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Authors: Andrew Morton

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She closed her tour in Turin, in northern Italy, declaring before 65,000 cheering fans that she was proud to be Italian. While in Italy, she met some of her relations from Pacentro, the village in which her grandfather and grandmother, Gaetano and Michelina Ciccone, had been married. It was hardly a glorious homecoming. Although they were intrigued by her fame, and there was talk of her being made an honorary citizen of Pacentro, it was obvious from comments made at the time by some of her relations that they were scandalized by her appearance and behavior.

As her first world tour it was a resounding success, although by its finish Madonna was declaring that she didn’t want to hear any of her songs again and that she didn’t know whether she’d ever write another one. ‘I returned feeling so burned out and I was convinced I wouldn’t go near music for quite a while,’ she said at the time.

Although the film of
Who’s That Girl?
had disappeared from cinema screens before Madonna played her last concert in the tour, her dreams of movie stardom remained undimmed. Before the end of the year the word was out that she was to star in
Bloodhounds of Broadway
, an art-house film with a formidable cast that included Matt Dillon, Randy Quaid and Jennifer Grey. Sadly, however, its director, Howard Brokner, was taken ill with AIDS during filming and did not live to see the finished movie. This time the movie, based loosely on the stories of Damon Runyon, was not a Madonna vehicle, but neither was it to be a success, reviewers finding it too theatrical and somewhat plodding. Madonna had hoped that in choosing a film with artistic integrity her status as an actress would, by association, be treated more seriously. But the film, which had been shot in New Jersey on a tiny budget, did not go down any better with cinema audiences than it had with reviewers; indeed, when a reel of the movie went missing for two weeks during its New York run, no one even noticed. Nevertheless,
Bloodhounds of Broadway
was one movie for which Madonna did not have to take the blame.

The critical and commercial failure of her latest film, coming as it did after the catastrophic
Shanghai Surprise
and scarcely less disastrous, in the United States at least, than
Who’s That Girl?
do not seem to have caused much soul-searching in Madonna. It may be that she suffers a lack of critical faculty when it comes to judging her own acting performances, something suggested by her almost invariable preference for first takes of her scenes. Certainly, and ironically, the characteristics at the heart of her ambition, her obsessional quest for perfection, her need to be in total control and her reluctance to reveal her vulnerability, were the very qualities that betrayed her in her attempts to be an actress. What was unquestionably true is that Madonna is at her most appealing on those rare occasions when she lets down her guard and reveals her humanity. Her dramatic difficulties in her early films were due as much to her personality as to her actual performances. After
Desperately Seeking Susan
, she instinctively chose characters that she could mold into a likeness of herself, strong women who triumphed by virtue of their wits, their sexuality or their courage, or a combination of these features. Thus, seeing these characters as reflections of herself, she always tried to make them likeable, whether to do so was believable or not; indeed, a decade later it was a trick she would try to pull off when she played Eva Perón, the wife of the Argentine dictator. If this was yet another manifestation of her desire to be loved, one result was that the interaction of, say, Gloria Tatlock, the missionary in
Shanghai Express
, was not so much with other characters in the movie, but with Madonna herself. It is no coincidence that her most successful film after
Desperately Seeking Susan
was
Truth or Dare
(outside the USA, released as
In Bed With Madonna),
the documentary about herself.

While her assault on the heights of Hollywood had not yielded the breakthrough for which she had hoped, still Madonna did not give up her quest for the role that would finally win her praise, and make the world take notice of her as an actress. She decided to devote 1988 to acting, and having released her fourth album in the autumn of 1987, she recorded no music in the following year.

Her willingness to take a chance and her desire to broaden her artistic horizons saw her begin the year by turning to the stage once again. When she heard that the actress Elizabeth Perkins had pulled out of David Mamet’s latest Broadway play,
Speed-the-Plow
, she immediately called the director, Gregory Mosher, with whom she had worked on
Goose and Tom-Tom,
and asked if she could read for the role of Karen. A great admirer of Mamet’s work – she had written to congratulate him on producing ‘stimulating cinema’ when his film
House of Games
was released in 1987 – she was inspired by his latest work.

