While researching his new biography Madonna in Manhattan last winter, Andrew Morton encountered a fan whose feelings for the 43-year-old pop icon went well beyond star worship. “She told me, ‘Whenever I have a problem, I think, what would Madonna do?’ ” recalls Morton. “I thought, people don’t say, ‘What would Cher do or Michael Jackson do?’ Madonna is a role model.”
Judging from Morton’s book, excerpted exclusively below, fans might think twice before following her lead—at least when it comes to love. Morton, who interviewed more than 70 of the star’s associates, friends and relatives over a seven-month period, portrays her as an insecure manipulator so desperate for affection that she scared off some boyfriends, two-timed most of them and almost always made foolish choices. “Many of the men in her life have been arm candy,” says Morton. “She flirted with Michael Jackson and had a relationship with Warren Beatty, but many of the others, like Carlos Leon and Jim Albright, were not well known. She spent a long time looking for love in all the wrong places.”
Not that the London-based Morton, 47, author of Diana: Her True Story and Monica’s Story (about Monica Lewinsky), found his latest subject unsympathetic. “We have this image of a hard-boiled, sassy New Yorker,” he says. “But she is more of a decent person than that.” As for her checkered romantic experiences, he adds, “she has wanted to give love, but when she receives it, she rejects it.” Whether or not her second husband, English director Guy Ritchie, 33, can break the pattern remains to be seen. Says Morton: “Her life has been a quest for love.”
The quest began after Madonna‘s adored mother and namesake died of breast cancer at age 30 in 1963, when her eldest daughter was 5. Shattered, little Madonna Louise began competing with her five siblings for the attention of their father, Tony Ciccone, now 70, a retired defense engineer. Getting noticed got harder in 1966, the year Ciccone married the family’s housekeeper, Joan Gustafson, now 58, who eventually had two children with him. “Miss Goody Two Shoes,” as Madonna has described her pre-Joan self, started acting out soon after the family moved from Pontiac, Mich., to the more upscale Rochester, also in Michigan. In rebellion against her strict Catholic dad and resentful of her stepmother (to whom she is still not close), 14-year-old Madonna took up smoking, wore tight clothes and slathered on makeup. Boys—lots of them—became her priority. At 15, Morton writes, she had her first serious sexual experience, going “all the way” with her boyfriend at his parents’ house.
Madonna sought attention in more productive ways as well, setting her sights on a career as a professional dancer. She landed a dance scholarship to the University of Michigan in 1976 but left after two years to seek fame in New York City. Getting by on what she earned at menial jobs—including hat-check girl and the occasional gig as a nude artist’s model—she lived in a series of decrepit apartments while dancing with the respected Pearl Lang company. But Manhattan had its perils. In the fall of 1978 Madonna was sexually assaulted at knifepoint on a tenement rooftop. Morton writes that the experience “undoubtedly increased her sense of isolation and loneliness.”
Later that year Madonna, who had sung only in occasional high school productions, opted out of the rigors of professional dancing, telling Pearl Lang, “I think I’m going to be a rock star.” Her boyfriend at the time, an aspiring musician named Dan Gilroy, had taught her to play guitar and drums, and in 1979 Gilroy, Madonna and three others formed the short-lived garage band the Breakfast Club. But by 1983 it was Madonna the solo act, then 24, that was going places, with two hit dance singles, “Everybody” and “Burning Up,” under her belt. A fixture on the downtown club scene, she met John “Jellybean” Benitez, a deejay and aspiring record producer, in late 1982. Benitez, then 25, produced “Holiday,” one of the hits from her debut album, Madonna. Soon they were mixing work with play.
After weeks of flirting, Madonna and Jellybean began to be seen together regularly [in early 1983], arriving as a couple at the trendiest venues around Manhattan. Many expected that Madonna and Benitez would marry, especially when they became engaged and began living together in Soho. “He was in love with her,” observes his friend Arthur Baker. “They were a great team. But she was the one in charge. She’s a diva—man, they like to command attention.”
Jellybean, too, liked to command attention. “He’s a Scorpio and we both want to be stars,” Madonna admitted at the time. These limitations were further exposed when Benitez discovered that, behind his back, Madonna was seeing Steve Neumann, a journalist who was in a relationship with Madonna‘s friend Erika Belle. While it was a short-lived fling, her behavior did little to cement mutual trust.
