From PEOPLE Magazine Click to enlarge
WHEN MADONNA DESCENDED on Miami in the winter of 1992 to shoot her steamy peek-a-book, Sex, locals stared slack-jawed at the sight of their distinguished visitor hitchhiking on busy Alton Road in nothing but a pair of spiky black heels. Her own blue-green eyes, meanwhile, were gazing longingly at a 1928 Italian Renaissance-style mansion, located across Biscayne Bay, that she just had to have. One hitch: It belonged to someone with no intention of selling.

Undeterred, Madonna made a few quick inquiries. The owners had paid $2.15 million for the prime piece of property in 1988; four years later its appraised tax value was $1.5 million. Rather than strike any poses, Madonna sent in her younger brother Christopher with an offer that couldn't be refused: $4.9 million—cash. "It was a very simple transaction," says one of the players involved in the deal. "She wanted the house. She had the money. She got it."

What does the Material Girl's retinue of business advisers say about her extravagant ways? "My manager gets insane about what I spend," Madonna once admitted. Not that the 35-year-old superstar, who grew up lower-middle-class in suburban Detroit, plans to change her financial habits any time soon. "I do what I want," she says, referring to the care and feeding of her $100 million fortune. "I'm the boss."

As rich as she is, Madonna is hardly in a league of her own. According to a PEOPLE survey, a current list of showbiz' wealthiest women would include, in addition to Ms. Ciccone, Oprah Winfrey, Mary Tyler Moore, Liz Taylor, Jane Fonda, Goldie Hawn, Barbra Streisand, Dolly Parton—and producers Marcy Carsey (Roseanne and The Cosby Show) and Linda Bloodworth-Thomason (Designing Women and Evening Shade). One thing that unites these female achievers is that they made their money a rather new-fashioned way: They earned it, and not just by collecting paychecks, but by amassing power as producers, entrepreneurs and savvy self-marketers. There may, in truth, be a few wealthier women in Tinseltown: Candy Spelling, for one. the wife of producer Aaron Spelling (Beverly Hills, 90210), holds claim to a sizable chunk of her husband's estimated $300 million. But those who married, divorced or inherited their way to riches weren't considered in the survey: The traditional Ladies Who Lunch, it turns out, have precious little in common with those who Leverage.

Consider Barbra Streisand, who started her professional life as a painfully self-conscious girl singer; last December, Streisand—now a Woman to Reckon With—used her track record as the top-selling female recording artist of all time to hammer out an unprecedented $60 million record deal with Sony. A few months earlier, Madonna had brought to her contract talks with Time Warner Inc. (the parent company of PEOPLE) her legendary moxie along with a balance sheet that shows she has earned the company half a billion dollars in record sales since 1984. She too walked away with a $60 million contract.

Still, not every wealthy woman chooses to play hardball with the boys in the boardroom. Goldie Hawn, for example, likes to catch her business adversaries off-guard. "They come to the table with her public image in mind," says her business partner Anthea Sylbert. "They think, 'She's so sweet and easy and fun.' And she is—but she's also tough." Indeed, Hawn, 47, is one of the few female stars who have been able to bargain successfully for a percentage of what their films earn—à la Schwarzenegger, Cruise and Stallone—instead of straight salary. And, as a producer, Hawn's haul from just one hit—1980's Private Benjamin—totals more than $10 million.

What do these stars do with such huge sums? Traditionally, that question has been answered by a team of financial experts who, for a substantial fee, plot a celebrity's investments, balance her checkbook, even pay her personal-trainer bill. More and more, though, the wealthy women of Hollywood have been listening to the experts—and then taking their own best counsel. "I always tell my accountants, my managers, my bankers or agents: 'I don't need advice, I need information," Dolly Parton, 47, has said. "I will make my own decisions." Just this past winter, Parton and partners sank $6.5 million into refurbishing Dollywood, a 93-acre amusement park in the Smoky Mountains, not far from her hometown of Locust Ridge, Tenn. "Some people think it's a little arrogant to have something like that with my name on it," she has said. Let them. The eight-year-old park has been a solid success, attracting some 2 million visitors annually—just as Dolly figured when she made her financial commitment. "I'm not out to pretend I'm not out to make as good a living as I can," Parton has said. "I'm a business-minded woman."

So is Streisand—though don't expect her to build a Second-Hand-Rose-a-Coaster in Brooklyn anytime soon. The singer-actress-director has been involved in several privacy-protecting, but potentially risky, real-estate deals involving straw men—unofficial partners to whom one gives properly before receiving it back through a quitclaim. Got that? If not, you might want to ask Marcy Carsey, who along with her expertise in sitcoms also knows a thing or two about real estate. Over the past several years, she has invested $20 million in prime West Los Angeles and Malibu properties. One source of Carsey's wealth: her share of the $1 billion syndication revenues from The Cosby Show.