The play was a three-hander, featuring two high-powered and sexist Hollywood characters, Bobby Gould, a film magnate, and his producer, Charlie Fox, played respectively by stage veterans Joe Mantegna and Ron Silver, and Karen, an outwardly demure temporary secretary whose ultimate vision and strength of character result in a kind of epiphany for the hard-boiled Gould. After winning a $500 bet with Fox that he will be able to get Karen to sleep with him, he is ultimately persuaded by her to change his mind and make a film based on a life-affirming book she has been reading, rather than the sleazy commercial offering of his friend. The appeal of Karen’s character for Madonna was obvious. ‘She is a sympathetic, misunderstood heroine who speaks the truth at any risk.’ (Her manager, Freddy DeMann, was not so impressed, moaning that her $1,200-a-week pay wouldn’t even keep him in cigars.)

When she won the role in the face of intense competition from thirty other actresses, she went into six weeks of rigorous rehearsals, only ever complaining, typically, when Mosher ended rehearsals early one day. Ever the professional, she learned her lines assiduously, was always on time, thoughtfully sent flowers to everyone involved with the production before it opened on Broadway in May. Yet, once again, it was not her attitude that ultimately caused difficulties, but her artistic interpretation.

The problem came when, a few days into the read-through, Madonna realized that the character she was to play was not quite the angel of mercy she had initially envisaged. As far as Mamet and Mosher were concerned, Karen’s nature was more ambiguous, both writer and director seeing her as a cunning schemer as much as an innocent idealist. ‘Everybody else saw me as a vixen, a dark, evil spirit,’ Madonna lamented. ‘That didn’t dawn on me till halfway through rehearsal, when David kept changing my lines to make me more and more a bitch, a ruthless, conniving little witch. So in the middle of this process I was devastated that my idea of the character wasn’t what she was at all. That was a really upsetting experience.’

Given that she was playing the pivotal role in the drama, it was in fact Madonna’s job to keep the audience guessing, using her character’s femininity to explore the different ways men and women disguise raw ambition, the former more obvious and direct, the latter subtle and sly. She did not see it that way, however, ungraciously complaining in
Cosmopolitan
magazine that: ‘It was devastating to do that night after night. I saw her as an angel, an innocent. They wanted her to be a cunt.’ Thus she saw the role wholly in terms of herself, going home each night in a miserable mood because her character failed in the context of the play, and sometimes walking offstage in tears.

The critics noticed her similarity to Judy Holliday, but yet again complained that she lacked experience. ‘There is genuine reticent charm here but it is not yet ready to light the lamps of Broadway,’ noted the
New York Post
, while the headline in the
Post’s
tabloid rival, the
New York Daily News
, yelled: ‘No, SHE CAN’T ACT.’ This time Madonna blamed David Mamet, griping that the Pulitzer Prize-winning playwright was ‘not interested in collaborating. I think he’s interested in fascism,’ although that did not prevent the play from breaking Broadway records for advance ticket sales for a serious work.

For a star so utterly convinced of her innate talent, and who had been so successful in so many artistic endeavors, to trip continually on the slopes of theater and film during her relentless ascent to stardom was both perplexing and galling. After all, she had undoubtedly mastered the art of the three-minute video, the compressed drama encapsulated in her performances of songs like ‘Papa Don’t Preach,’ undeniable in their social impact and artistic quality. Of this conflict between her acting on her videos and her stage and screen performances, Michael Musto,
Village Voice
columnist and Madonna camp follower, observes: ‘She has the perfect talent for the highly visual, snappy video format. When it comes down to inhabiting a character in film and interacting with other characters she is usually extremely self-conscious. She is too aware of the camera and trying to look good. Too aware of herself. Unlike Cher and Courtney Love, she fails to radiate natural screen magnetism.’

Whatever her feelings about her acting, by the time her run in
Speed-the-Plow
ended in September 1988, Madonna had reached a pinnacle in her career. By any standards, hers was a remarkable artistic achievement. Just turned thirty, she had appeared in four Hollywood movies, and a Broadway play, while her music had resulted in twelve hit singles and four hit albums. She had also masterminded two sell-out concert tours, the first around America, the second taking in Japan and Europe, as well as the USA; both helping to establish her as a national and international superstar. These were only the outward manifestations of her impact, however. Her courageous and indomitable persona had truly revolutionized feminist politics, offering millions of women around the world the sense that they could be strong, sensual, in control, and yet retain their essential femininity, their gender no barrier to achievement. At the same time, her crusade for AIDS awareness and her empathy with the gay and black communities had shaken gender and race relations. It is little wonder, therefore, that she constantly featured in magazine lists, along with President Reagan and the Russian Prime Minister Mikhail Gorbachev, as one of the top twenty individuals who had shaped the decade. At the end of 1987, she had also been cited in
Forbes
magazine as seventh in a list of top-earning showbusiness personalities, with a gross annual income of $26 million. This made her the top-earning female in entertainment.