[In early 1985], Madonna discovered that she was pregnant by Benitez. [It] came as a shock. After discussing matters with her lover, Madonna decided it would be best if the pregnancy were terminated. Her manager, Freddy DeMann, was on hand to make the arrangements. As Melinda Cooper, DeMann’s assistant, told [Madonna], Unauthorized author”] Christopher Andersen, “She was very upset—just this scared young girl who didn’t want her family to know.”
Benitez escorted Madonna to the American Music Awards in L.A. the next month—only for Madonna to lose the title of Favorite Female Pop Vocalist to Cyndi Lauper. It was to be their last date, although Madonna remained on good terms with Jellybean.
Her hit album Madonna had made her a household name, but 1984’s Like a Virgin transformed her into a formidable force. Suddenly Madonna wannabes were everywhere: She had the fame she had always craved—and before long she found the boyfriend to go with it.
Her fateful first meeting with the man who would become her husband had actually taken place just as the relationship with Benitez was ending. Legend has it that, as she stood waiting to descend the staircase on the  set of her “Material Girl” video, Madonna looked down and saw the man she would marry. Director Mary Lambert had invited her friend Sean Penn along to watch the shoot. Hard-drinking, violent and abusive, if immensely talented, Penn [then 24] was a member of the so-called “Brat Pack” of young Hollywood actors. Madonna noticed Penn hovering off-set. At that moment, she later claimed, she “had this fantasy that we were going to meet and fall in love and get married.”
[In June 1985], after spending only a few weeks together as a couple, Penn asked Madonna to marry him. He popped the question one Sunday morning in Nashville, as his bride-to-be bounced naked on their hotel bed. At the time rumors were already rife that Madonna was pregnant. Years later, Madonna confided to friends that she had indeed been pregnant and had had a second abortion that year.
“The abortion was traumatic for both of them,” notes a friend. Indeed, it can be argued that the issue of children was to be one of the main stumbling blocks in the marriage. Years later, Madonna admitted, “Sean wanted to have a child. It wasn’t the right time.”
With the announcement of her engagement, the media went crazy. Penn had already got on the wrong side of the press when, while in Nashville, he had attacked two journalists with a rock. He was charged with assault and battery and received a short suspended sentence and a fine.
The couple had decided to marry on her birthday, Aug. 16, at a secret location in California. Madonna themed the wedding around the tale of Cinderella. Gold slippers formed the centerpiece for each table, and her wedding dress designer, Marlene Stewart, was instructed to create a ’50s-style concoction fit for a princess, such as “Grace Kelly would have worn.”
The couple went to elaborate lengths to keep the media at bay. Yet despite these precautions, Madonna‘s fairytale wedding, held outside the Malibu home of the millionaire developer Kurt Unger, degenerated into nightmarish farce. Unger’s cliff-top house was surrounded by photographers, while the noise of low-flying helicopters made it impossible to hear the couple as they took their vows. Indeed, before the ceremony, Penn ran down to the beach and scrawled “F— OFF” in giant letters in the sand and even fired warning shots at the aircraft from a pistol.
Matters were not helped when nightclub owner Steve Rubell vomited into the swimming pool or when the maid of honor, Madonna‘s sister Paula, declared, “This should be my wedding day, not hers. I should be the famous one.” As the couple danced to the strains of Dinah Washington’s rendition of “Mad About the Boy,” many thought “mad” summed up the union.
Madonna‘s marriage was at first a great adventure. Now a Hollywood wife, she was perfectly situated to fulfill her other dream: becoming a movie star. Yet while critics praised her in 1985’s Desperately Seeking Susan, her second film, 1986’s Shanghai Surprise, in which she played a missionary opposite Penn’s hustler salesman, tanked at the box office following harsh reviews. Her marriage was about to tank too.
When Sean failed to visit his wife on set during the filming of Who’s That Girl? [in 1986], it fueled rumors that they were about to split. “The press would make up the most awful things that we had never done, fights that we never had,” Madonna recalls. “That put a lot of strain on our relationship.”
