Sandra Bernhard

During the 1988 run of Speed-the-Plow Madonna had a dream that she and actress/comedienne Sandra Bernhard — a casual friend whom she had met a few years earlier — had survived a catastrophe and were the only two people left on the planet. Madonna had always placed importance on her dreams. She enjoyed sharing with friends the details of her nightly dreams and also recorded them in journals. So, she was astonished when, a few weeks later, she went to see Bernhard’s Off-Broadway play Without You I’m Nothing and heard one of her monologues referring to the comedienne’s fantasy that she and Madonna had survived World War III and were now indeed the last two people on earth.

Madonna had actually first met Warren Beatty and Sandra Bernhard at the same party, at Beatty’s home, both of them introduced to her by Sean Penn. “We met and got to know her when she came to see my show,” Sandra now recalls, “and she really enjoyed it, so she came backstage and we really hit it off. We just started becoming friends, that’s all. Before that, she was someone I just knew through Sean. I was always fascinated by her. When I would see Sean at a party and she was there, she would give me the evil eye, like she thought maybe Sean and I were fucking. But we weren’t.”

In Bernhard’s dressing room after the show, Sandra told her, “I can’t imagine being you.” Unfazed, Madonna — wearing a white Chanel dress that exposed plenty of cleavage — replied, “I can’t imagine being you.” Madonna so enjoyed Bernhard’s act, she even toyed with the idea of playing herself in the movie version of Bernhard’s play (which never happened).

In the five years since Madonna had first come to prominence, she had become accustomed to the fact that she could not be harmed by scandal. In fact, any controversy to which she was attached merely added another layer of intrigue to her infamous image . . . and that usually meant more money in the bank. When one of her backup dancers expressed concern that being involved in a steamy dance scene with Madonna might damage his career, Madonna lectured: “The more notorious you are, the more you’re going to work. Don’t you guys understand that?” She certainly understood it, and exploited it better than any other performer. Now, Madonna may have decided that her friendship with the openly bisexual Bernhard gave her a new act, something else to get her name in the papers and to start Middle America’s tongues a-wagging: lesbianism.

Within weeks of their growing friendship, Madonna was immersed in a lesbian subculture, socializing in New York “girl bars” and showing up dressed in the same gay fashions as her “gal pals.” Bernhard and Madonna added Jennifer Grey to their small band of carousers and, in a take-off of Sean Penn’s “Brat Pack” status, they dubbed themselves the “Snatch Batch.” The gals began an “in your face” promotion of their “lesbian” exploits — leading to gossip that Madonna and Bernhard were having an affair. When asked by reporters, Madonna encouraged the gossip, giggled and blinked and only halfheartedly denied the rumors. A gleeful Bernhard — getting the most publicity of her career so far — played along.

“She is probably one of the world’s sexiest women,” Sandra told a reporter for Penthouse. “She’s worked hard at it and done some interesting things with it. Despite all of the mixed messages people think she gives, she’s one of the smartest women in the business — and most disciplined — and I really admire her. I think what she has done is great, and that makes her sexy to me.”

The witty and talented Bernhard had a reputation for her wild antics and vulgar mouth. When Bernhard was booked on David Letterman’s The Late Show with David Letterman — taped at Manhattan’s NBC studios — Madonna tagged along. Bernhard appeared first and Letterman wasted no time in asking her to “talk about your new good friend Madonna. Is there any truth to this nonsense?”

“A tad,” was Bernhard’s response. “A hair.”

When Letterman asked Bernhard what they did when they went out, she replied, “We party and we get crazy. We drink tequila, we talk about old times, and we get to know each other a little better. What do you think you do with a girlfriend? What do you do when you go out with your girlfriend?”

Then Madonna made a grand entrance, wearing an outfit matching Sandra’s — knee-length jeans, a simple white T-shirt, black shoes with ankle-high white socks. Ever impatient for a media fracas, Madonna wanted to get the ball rolling. “Let’s talk about me and Sandra,” she instructed Letterman.

Letterman, tactfully prying, asked Madonna for her version of what she and Sandra did when they were together, and he wondered if he could be a part of it. “If you get a sex change,” Madonna shot back. Her posture was all masculine, legs spread apart, slouching. There was nothing traditionally feminine about her at all.

“We meet up,” Bernhard interjected, “sometimes with Jennifer Grey, sometimes just the two of us. You usually find us at the Canal Bar or at M.K [two lesbian bars].”

Madonna pushed it farther: “. . . en route to the Cubby . . . ,” leaving Bernhard to finish with “Hole.”

Bernhard whipped the little act to a fever pitch by claiming she had slept with both Sean and Madonna.

While sprawled all over the set’s furniture — practically reclining on it rather than sitting on it, and with their legs wide open — the two spoke over one another, laughed at each other and at Letterman, and were raucous, rude, annoying and unappealing in every way.

“We just thought it would be fun,” Sandra now explains. “She had never done Letterman before, and she was afraid to do it on her own, so I said, ‘Look, come on with me and we’ll fuck with him, and with everyone else.’ It turned out to be a lot crazier than I think either of us expected, though. I really think we were great guests, even though David looked like the whole thing confused him.”