Apart from her disappointment over her acting engagements, Madonna had made it to the very top in just five years. Sadly, though, while she was willing to go on fighting for a movie career, she had given up on fighting to save her marriage. By mid-1987 she had accepted that she could no more bend Sean to her will than she could bow to his, and she finally lost interest in the role of Mrs Penn. Proud, strong-willed and competitive, Sean had wanted Madonna to play the part of a domesticated goddess, a woman prepared to slow down her career as they started a family. A star in his own right, he also came to resent bitterly being dubbed ‘Mr Madonna’ as his wife’s career reached new heights. As he pithily observed of his marriage, ‘At twenty-four I didn’t realize the difference between a great first-time date and a lifetime commitment.’

As far as Madonna was concerned, she could be forgiven for thinking that marrying one of Hollywood’s leading actors would further, rather than tether, her career. Stubborn and headstrong, she was unwilling to compromise her commitment to her work, even if that meant alienating her husband. As a close friend explained: ‘While she is definitely into bad boys he was more than she could handle. He made the fatal mistake of trying to put himself in front of her career at a time when it was about to explode.’

Ultimately, she wanted a relationship based on a complex dynamic in which she never gave up control, either of her career or herself, and yet maintained the illusion of being controlled by her husband. In the event, however, she found herself with a man who was out of control in private as well as in public, and yet who wanted to restrict her. In short, she tried to tame Penn, and he tried to domesticate her. It proved to be a recipe for emotional trauma and, ultimately, divorce. ‘We were two fires rubbing up against each other. It’s exciting and difficult,’ Madonna later observed. The last comment was nothing if not an understatement.

Like her former lover Ken Compton, Sean Penn possessed the ability to get under her skin, driving her wild with anxiety and uncertainty. They had made a pact to call each other every day at a certain time no matter where they were in the world. When she was away she religiously called him first thing in the morning and last thing at night, not just to keep in touch but to make sure he was where he said he would be, and on his own. More often than not she could not reach him, endlessly reduced to leaving frustrated messages on his answering machine. ‘I’ve got big phone bills,’ she joked.

Madonna’s insecurity and her husband’s heavy drinking, wild behavior and alleged womanizing combined to create an atmosphere of mutual distrust and anxiety. It was an insupportable situation, and one in which, eventually, something must give. At last, just ten weeks after Penn was released from jail in September 1987, Madonna had had enough. On December 4, she filed for divorce, instructing her attorney that she wanted to revert to her maiden name and invoking the pre-nuptial agreement under which their earnings were treated separately. There was a poignant symmetry to the moment she chose to serve papers on her husband, for she was losing the man she loved at the same time as she reflected on the anniversary of the death of the mother she had lost, so many years earlier. Such poignancy was wasted on Penn, who characteristically went off on a drinking bender with his Hollywood cronies.

For Madonna, as was by now almost a romantic reflex, there was always another man waiting in the wings to keep her company. As one of her former lovers noted, she had become the mistress of the ‘soft landing,’ invariably making sure that she had another place to go, another shoulder to cry on, another rung of the social ladder beneath her foot. That December, if she was ruefully contemplating the end of her marriage, she was also quietly considering her elevation from Hollywood celebrity to American royalty. Ever since her 1985 hit single, ‘Material Girl,’ Madonna’s name had become synonymous with that of Marilyn Monroe, a sex symbol of the eighties paying homage to the blonde bombshell of the fifties who wowed a nation and wooed a president, John F. Kennedy. The difference between these two icons, however, was that Madonna’s ethos was remorselessly life-affirming whereas Monroe’s was vulnerable and self-destructive, drawn to the fall. Nevertheless, when word got out that Madonna had secretly been dating the late President’s son, John F. Kennedy, Jr, in New York in the weeks before Christmas 1987, the symbolism was as uncanny as it was obvious.

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