The Penns fought back where they could, Sean often with his fists. One evening in April of 1986, as Sean and Madonna were relaxing at an L.A. nightclub, one of her friends, the songwriter David Wolinski, walked over and kissed her on the cheek. By all accounts, Penn flew into a rage and began beating Wolinski, only stopping when the club’s owner and a visibly shaken Madonna dragged him outside. Penn was fined $1,000 and given a year’s probation.
On May 25, 1987, [Penn] was arrested for speeding and running a red light in L.A. He pleaded no contest to the charges of assault [from two earlier incidents] and reckless driving and was sentenced to 60 days in jail with two years probation. He served 30 days in the Mono County Jail in California. On his release he took a pizza home to Madonna, but, by his own admission, she was not pleased to see him. As he observed: “Going to jail is not good for any marriage.”
Madonna filed for divorce in December 1987, then withdrew the suit. But by mid-1988, she was spending more time with comedian Sandra Bernhard than with her husband.
When Sean returned home from filming in Southeast Asia in June 1988, he discovered that there were three of them in the marriage. Bernhard, , went everywhere with them. When Madonna arrived with Bernhard as her “date” for the opening night party for Penn’s play, Hurlyburly, her husband exploded in fury.
Were Madonna and Bernhard lovers? While they have kept the public guessing, privately Madonna answered in the affirmative when asked. Jim Albright, who enjoyed a stormy three-year relationship with Madonna during the 1990s, believed they had slept together. “I asked her why, because I can’t stand [Sandra]. She didn’t give me an explanation.”
The end of the Penn marriage, when it came, was as dramatic as the beginning. After hours of arguing on the night [of Dec. 29, 1988], Penn grabbed his wife, threw her down and sat on her, pinning her arms to the floor. In spite of her screams and tears, he kept her like that for what she later told friends was about four hours. After a while, her sobbing ceased and she just lay there, utterly traumatized.
“She is never still for a minute, so to do that was like death to her,” says a friend to whom Madonna related the story. “There was a lot of symbolism in it, him wanting to hold her back.” In those few hours, any hope of a reconciliation died. A month later they were divorced.
Divorce didn’t slow Madonna‘s career. Her Like a Prayer album, released in 1989, sold 4 million copies, and that same year she landed a role in Dick Tracy opposite Warren Beatty, who briefly became her lover. She was 33 and at the zenith of her fame when she met Robert Van Winkle, better known as the rapper Vanilla Ice, 24.
In 1991 they didn’t come much bigger than Vanilla Ice. [Madonna] pursued him, intrigued by his success. He didn’t much like her music—”friendly-assed corny s—“—and he was concerned about the difference in their ages. Yet in the end he lost his caution. “We started talking, feeling each other out. Real personal and in-depth conversations.”
As the months passed, however, he began to see a different side of her. “I was digging her,” he says, “but there was a desperate neediness about her, an impatience to get married.” It was [also] clear that Penn was still very much in her heart. “I felt that she still loved him,” says Vanilla Ice. “In fact, I know she did because she told me.”
Their affair was ending when shooting for her racy coffee-table book Sex began. Hired as Madonna‘s bodyguard for the project, Jim Albright, 22, found her “bitchy and demanding,” but he was intrigued. So was she. Their three-year romance, kept secret from the public, began in February 1991.
[Albright] was both alarmed and dumbfounded by the turn events had taken. Here he was, a guy from Hackensack, N.J., falling for one of the world’s biggest sex symbols. “I could feel myself being sucked in,” he remembers. “How far, realistically, was I going to go? It was like I was making a pact with the devil.” On the night before they left for New York [from Miami, during the Sex shoot], she told him she loved him. “That blew me away,” Albright says.
They were soon enjoying a “hot and heavy” affair. He noticed, however, that as soon as he left his longtime girlfriend [Melissa later that year], their relationship changed. It seemed to him that it had been a game for Madonna to encourage him to leave Melissa.
[In 1993], Albright quit working as Madonna‘s bodyguard, taking another [security] position. It proved a change for the better, as Albright recalls: “We just got closer.” She and Albright were on the phone to each other almost constantly. On every day of their three-year relationship she either called or paged him using a secret code. When he could afford it, he bought her tiger lilies, her favorite flowers. When he moved into a bigger apartment in North Bergen she bought him a microwave and a quilt. She was always concerned about his well-being, “like a mother sending her child off to school,” he says.
