Pop. Madonna has graced the cover of Interview 10 times—more than any other star in our history. And we’re not the only ones digging through the archives—now, thirty five years after the release of her record-breaking remix album You Can Dance, the Material Girl has compiled all 50 of her No. 1 singles (the most of any artist in recording history) into a something-for-everyone album to commemorate the 40th anniversary of her recording career. So sit back and listen up—you just might learn a thing or two.

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December 1985

Madonna

Madonna photographed by Herb Ritts for Interview.

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“People who believe in dreams and magic and things that are happy. Life is so real and grim.” 

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“I don’t take myself too seriously. I think that’s a quality that people have to hold onto, you have to laugh, especially at yourself.” 

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“America is a really life-negative society. People want to know all the underneath stuff, your dirty laundry.” 

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“Ultimately, anybody who sits around predicting the failure of anyone else is fearing his own failure.” 

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May 1989

Madonna

Madonna photographed by Koto Bolofo for Interview.

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“I wanted to chase after boys on the playground, but the nuns told me I couldn’t, that good Catholic girls don’t chase after boys.” 

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“I moved to New York when I was seventeen, and I had lots of terrible moments. I was afraid, I didn’t know if I’d done the right thing, I missed my family, and then I’d say, “Well at least I don’t have to go to Church every Sunday.”

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“The pitfalls of the women’s movement was that women wanted to be like men… to have power… I think that’s bullshit. I think women have always had the power, they just never knew it. You can be just as powerful being feminine.” 

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“I think the most interesting men I’ve met are the ones who are in touch with their femininity. I dislike men who suppress their femininity.”

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“Sadness is a teacher, and happiness is really a gift.” 

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“Love is like breathing. You just have to do it.” 

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June 1990

Madonna

Madonna photographed by Herb Ritts for Interview.

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“I do think someone is protecting me. I don’t know if it’s an angel. It could be the devil.”

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“Guys get to do everything. Take their shirts off in the summer. They get to pee standing up. They get to fuck a lot of girls and not worry about getting pregnant.” 

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“I like the idea of men being the objects of desire, the sirens that entrap women.” 

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January 1992Madonna

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June 1993

Madonna

Madonna photographed by Herb Ritts for Interview.

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“I think that everyone should get married at least once, so you can see what a silly, outdated institution it is.”

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“We’re all prostitutes in our own way.”

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March 2001

Madonna

Madonna photographed by Jean-Baptiste Mondino for Interview.

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“Our generation has certainly been encouraged to grab life by the balls, be super independent, get a great education, follow your dreams, kick ass, all that stuff.”

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“I woke up one day holding the golden ring, and realized that smart, sassy girls who accomplish a lot and have their own cash are independent and really frightening to men.”

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“You forgive people a lot when you’re distracted by how gorgeous they are.”

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April 2008

Madonna

Madonna photographed by Steven Klein for Interview.

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“If we are going to save the world, can we please have a good time while we’re doing it?”

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“It’s all rather confusing. Ultimately we’re fighting the same disease, but it’s a question of consciousness and where your head is at. And for most people around the world, our heads are up our asses.”

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“We live very comfortable lives and, unfortunately, we have to have our noses rubbed in other people’s pain and suffering to realize how much we have and how much we have to be grateful for, and to tune into that frequency of appreciation.”

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“When I stop thinking about myself all the time and put other people before me on a regular basis, that’s real freedom.”

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“When people are busy making music and dancing, they’re kind of too busy to hate and fight. Music is one of the great unifiers.”

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“Oh god, you know, I can’t deal with America.”

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“When people have to work to get somewhere, you know they really want to be there.”

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“Certain things happen, and there isn’t a doubt in your mind. You know there’s going to be challenges, you know that it’s going to be a rocky road and all of those things, but you also know in every cell in your body that it’s the right thing to do, so you just do it.”

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“Do not tell me who I should love, or how I should love.”

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February 2010

Madonna

Madonna photographed by Jean-Baptiste Mondino for Interview.

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“I quite like the idea of collaborating in general. Not only is it lonely to do things on your own creatively, it’s also kind of arrogant.”

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“But you know, what the movie [Milk, 1998] triggered for me was all my early days in New York and the scene that I came up in with, you know, Andy Warhol and Keith Haring and Jean-Michel Basquiat and Kenny Scharf. It was just so alive with art and politics and this wonderful spirit. So many of those people are dead now. I think that’s one of the reasons I cried.”

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“The character that Richard E. Grant plays in the film I directed, Filth and Wisdom (2008), is this blind professor who was based on my ballet teacher, Christopher Flynn. Growing up in Michigan, I didn’t really know what a gay man was. He was the first man—the first human being—who made me feel good about myself and special. He was the first person who told me that I was beautiful or that I had something to offer the world.”

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“I think it’s good to get into arguments with people and have them say, “you’re crazy” or “that’s cheesy.” If anything, it helps you understand what you believe in.”

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“It’s curious, because it seems like those days are really over in the music business, where guys like that ran things, or where you could go and see a band and get so inspired and discover them and make records with them. It’s kind of sad.”

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December/January 2015

Madonna

Madonna photographed by Mert & Marcus for Interview.

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Madonna photographed by Mert & Marcus for Interview.

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“I remember having conversations with Keith [Haring] and Basquiat about the importance of your art being accessible to people. That was their big thing—it should be available to everyone. It was so important for Keith to draw on subways and walls. Basquiat used to say to me, ‘You’re so lucky that you make music, because music comes out of radios everywhere.’ He thought that what I did was more connected to pop culture than what he did. Little did he know that his art would become pop culture.”

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“I was attracted to creative people. You don’t want to be the smartest person in the room, you want to be the dumbest in the room. You want to be surrounded by other thinking people who are going to say something that makes you think, ‘Oh, my god that’s an amazing idea. Why didn’t I think of that?’”

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“I mean, Basquiat was my boyfriend for a while, and I remember getting up in the middle of the night and he wouldn’t be in bed lying next to me; he’d be standing, painting, at four in the morning, this close to the canvas, in a trance. I was blown away by that, that he worked when he felt moved.”

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“But that’s our job. We’re in the world of creating illusions and giving people the ability to dream and to be inspired or moved. So you don’t want people to see the labor behind it. Also I was trained that, as a dancer, no matter how much you’re suffering, your face is relaxed.”

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September 2015

Madonna

Madonna photographed by herself for Interview.