“Is he gay?” asked Madonna. “Gay men take good pictures of me.”

When I worked at the PMK PR firm in 1980, every time we signed a new client, Michael Maslansky (the “M” in PMK) used to have them photographed by Herb Ritts. I’m sure this had more than a little to do with Herb being represented by Michael’s wife Marysa, who had a photo agency called Visages, but the photos were always wonderful. I never met Herb until years later, when I had my own company and was handling Paul Verhoeven’s The Fourth Man. For a photo for “Interview” magazine, Herb tiptoed me and The Fourth Man’s Dutch femme fatale, Renée Soutendijk, up to the roof above the dilapidated structure that sat on the site of what is now Chelsea Piers. It was obvious that we were trespassing, and that made it fun, but you couldn’t help but wonder, “How much time did he spend prowling around all this broken glass and torn metal before finding this perfect spot?”

“I have no idea if Herb Ritts is gay, Madonna,” I said. “But I promise you will like his pictures.” As usual, Madonna was busting my balls, but the important thing was that she and Rosanna Arquette were willing to give up an entire Saturday of shooting Desperately Seeking Susan to do the special photography shoot. Ann Lander, the Orion exec in charge of photography, had assigned Herb to create some portraits that I could circulate to magazines. If all went well, maybe there would be a poster in there too.

But what should the poster be? What would be a solitary image that would capture the story? Desperately Seeking Susan is about a bored New Jersey housewife named Roberta (played by Arquette) who follows the personal ads and is obsessed with a free-spirited woman named Susan who uses the personals to keep in touch with her boyfriend. Roberta decides to follow Susan around, and when Susan sells her jacket at a thrift store, Roberta buys it, setting in motion a mistaken identity plot. Through the jacket (and a case of amnesia), in a lot of ways Roberta gets to become Susan. The jacket is the engine that makes the whole plot go. So I knew I wanted to display the jacket in a significant way in the poster.

Madonna and Rosanna had totally different kinds of bodies, so Costume Designer Santo Loquasto had made two jackets. But nobody was supposed to know that there was more than one—it would defeat the whole purpose. But something told me that having them both of them in the “Susan” outfits was the way to go. It didn’t make literal sense, but I convinced myself it made metaphorical sense: Roberta and Susan were twins, two sides of the same coin, sisters. Each of them stepped into the other’s life and tried it on for size.

Nowadays photo shoots like these are a big deal, with limos for talent and a gaggle of publicists and studio executives, but the only people there besides me were the wardrobe supervisor Melissa Stanton (who brought the jackets, costumes and accessories), Herb’s crew, Madonna and Rosanna, who cabbed over themselves. (Why am I so sure they didn’t get cars? Because afterwards Madonna complained that she couldn’t take the subway anymore. She had only recently reached the level of fame where people hassled her on the trains, and she was pissed off about this intrusion on her freedom.)

Upon my entry to the studio I was greeted by the sight of Madonna whipping off her shirt to change into another outfit. Nothing modest about this girl, I thought to myself. “That’s something very few people will ever see.” Little did I know that Melissa was there with the costumes. Herb didn’t seem interested. All day long he put the two of them through pose after pose, none of which had anything to do with the movie.

Rosanna and Madonna had a peculiar relationship. On one hand they were friends and even hung out together outside of work, but on the other. . .Madonna had a way of sucking all the air out of the room. It’s my understanding that the movie was greenlit because Rosanna, red-hot after “The Executioner’s Song” and Baby It’s You, had agreed to be in it. Rosanna was unquestionably the lead and worked practically every day, while Madonna’s role was much smaller in terms of actual scenes. But there was no denying that Madonna was Madonna, and she was “Susan” in a movie called Desperately Seeking Susan. Once, when somebody on the street asked who was in the film, I heard Rosanna say “Madonna.”

The truth was, Madonna had the kind of brash confidence that could overwhelm a lot of people, and certainly a more sensitive type like Rosanna. This photo shoot was a perfect example.

At one point, Ritts was shooting some sultry glamour shots of Rosanna posing against a cloth backdrop when Madonna came over. After gaping at Rosanna for a minute she said “You look so good I’d like to fuck you myself.” It was funny, but you could almost hear the air—sssssss!—slipping out of Rosanna’s confidence. Her moment was stolen, and it became all about Madonna. And come on! This was Rosanna Arquette, after all—a true fantasy figure for a good portion of the men in America! Moments later, Madonna grabbed the backdrop, commandeered the same pose… and Herb shot an image that became a famous poster.