To Albright [who is of mixed Native American, Afro-Caribbean, Polish and Italian descent], it was clear that Madonna wanted children, especially a child of mixed race. As he says, “She loved my skin color and she was always fascinated by interracial children.” They had even chosen names for the children they planned to have: Lola for a girl and Caesar for a boy.
Yet details seemed to keep getting in the way. There was the thorny issue of a prenuptial agreement. Madonna was adamant that they draw one up, but Albright argued that as he was not, and would never be, financially dependent on her, there was no need. Albright felt, too, a growing sense of distrust not just about the other men in her life but also the women. Virtually everywhere he and Madonna went the slim figure of Ingrid Casares, then 29, the daughter of a millionaire Cuban businessman, would go with them. To Albright, she was a buffer, her presence preventing him and Madonna from growing closer.
At first, Madonna shrugged off accusations from Albright that she and Casares were lovers, saying she was helping [Ingrid] overcome her addictions, both to drugs and to her former lover, Sandra Bernhard. Later, however, she confirmed to him that they were more than just friends.
Over the months, his discovery of her secret friendships with everyone from actors to sports stars sapped his faith in her. As Albright observes, “She’d never been faithful to one man—period. She told me that. She is only loyal to herself.”
As they became increasingly estranged, however, Madonna seemed to become more needy. “She became very, very insecure,” he says. “She was always accusing me of cheating on her.” She left endless messages on his answering machine, their tone by turns humorous, cajoling or desperate.
Finally Albright refused to take her calls, even though she would call him up to 30 times an hour. By the time she arrived in Buenos Aires in October, as part of her Girlie Show tour, Madonna was so distraught that she would no longer perform unless he spoke to her. Still he refused. With the minutes ticking away one night her manager, Freddy DeMann, called Albright and convinced him to speak to the singer. She was hysterical, but after they had spoken she calmed down enough to go through with her show.
The controversy over Sex, condemned as pornographic, and the hate mail it generated, shattered Madonna‘s once-unshakable confidence. But it was her fury when Albright confessed he had had a brief fling himself that spelled the end. They parted ways in January 1994.
In New York six months after her breakup with Albright, Madonna was running in Central Park when she did a double-take as she passed a fellow jogger. She thought it was Albright, or if not, his brother. She asked one of her entourage, Danny Cortese, to find out who the runner was. Cortese discovered that he was a fitness instructor named Carlos Leon. Intrigued, she instructed Cortese to arrange a meeting.
Leon proved himself to be considerate, affectionate and protective. He and Madonna led a quiet life, often walking unnoticed to the cinema or shopping. Inevitably, however, Ingrid Casares would be around, ensconced in Madonna‘s apartment or joining the couple for dinner.
Although he had aspirations to be an actor, Leon found his elevation to instant celebrity hard to take at first. On one occasion he gave the waiting paparazzi the finger, a gesture that earned him a rebuke from Madonna. Still, at her 37th-birthday party in August 1995 Madonna told friends she and Carlos were planning to start a family—but after the filming of Evita, the part she had always longed for.
The discovery during filming [in early 1996] that she was 11 weeks pregnant was greeted as much with guilt as with joy, for she worried that her condition would upset the shooting. Continually nauseous and tired, she was pleased when Leon arrived from New York with a resupply of her favorite candy—red hots.
On October 14, 1996, Madonna, now 38, gave birth to a baby girl at Good Samaritan Hospital in Los Angeles. She named the baby Lourdes Maria Ciccone Leon, but she was known to everyone as Lola. “The whole idea of giving birth and being responsible for another life put me in a different place,” Madonna said shortly afterwards. “My daughter’s birth was like a rebirth for me.”
Once they had time to draw breath, however, it was clear to Madonna and Carlos that their relationship was not working. Carlos, hurt by media gibes that he was simply a sperm donor, felt that she could do more to help his budding acting and modeling career. Madonna felt that he should stand on his own two feet. In May 1997, seven months after Lola’s birth, Carlos and Madonna parted. “It was a real relationship,” says her friend Rosie O’Donnell. “They made a valiant effort to stay together.” Lola remained with her mother, although Carlos, an adoring father, is a regular visitor.