Judging by what she said and did, Madonna didn’t seem concerned about what her husband, Sean Penn, still filming Casualties of War in Thailand, would think of her latest promotional hook as a lesbian. She realized, no doubt, that the international publicity and worldwide attention generated by such a surprising twist only served to benefit her career, which, to some observers, seemed as urgent a concern to her as anything else in her life at this time. The fact was that Madonna had never even been to the Cubby Hole. By this time, though, Madonna was well aware that many of her staunchest supporters were homosexual men, and that even a hint that she herself was gay would only strengthen their loyalty and devotion. Soon, she began appearing in gay-oriented magazines as an activist for gay rights, and was even named in the book The Gay 100 as one of the most influential gay people in history.

According to Madonna the press “failed to get the joke.” Madonna would also claim that she and Bernhard were just “fucking with people’s minds,” though some of her friends insist that at this point in her life Madonna was once again exploring her bisexuality, especially after seeing the odd couple fondling themselves and grinding their bodies together while singing the Sonny and Cher song “I Got You Babe” at a New York benefit. Perhaps she was so unhappy with the way matters had turned out with Sean Penn and John Kennedy that she decided to try something different. Or maybe not. Only she would know — and she has denied it. Because Madonna has been frank about her bisexual nature, one has to assume that if she and Sandra — who is open about her own sexuality — were having a romantic relationship, she would have said as much. After all, she’s talked in the past about some of her other dalliances with members of the same sex.

One of Madonna’s first experiences with a female was with twelve-year-old Moira McPharlin. Madonna was the same age. During a sleepover, she and Moira stripped naked and began to explore each other’s bodies. Madonna says that Moira was the first to show her how to insert a tampon. She said that, prior to Moira’s influence, “I put it in sideways and was walking around paralyzed one day.” Of course, through the years she had many other dalliances with women. “Let me tell you this much,” says Erica Bell, her close friend, “I was fascinated by her long before she kissed me. But once she kissed me, wow! When you’ve been kissed by Madonna, you have definitely been kissed.”

When Penn returned from filming Casualties of War that August, he was not amused at the latest scandal his wife’s actions had generated. He disliked Sandra Bernhard as much as she disliked him, but Madonna managed to placate him enough for the two of them to call a truce and celebrate her thirtieth birthday.

In September, free of her commitment to Speed-the-Plow, Madonna returned to Los Angeles to begin work on her next album, which she hoped would unveil a new maturity in her work. Wanting to be near his wife, Penn accepted a role in the new hit play Hurly Burly, but only if it could open in Los Angeles. Although friends like Sandra Bernhard advised Madonna to leave the emotionally abusive Penn, Madonna confessed, “I still love Sean.” While they both worked on their respective projects, the couple had another shot at making the troubled marriage work: Sean moved back into the home he had shared with Madonna in Malibu. The reconciliation was, however, short-lived.

The author observed the two of them in action backstage at the Westwood Playhouse, where Penn was appearing in Hurly Burly. Madonna showed up with Sandra Bernhard, both women wearing matching black trouser suits with plunging necklines. “Eat your hearts out, ladies,” Madonna said to a couple of female fans who began snapping photographs. “This one’s mine,” she added, motioning to Sandra.

When Sean spotted Sandra, he went into a slow burn. “I see you brought your little girlfriend with you,” he told Madonna.

“Now, Sean, don’t get started,” Madonna said with a smile, trying her best to be sweet to him. “This is your night, after all. Be nice.” She blew a puff of smoke from her cigarette into the air and then struck a pose for one of the camera-wielding fans.

Madonna and Sean never allowed the presence of admirers, photographers, reporters or anyone else to stand in the way of a noisy, marital spat. “If it’s my night, then why’d you bring her with you?” he countered angrily, motioning toward Sandra, who stood in the background glaring at him and sipping a Diet Pepsi. The two eyed each other with disdain. Then, there was a sudden strong smell, suggesting that someone had just broken wind.

“Sean, that’s disgusting,” Madonna said.

“It wasn’t me,” he said, defensively. “It was her,” he added, pointing to a sheepish-looking Sandra.

“You know what your problem is?” Sean continued, turning his anger on Sandra. “You’re a little instigator. You like to start trouble, don’t you? You like to see me pissed off, huh? You like the drama.”

Sandra held up a silencing hand. She said nothing.

“And you never fail to give it to her, or to me, do you, Sean?” Madonna said, glowering at her husband. “Can’t we just have a nice time? Why are you trying to pick a fight with us?”

“What are you talking about? You’re the one who showed up here with your girlfriend,” he said, angrily.

“Oh, forget you, Sean,” Madonna countered, ignoring Sean’s truculence. She took a final drag on her cigarette, threw it to the ground and dug her heel into it. Perhaps she sensed a need for a tactful resolution to the public scene. “Sandra and I are going to Crayons [a bar in Westwood],” she said. “If you want to join us, you’re welcome to do so. If not, then I guess I’ll just see you in the morning.”

As his wife and his nemesis walked away, Sean Penn shook his head negatively and spat on the ground. “Women,” he said, annoyed. “Why couldn’t I have been born gay?”