Eventually it was time for lunch, so Melissa and I went out and got some sandwiches. That was catering. “Who wants the tuna?” Madonna played me the track “Sidewalk Talk” from the compilation album “Jellybean Rocks the House” that her boyfriend Jellybean Benitez was producing. She seemed pleased that I liked it, which made me feel good. She often made fun of me on the set, but the truth was that I spent a lot of time with her alone, going over pictures in her trailer and in her loft (she lived a few blocks from me), and we got along very well. Her instincts for publicity were amazing even then, and I have always considered her one of my mentors. I’ve learned a thing or two from other publicists, but the best training comes from natural-born salesmen like her. My favorite story about Madonna involves how she got her manager. She asked who handled Michael Jackson, and when she found out it was Freddy DeMann, she called him. Who would have the chutzpah to do that? Freddy signed her.

Legendary style-setter André Leon Talley turned up unannounced and asked Herb to shoot a photo of Madonna for “Vanity Fair”. Before I could say anything, Talley put a pair of multi-colored men’s boxer shorts on top of Madonna’s head and started twisting them around.

This put me in a tough spot because neither DeMann nor Madonna’s publicist Liz Rosenberg had approved this. Madonna said I should call Freddy at home and if he said it was okay, she’d do it. As bratty as she could be, in the important ways she was pretty easy to deal with in those days. I’d say “Look, you have to do this now so that you won’t have to do it later,” and she got it.

It was starting to get pretty late and I decided it was time to put my foot down. I told Herb it was time to shoot the Desperately Seeking Susan costumes. After a very long day shooting pictures completely unrelated to the movie, I think he spent an hour or two doing it.  But those few frames turned out to be gold.

As we were getting ready to go, I saw something that I think very few people have ever seen, at least for a long time. Madonna called Jellybean, and they were in the middle of some kind of argument. For a few moments I saw her impregnable shell break away: She appeared to be a normal young woman unsatisfied or hurt by whatever her boyfriend up to. As I had learned that day, showing her breasts wasn’t a big issue to Madonna, but showing vulnerability definitely was. As soon as she spied me looking, she tucked that honest emotion back into wherever she kept them and became “Madonna” again.

Early the next week Herb turned up at Madonna’s trailer with several hundred dollars worth of extraordinary photos. Platinum Prints. Museum-quality stuff. I’d never seen anything like it. I surmised that he was hoping to photograph Ms. Ciccone again. I think it’s an understatement to say that’s exactly what happened. He became one of Lady Madonna’s top court photographers, shooting many of her most memorable images, until his untimely death in 2002.

Sometime after the film wrapped, I happened to be at the New York Orion office for a publicity meeting when the ad agency was making a presentation. The focus was on the New Jersey housewife part of the movie. Rosanna’s face was on a toaster and Madonna’s face was on a piece of toast. Something I can’t remember with a microwave oven. Each one was more terrible than the one before. As it happened, I had brought a set of the slides from the Ritts photo session to the meeting. I pulled them out and said, “have you guys seen these?” They hadn’t. Ann Lander had gone on vacation and locked the photos up in her safe. Seriously. There was a hush in the room.

This wasn’t the end of the story, though. Some people at Orion thought that the image would make people think it was a lesbian movie. Thankfully the film’s producers, Midge Sanford and Sarah Pillsbury, were able to make their case and the result is the iconic Desperately Seeking Susan poster.

Pretty much every Desperately Seeking Susan slide Herb took during that hour got used thousands of times. One of them even became a “Playboy” cover.

Years later I visited the London Film Museum. . . and there it was! My poster! I was truly proud. I felt that in a tiny way, I had been part of the history of film. After all, that image would not exist if I hadn’t thought it up! Okay, okay, Herb, Rosanna, Madonna, Santo, Melissa, Susan Seidelman, screenwriter Leora Barish and even Ann Lander had something to do with it too.

As Rosanna Arquette is still someone I keep in touch with (and I believe she reads my blog now and then), I apologize for once again making this story all about Madonna. She has always had a way of making everything about her.

Years later I ran into Madonna at Lee’s Art Shop on 57th Street. I introduced myself and said that I had worked on Desperately Seeking Susan. “A lot of people worked on Desperately Seeking Susan,” she said as she walked past me.

Reid Rosefelt is a veteran film publicist based in New York City. He has promoted hundreds of films, for such diverse moviemakers as Jim Jarmusch, Pedro Almodóvar, Errol Morris, Ang Lee and Werner Herzog. His personal clients have included The Sundance Institute, IFC and HBO Films, as well as Harvey Keitel, Ally Sheedy and the late Adrienne Shelly. His production publicity credits include Desperately Seeking Susan, The Godfather: Part III and, most recently, Precious: Based on the Novel ‘Push’ by Sapphire. His blog can be found at http://my-life-as-a-blog.com/