June 1990; photographed by Herb Ritts.
"The idea that the first guy I ever slept with, my lover when I was fifteen, is married and has kids really breaks me up. I wonder if he still loves me. He probably does."
May 1989; photographed by Koto Bolofo.
"For a while I was obsessed with being a nun. I just thought they were so superior. Then, when I realized that nuns didn't have a sex life, I was incredibly disenchanted."
December 1985; photographed by Herb Ritts; designed and painted by Richard Bernstein.
"When I was a child I always thought that the world was mine, that it was a stomping ground for me, full of opportunities. I always had the attitude that I was going to go out into the world and do all the things I wanted to do, whatever that was."
January 1992; Chuck Close: Self-portrait (119); oil on canvas/The Pace Gallery. Magic Johnson: Andrew Eccles/Outline. Madonna: AP/Wide World Photos.
"Madonna is the embodiment of the modern woman of legend. Instead of being stultified as an object, Madonna is a trailblazer who has confronted prejudice, smitten the obstacles of convention, and distorted boundaries into challenges with the power of her will and inspiration." —David Geffen
March 2001; photographed by Jean-Baptiste Mondino.
"I feel that I was certainly a victim of snobbery when I first started. I can't even count the number of things that I read about myself that kept dismissing me. And dismissing the fact that I had talent or that I could sing or any of those things."
April 2008; photographed by Steven Klein.
"When you live in the world that we live in, and you have the luxuries that we have and the privileges that we have, you don't have to worry about basic needs and you can start thinking about, What am I slave to? What am I trapped by? Am I really free? Just because I can get on a jet and fly wherever I want and I can afford this and I can afford that—is that real freedom?"
May 2010; photographed by Jean-Baptiste Mondino.
"I'm going to have to reinvent the wheel. I haven't really been focused as much as I should be on the music part of my career because this movie has just consumed every inch of me. Between that and my four children, I don't have the time or the energy for anything else."
June 1993; photographed by Herb Ritts.
"I think that everyone should get married at least once, so you can see what a silly, outdated institution it is."