Meeting Sean Penn

Perhaps one of Madonna’s most popular videos is the one she filmed for “Material Girl,” a modern-day reworking of Marilyn Monroe’s most famous vocal performance, “Diamonds Are a Girl’s Best Friend.” Madonna said at the time, “Marilyn was made into something not human in a way, and I can relate to that. Her sexuality was something everyone was obsessed with, and that I can relate to. And there were certain things about her vulnerability that I’m curious about and attracted to.”

When the time came to film the video (two days in Los Angeles in February 1985), Madonna decided on a clear and obvious homage to her blonde inspiration, Monroe. The video featured Madonna wearing an exact replica of Marilyn’s shocking pink gown from the film Gentlemen Prefer Blondes (she hated the dress, however, complaining that it constantly slipped down her bosom), singing on a reconstruction of the film’s set, complete with staircase, chandeliers and bevy of tuxedo-clad chorus boys. (“I can’t completely disdain the song and video, because they certainly were important to my career,” she said later. “But talk about the media hanging on to a phrase and misinterpreting the damn thing as well. I didn’t write that song, you know, and the video was all about how the girl rejected diamonds and money. But God forbid irony should be understood. So when I’m ninety, I’ll still be the Material Girl. I guess it’s not so bad. Lana Turner was the Sweater Girl until the day she died.”)

Freddy DeMann’s assistant Melinda Cooper drove Madonna to the sound stage where “Material Girl” was to be filmed. A photograph taken that day shows Madonna wearing a pink bodysuit and a black velvet shirt, unbuttoned enough so as to reveal her black Chantelle bra. She also wore large dark sunglasses and a wide-brimmed red hat, lest she be recognized.

Because of the enormity of the video production — and the Marilyn Monroe association that was bound to cause a sensation — Melinda Cooper sensed that Madonna’s life and career were about to be transformed. It was an exciting notion. “Do you realize how much things are going to change for you now?” she asked her as they drove to the set.

“What do you mean?” Madonna responded. She had her compact mirror out and was inspecting a pimple. “Jesus Christ. Of all the days to get a zit,” she said, preoccupied. “I ask you, can anything else go wrong in my fucking life?”

“I mean, your whole world is going to change after this video,” said Cooper, ignoring Madonna’s rhetorical question. “Do you know that?”

Madonna snapped the compact shut. “I know that, Melinda,” she said, perturbed. “Now can we please just get there!”

On that first day on the set, while Madonna was standing at the top of the staircase and waiting for filming to begin, she gazed down and noticed a guy in a leather jacket and dark sunglasses striking what seemed to be a deliberate pose in a corner, looking back up at her intently. He was twenty-four-year-old actor Sean Penn — born on August 17, 1960 — at the time considered the most moody and brooding (and probably most talented) of the young Hollywood actors who made up what was known as “the Brat Pack.” (Others in the so-called Pack included young actors Charlie Sheen and Emilio Estevez.) Because he hailed from a privileged background, having been raised in Beverly Hills with both parents in show business (his father is television director Leo Penn, his mother actress Eileen Ryan), Penn didn’t have to struggle much to break into the business. However, his privileged lifestyle didn’t make him any less angry. He had a reputation for being an intensely private, sometimes violent and extremely jealous young man — and he was also thought of as a proficient actor thanks to roles in Fast Times at Ridgemont High, Racing with the Moon and The Falcon and the Snow Man. After having expressed an interest in meeting Madonna, Sean Penn had been brought to the set of “Material Girl” by the video’s director, Mary Lambert.

“He was somebody whose work I’d admired,” Madonna has said, “and I think he felt the same way about me. I never thought in a million years I would meet him.”

As soon as Madonna, still at the top of the stairs and waiting to start her descent, realized that the stranger below was Sean Penn, her heart skipped a beat. Though she fancied actor Keith Carradine at this time (who appeared in the video and with whom she was seen making out in between takes), she knew that she had to meet Penn. Even at first glance, he seemed self-confident and cocky — just her type. When they finally did meet at the bottom of the stairs, he didn’t disappoint.

“Well, just look at you,” Sean Penn said to her as he motioned to the gown and wig. Full of swagger, he hooked his thumbs in the belt loops of his jeans. “You think you’re Marilyn Monroe, don’t you?” He was joking, but Madonna didn’t appreciate his brand of humor.

“What’s the matter with you?” she asked, annoyed. “You don’t even say hello? You just go straight for the insult? Is that what you do? You don’t even say, ‘It’s nice to meet you?’

“Oh, I’m sorry, Marilyn,” Sean Penn said, his voice dripping with phony sarcasm. Sean’s eyes were a bit glazed, a cigarette dangled from his mouth. He extended his hand to shake hers. “It’s nice to meet you,” he said with a warm smile.

Madonna had to laugh. She took his hand and, putting on a whispery Marilyn Monroe voice, cooed, “Nice to meet you, too . . .”

Later, she recalled, “I had this fantasy that we were going to meet, fall in love and get married. Suddenly it’s what I was wishing would happen. Why I fell for him that day, I can’t say. I have no idea. I just know I wanted him.”