When production began on Warren Beatty’s new film Dick Tracy in February 1989, it seemed inevitable to some Hollywood observers that a romantic relationship had developed between the longtime Hollywood rogue and pop music’s current, publicity-mad temptress. Now that she was working alongside him, Madonna, a longtime movie fan, probably couldn’t resist the idea of a relationship with Beatty, a film icon who cultivated women with astonishing success. Because the final and painful breakup with Sean was still fresh, though, perhaps Madonna felt as she might after having been to the dentist. Inside she was probably numb after such a dreadful ordeal, especially considering the Malibu nightmare. However, on the outside she seemed fine — and she was adamant about keeping up appearances. She told friends that she was determined to move forward with her life and remain as distracted as possible, so as not to focus on Sean, her failed marriage and the catastrophic way it had ended. What better distraction, one might muse, than a relationship with a man who had romanced many of the biggest and most glamorous names of his era, including Natalie Wood, Joan Collins, Julie Christie, Carly Simon, Cher and Barbra Streisand?
While still certainly easy to look at, at fifty-two Warren Beatty’s sex-symbol status in Hollywood had long ago faded. Now, around his still-handsome face was the faint suggestion of discoloration, thin white lines that were nearly concealed by either a tan or maybe even pancake makeup. (Some who got close enough for an inspection would wonder if these marks could have been the result of cosmetic surgery.) Perhaps realizing that his “Old Hollywood” image would be bolstered by becoming linked with the young, leading sex object of the day, Warren seemed dumbfounded by his good fortune. “Sometimes I look at myself in the mirror and say, ‘Man, I am with Madonna!’” he told a reporter. “She makes me young.”
From the beginning, Warren provided loads of fun for Madonna. For instance, one day Madonna came home to find her living room full of packages: lingerie, perfume, makeup, and dozens of expensive dresses, both formal and informal — all her size. There were also boxes of bikini underwear in a variety of colors — again, all her size — and a dozen black lace Lejaby brassieres — her favorite. (One might wonder how Warren would have known, or even remembered, the brand name of her favorite bra.) There were also eight pairs of expensive Italian designer shoes. She was astonished when she read a card that had been propped on a large hatbox: “From Warren.” Had he really selected all of these clothes just for her? Had he spent that much time making certain of the sizes? And why would he do all of this?
As she pondered those questions — and who knows how many others — Madonna and two of her female assistants enjoyed a wonderful afternoon with Warren’s exquisite presents. After putting her Like a Prayer CD into the player, she slipped in and out of each new dress while dancing and preening in front of the mirror, admiring her reflection. She and her friends enjoyed “a silly girl’s day,” as one of the assistants called it. They pinned up their hair, let it back down, sampled the new lingerie — tags dangling — and tossed aside the garments Madonna decided were “tacky.” At the end of the fun day, Madonna gave the two girls the clothing and makeup she thought flattering on them, and kept the rest for herself — including all of the shoes.
The next day, Madonna telephoned Warren to ask about the gifts. He explained that buying for himself was a bore since, as he put it, “a man can only wear pants and a jacket. What fun is that?” He said that he enjoyed shopping for women and, if Madonna didn’t mind, he might send over an assortment of “goodies” whenever the mood struck him.
Madonna was ambivalent about such generosity. As she would later say, she was, at first, annoyed. “I’m not some little starlet that you can buy things for and control,” she told him. “I’m a very wealthy person. I can buy my own underwear.” However, she was also impressed. “What girl wouldn’t be?” she had to admit. After what she had been through with Sean, perhaps she decided that she deserved a bit of pampering. She decided to keep the gifts, but on the condition that the next time Warren Beatty had such an impulse, he would take her along so that she could help select “the goodies.”
As well as his passion for beautiful and famous women — and for buying them “goodies” — Warren Beatty’s other great love was of filmmaking. On Dick Tracy, he would act as star, producer and director. Madonna could learn a great deal about moviemaking and screen acting from him. She needed his credibility and experience as much as he needed her youth. To her restless child, he would play the indulgent adult, slightly abashed but definitely enchanted by her whirlwind lifestyle. Some people in her circle went so far as to say that Madonna looked to Warren as a father figure.
After Sean Penn, Warren Beatty must have seemed like a breath of fresh air for Madonna. For one thing, he could be pushed around — as she would soon learn. He would take a lot, get angry, and then disappear . . . to cool off. Unlike Sean, he wouldn’t lash out at her, at least not in any physical way. It had always been Madonna’s nature to bully the man with whom she was romantically involved. Whereas Sean had been emotional and explosive about her daily defiances, Warren would usually just be resigned and philosophical about them. For the most part, he was tolerant of her; he thought she was amusing.
Ironically, it had been Sean Penn who first introduced Madonna to Warren Beatty, and on the night of Penn’s first date with her, “Sean took me to Warren’s house,” Madonna said. “I guess he wanted to show me off — I’m not sure. I didn’t know L.A. at all. I remember meeting a lot of movie stars that night, like Mickey Rourke.”
Warren was intrigued by Madonna from the first time he laid eyes on her. “I understand rebellion,” he observed when speaking of his new consort. “So I understand Madonna. She’s all about rebellion, basically.” (If that’s all she was “about” in his view, maybe he didn’t understand her as well as he thought he did.) To Vanity Fair writer Kevin Sessums, though, Warren was a bit more forthcoming when asked what he thought of Madonna’s artistry: “I think she’s courageous in the areas that she explores artistically. I think that’s what she wants to explore. If you mean what do I think are the resonances of that or the personal motivations for that, I don’t know that I would address myself to that. Off the top of my head, her generous spirit would be the thing I think that informs her work the most. As she goes on, she will gain the artistic respect that she already deserves.”
Diane Giordano recalled the way Madonna described a date with Warren at the Sushi Cove, a trendy restaurant in Los Angeles on Mullholland Drive, less than a mile from Warren’s estate, in January 1989: “He wore a black silk suit, black shoes, a white shirt and a black silk tie. He also wore tinted glasses. She suspected that he was trying to hide crow’s-feet. She said she felt awkward because he was so nattily dressed and she had on a funky jeans outfit. They had a nice dinner and then the waitress came and asked if they wanted dessert. The only choice was chocolate or vanilla ice cream. Madonna wanted both.”
The next day, Warren telephoned Madonna at her home. In talking about the date, he went on about how Madonna had wanted both flavors of ice cream. “You seem to like to try everything,” he told her, teasing her. “So, have you ever made it with a woman?”
At this time, with Madonna’s friendship with Sandra Bernhard flourishing, she was still teasing the public with the possibility that she was a lesbian. With Beatty now apparently questioning the validity of “those stories,” Madonna suddenly became the model of discretion. She refused to answer his inquiries and, instead, attempted to turn the tables. “Have you ever done it with a man?” she countered. Beatty, it is said, ignored the question.
“Do you want a woman?” he pressed on. “Because if you do, it will be my present to you. I’ll get you a woman.”
“And all this, just from ordering two kinds of ice cream?” Madonna asked with a laugh.
The next night, Warren and Madonna — in a black vinyl jumpsuit with high heels (strange fashion choice for beach restaurant dining) — again dined at the Sushi Cove, this time joined by Sandra Bernhard, at Warren’s request. “All I remember about that date was that Madonna and I ordered one plate of sushi for the two of us. And I said something like, ‘Warren, you know that Madonna and I share everything, don’t you?’ And his eyes lit up like a kid in a candy store. A wild ride, I thought to myself. A very wild ride.”