Almost two years after Lourdes’s birth, Madonna attended a party at Lake House, the Wiltshire, England, home of her friends Sting and his wife, Trudie Styler. That evening she met a 29-year-old director named Guy Ritchie.
As Sting’s butler hovered, the talk was of the indie film Styler had part financed and co-produced, Lock, Stock and Two Smoking Barrels, a violent story of gambling, gangsters and stolen ganja. The director sitting next to Madonna and his partner, producer Matthew Vaughn, were looking for a record company to produce and market a soundtrack album. Would [Madonna‘s company] Maverick be interested? The CEO was enthusiastic, and not just about the movie. “I had a whole premonition of my life fast-forward,” she recalls. “My head didn’t just turn, my head spun round on my body. I was taken by his confidence. He was sort of cocky but in a self-aware way.”
Madonna saw in Ritchie the qualities so often ascribed to her. “He’s a risk taker and he’s got a hungry mind,” she noted. And unlike so many of her previous boyfriends, Ritchie had made his own luck. “Guy works almost as hard as Madonna does,” her friend [actor] Rupert Everett remarks. “He’s definitely not a boy toy.”
Still, his stubborn focus on career hindered their developing romance. It was very much an on-off relationship, neither willing to give up their home turf. That Ritchie was involved in a year-long relationship with TV presenter Tania Strecker hardly helped. “He was the love of my life,” says the leggy, six-foot blonde, blaming the singer for her eventual breakup with Ritchie. For while he was seeing Strecker, he was also quietly showing Madonna around London when she was in town. When they were apart, Madonna reverted to characteristic behavior, demanding to know where he had been and who he was seeing. During one dinner with Trudie Styler, Sting and others in New York in late 1999, she was physically restrained from phoning Ritchie by other guests, who suggested that her behavior was likely to drive him away.
As the millennium came to an end, Madonna was the first to give way, agreeing that she should live in London. Soon afterwards, she discovered she was pregnant. There was no question that she would have her baby—Madonna confessed that she had found her “soulmate” in Ritchie. Yet there seemed to be a marked reluctance on his part to commit to a woman 10 years his senior. The fact that Strecker was still in the background complicated things. “I’m not saying the last time we [she and Ritchie] met, because that’s a bit of a sore one—not for me but for her,” Strecker has said. “She is frightened of me.” The implication is clear; he was still seeing Strecker after he had taken up with Madonna. In February 2000, however, Strecker’s relationship with Ritchie petered out.
During her pregnancy, Madonna was diagnosed with placenta previa, a condition that can cut off the baby’s blood supply and greatly increases the risk of hemorrhage for the mother. [That summer], she flew back to L.A. and made arrangements to have a Cesarean once she had gone to term. On the evening of Aug. 10, a month before her due date, Madonna felt unwell and asked a member of her staff to drive her to Cedars-Sinai Hospital. On the way she rang Ritchie [now also in L.A.], who was at a screening of his new movie, Snatch.
By the time he arrived, Madonna was losing blood fast and, according to at least one report, was close to going into shock. With Ritchie holding her hand, she was wheeled into surgery where, at 1 a.m. on Aug. 11, she gave birth to a 5-lb. 9-oz. baby boy, Rocco John Ritchie. Premature, he was placed in an incubator for five days, Madonna taking him to her Los Feliz home in time for her 42nd birthday. To Ritchie, it seemed the right moment to make an honest woman of her. On her return home, Madonna discovered a crumbled paper bag by her bed. She was about to throw it away, “then I noticed something in it, a little box,” she recalls. Inside was a diamond ring and a card. “It was a really sweet letter that he wrote to me about everything we’ve been through, my birthday and the baby and how happy he was.”
Held the day after Rocco’s christening, just before Christmas, the wedding managed to remain completely private. The couple’s choice of the grand but remote Skibo Castle outside the quiet town of Dornoch [Scotland] was about as far removed from Hollywood glamour as it is possible to be. On hand were Sting and Styler (two of Rocco’s godparents), Madonna‘s father and sister Melanie, Ritchie’s parents and a clutch of the couple’s best friends, including Donatella Versace, Ingrid Casares and Gwyneth Paltrow.
“We wanted to find a place that was really hard to get to,” Madonna said afterwards, “because when people have to work hard to get somewhere, you know they really want to be there.”