For women who would rather practice their craft than crunch numbers, a conventional approach to money management seems to work best. One of the most conservative investors among Hollywood's wealthy women, in fact, is an actress-aerobicizer once known for her radical politics. Jane Fonda, 55—who has acquired the bulk of her personal $30-to-$40-million net worth by heading her exercise-video fiefdom, producing such films as Nine to Five and On Golden Pond and investing shrewdly in real estate—has, in recent years, put millions into the stock of blue-chip companies like Procter & Gamble and Exxon. "Jane has gone from funky activist to elegant society matron," says a former associate. Two years after her marriage to Ted Turner (himself worth $1.9 billion), Fonda, this onetime colleague says, is a "lady of leisure, into designer clothes, cosmetic surgery and makeup."

Oprah, on the other hand, is frankly into control. The 39-year-old talk show host—who runs her business empire from behind a leather-topped mahogany desk at the $20 million headquarters of her Harpo Studios in downtown Chicago—relies on only one adviser: her longtime lawyer and partner, Jeffrey Jacobs. Oprah owns her show and controls her money," says Jacobs. "There's no board of directors, no committees. Every final decision is hers." And she has no trouble making executive decisions to spend loads of cash. In 1991, for instance, despite the fact that she already owned an $800,000 condo in Chicago and a 160-acre farm near Michigan City, Ind., she spent a reported $3 million for an 85-acre ranch close to the ski slopes of Telluride, Colo., and bought a nearby $1.3 million log-and-stone cabin for use as a guest house. In August 1990, at an auction of Shaker furniture in New Lebanon, N.Y., she plunked down $220,000 for a two-foot-high pine work counter. And, when one of her producers married, she picked up the entire wedding tab, then sprang for a two-week honeymoon on the French Riviera. "It feels good to be able to do things like that with no strings attached," she said, "just because I can."

Winfrey's whims may sound extravagant, but they actually add up to money well spent. That counter is a rare antique likely to appreciate in value, and the producer whose wedding she paid for is a prized member of the staff she considers her extended family and on whom she relies to put on her syndicated talk show, which pays her company more than $45 million a year. Oprah wouldn't overpay for a house—as Madonna did—just to own it. "She grew up poor [in Kosciusko, Miss.], and she maintains a perspective about the value of money," says Jacobs. "She's not frivolous." Not long ago, Oprah stood in the aisle of a K-mart near her Indiana farm agonizing over whether to buy a $7.95 doormat decorated with cats or one festooned with cows. "She just couldn't decide. Then she realized—she could buy both. We have a joke between us," he says. "She still has both feet on the ground; she just wears better shoes."

Mary Tyler Moore, meanwhile, earned her designer evening pumps by employing a different philosophy. "Control," Moore has admitted, "is something I have always dodged." MTM Enterprises, which she and then husband Grant Tinker cofounded in 1969 to produce her classic sitcom The Mary Tyler Moore Show, went on to produce such hits as The Bob New-hart Show, Hill Street Blues and St. Elsewhere. But all of MTM's post-Mary Tyler Moore success, the actress has said, is strictly thanks to Tinker, whom she divorced after an 18-year marriage in 1981. "It's his company," she said. Her contribution: "My initials." Still, when MTM was sold in 1988 to TVS Entertainment, a British broadcasting company, for $320 million, the silent partner walked away with $113 million in cash and stock. Now 56, Moore—who has been married for nearly 10 years to cardiologist Robert Levine, 38—divides her time between Manhattan and a 29-acre estate in upstate New York. There she maintains a 1920s Tudor-style country home complete with a hot-and-cold-running shower specially made for Dash, her golden retriever, and Dudley, a French hunting dog. In New York City she owns a 14-room duplex apartment overlooking Central Park. In town, Moore takes ballet classes, answers her fan mail and, as chairwoman of the Juvenile Diabetes Foundation (she has been diabetic for some 30 years), devotes herself to fund-raising and education.

Virtually all of Hollywood's richest women are committed to community-service. "The only reason I want money is to give it away," Streisand declared two years ago. Two of her favorite beneficiaries: pediatric AIDS research and the Streisand Chair on Intimacy and Sexuality which she has endowed for $300,000 at the University of Southern California. Winfrey earmarks millions for education, abused children and battered women. When she received a call asking her help in saving the Chicago Academy for the Performing Arts, she hung up and immediately asked Jacobs to give the school $500,000. Producer Linda Bloodworth-Thomason, 46, for five years donated her entire Designing Women salary to the Claudia Company; based in her hometown of Poplar Bluffs, Mo., the foundation provides college scholarships to rural Ozark women.

The role model for all wealthy women, of course, is Liz Taylor—who at 61 manages simultaneously to do more ($40 million raised for AIDS research in the past eight years) and live more lavishly than perhaps any other Hollywood celebrity. Comparison shopping is not among her hobbies. She bought her 10,000-square-foot home in Bel Air on sight, furniture included, for $2 million in 1982 and purchased her $153,000 Aston Martin Lagonda on the spot while shopping for a Rolls. Her famous jewels, including the 69.42-carat Carrier diamond Richard Burton gave her in 1969, have given her much joy, but they have also cost her millions to insure; she would be far wealthier, experts say, if she had sold them years ago and made prudent investments. Yet somehow that's hardly an option. Liz wouldn't be Liz if she chose Treasury bonds over a tiara.

And Madonna wouldn't be the CEO of something called Boy Toy Inc. unless she swung wildly between outrageous cheapness and crazy excess. The same woman who willingly overpaid for a Miami mansion, says her publicist Liz Rosenberg, "goes over her hotel bills with a fine-tooth comb. She says, 'Who had this Evian? I didn't.' " Thus, apparently, it has always been. Barbra Streisand remembers meeting Madonna, back when she was still an obscure pop singer. "We took her out for a Chinese meal," Streisand recalled, "and she orders a whole fish! When I go out with people, I don't order lobster or steak. I think maybe they can't afford it or something." Of course, compared with Streisand, almost everyone is impoverished. The 51-year-old star owns seven homes—five of them on a $12 million, 24-acre Malibu estate—and so many art deco, art nouveau, Victorian and Second Empire antiques that she had to rent space in a Manhattan warehouse to store them. Her nest egg, though—the only money she considers truly hers, she once said—is in the New York City savings account she opened in 1960 when she was a switchboard operator. After decades of stardom, it held just $17,000; still, she said, "If I ever have to escape, I'd take the money out of that account." Her friend David Geffen, the music-industry tycoon, shakes his head over Streisand's fretfulness. "Barbra could easily live in the world of have," he has said, "but she can't help herself; she lives in the world of want."

Of course, there is little security in show business, and the world of want is often just a few mishaps away. Goldie Hawn, for all her bargaining savvy, has had some expensive experiences with men. She went through two costly divorces (paying first husband Gus Trikonis $75,000 in 1976, and, five years later, giving second spouse Bill Hudson possession of their $2 million Malibu home) before meeting current live-in mate Kurt Russell on the set of Swing Shift in 1983. Her most unfortunate investment, however, may have come in 1984, when she sank several million dollars in a convoluted limited-partnership scheme, dealings that put her in a position to be sued, successfully, for an additional $1.3 million.

Fortunately, these financial missteps haven't hampered Hawn's easygoing spontaneity. On her frequent shopping trips, she often leaves her silver Jaguar parked outside her $4 million Pacific Palisades home and hops on a bike instead. Recently she pedaled the three miles to Santa Monica, where a dress in the window of the trendy Moselle boutique caught her eye. "She bought it without even trying it on," recalls the shop's co-owner, Hedda Jason. "Just rolled it up in a ball, packed it in her knapsack and rode off."

For Hollywood's wealthiest women, though, such idyllic moments seem rare. Dolly Parton may say all she wants is enough money to buy "some more cheap wigs and jewelry," and Streisand may claim, "There's simply nothing more that I need." But the reality is, these ladies are a driven lot. For the past five months, Winfrey has not only been juggling her on-air and off-camera duties and working on her autobiography but training daily for last week's 13.1-mile half-marathon in San Diego; 50 lbs. slimmer, she completed it in 2 hours and 16 minutes. Even Madonna, the supposed embodiment of self-indulgence, has had, by her count, only three brief vacations in 10 years. "I never take any time off if I can help it," she has said. Whenever she gets an hour of downtime, she says, she spends it making impossibly long "to do" lists. "I've basically gone wildly out of control," the pop star has admitted—and the only thing she knows for sure, sometimes, is why. "Having money," says Madonna, "is just the best thing in the world."

SHELLEY LEVITT
JOYCE WAGNER and LAURA MEYERS in Los Angeles, LUCHINA FISHER in Chicago, CINDY DAMPIER in Miami, and bureau reports

  • Contributors:
  • Joyce Wagner,
  • Laura Meyers,
  • Luchina Fisher,
  • Cindy Dampier.