Divorces of the Decade

From Brad and Jen’s breakup to Jim McGreevey’s shocking announcement to Christie Brinkley’s ugly courtroom drama, The Daily Beast looks back on the decade’s greatest splits.

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Brad Pitt and Jennifer Aniston

Brad and Jen met in the spring of 1998 and were married two years later in Malibu in a lavish wedding that reportedly had 200 guests, 50,000 flowers, a gospel choir, four bands, and fireworks. But five years later, there were fireworks with another woman. Pitt went to make Mr. & Mrs. Smith with Angelina Jolie and the rest is history. The house Pitt and Aniston shared went on the market for $28 million, he and Jolie began adding children their lives, and Aniston became a sobering reminder that sometimes nice girls do finish last. Or at least second.

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Paul McCartney and Heather Mills

Not since Lady Macbeth has one man’s wife been blamed for so much. From the beginning of her courtship with Paul McCartney to the acrimonious end of their marriage in 2005, Heather Mills has been delighting tabloid editors everywhere (except of course for the ones she successfully sued in early 2009) with her political grandstanding for PETA, constant temper tantrums, and alleged feud with her ex-husband’s famous daughter, Stella. The divorce trial was heaven to follow, from Mills’ strange request to represent herself to the time she dumped water on the head of McCartney’s lawyer, Fiona Shackleton. “Mrs. Shackleton said something under her breath so I cleansed and baptized her,” Mills was quoted as saying afterward. “I thought it did her a world of good.” Despite the outburst in court, Mills didn’t do badly in the divorce. She raked in a reported £24 million settlement, even if her reputation took a beating.

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Rudy Giuliani and Donna Hanover

As Mayor of New York, Rudy Giuliani never did anything quietly, so perhaps it was to be expected that his divorce would be cantankerous. Instead of claiming irreconcilable differences (or something generic) Giuliani filed for divorce in 2000 citing “cruel and inhuman treatment” as the reason for the split, which he announced in a press conference that was said to have caught Hanover completely off guard. When his estranged wife responded in a claim of her own, her lawyer Helen Brezinsky said, “If there’s going to be a divorce, let’s have the truth about why—Rudy’s open and notorious adultery.” Giuliani didn’t exactly deny this; within months of their separation, he was squiring his new paramour (and now wife) Judith Nathan all around New York and having her over to Gracie Mansion for parties and other visits. This prompted a visit to court by Hanover, who tried to have Nathan barred from the mayor’s not-so-humble abode. In the end, Giuliani actually moved out of the mayor’s mansion and in with a couple of gay friends. “It’s the craziest thing I’ve ever seen,” said former NYC Mayor Ed Koch, discussing the divorce at the time. “It’s all anyone is talking about.”

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James and Dina Matos McGreevey

In August 2004, New Jersey Governor Jim McGreevey announced that he was resigning from office, after admitting to an extramarital affair with a man on his staff. The most troublesome part of the announcement—in which he declared himself to be a “gay American”—that the staffer (Golan Cipel) had been appointed as New Jersey’s homeland security adviser, despite being vastly under-qualified for the job. The saga went on well past McGreevey’s resignation. McGreevey and his wife Dina Matos divorced, and she wrote a tell-all called Silent Partner, about her years in denial. Later, in court with her ex-husband (arguing over money), Matos charged that the day after she gave birth to the couple’s child, he insisted on introducing the baby to the media. “His entire life had been scripted,” she later told Diane Sawyer. When he announced his resignation, Matos claimed, McGreevey told her to be brave, “like Jackie Kennedy.” She was appalled. “My world had collapsed around me.” McGreevey, meanwhile, is trying to give new meaning to his life by studying to become an Episcopal priest.

AP Photo/Danny Moloshok

Britney Spears and Kevin Federline

When Britney Spears filed for divorce in November 2006 from her husband and former backup dancer Kevin Federline just eight weeks after giving birth to their second son, Jayden James, it was only two years after the couple wed. Spears’ divorce coincided with a steep (and public) decline in the singer’s mental health that included shaving her head completely, attacking a paparazzo’s SUV with an umbrella, and exiting rehabs just days after checking in. Spears eventually lost custody of the kids to Federline in October 2007, though by the following summer, Spears and Federline reached an agreement giving Spears visitation rights. This year, the boys even accompanied her on much of her concert tour.

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Ellen Barkin and Ronald Perelman

The actress and billionaire mogul seemed an unlikely pair when they first married in June 2000. But friends claim it was their similarly hardheaded and temperamental personalities that drew them to each other—and what ultimately split them apart. The two met in 1999 at Vanity Fair's Oscar night afterparty, and Perelman pursued Barkin with fervor. They wed the following year, with Barkin signing a prenup just one day before. Within five years, however, the two were barely on speaking terms and hadn't been intimate for months. Perelman served Barkin with divorce papers a month later, reportedly to pre-empt a clause in their prenup that would entitle her to more cash had they stayed together past their fifth anniversary. Barkin moved out of their Upper East Side townhouse under the watchful eye of armed guards. She reportedly ended up with a divorce settlement around $20 million.

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Jack and Jane Welch

No business world breakup had so much juice as that of Jack and Jane Welch. In 2002, Jack, the former head of General Electric, agreed to be profiled by Suzy Wetlaufer, then the editor of the Harvard Business Review. By the time Wetlaufer returned from her interview with the-married CEO, she was already boasting to colleagues that Welch wanted to spend the holidays with her and her family. As news of the affair spilled out over the next few months, Wetlaufer wound up resigning from the magazine. Still, Wetlaufer appears to have had the last laugh. Welch left his wife and married her, and the two went on to co-write a book in 2005—the aptly titled Winning.

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Whitney Houston and Bobby Brown

If a couple’s marriage is dramatic enough for a hit reality show on Bravo, that’s a pretty good indication it will not take death for them to part. Almost from the time they met at the Soul Train Awards in 1989, Whitney Houston and Bobby Brown had a reputation for drama; she for what she later called “partying” and he for fathering kids out of wedlock. And those were the good times. The two were married in 1992, and 14 tumultuous years later, Houston filed for divorce. During Houston’s 2009 comeback tour, she claimed that Bobby had slapped her several times prior to their divorce, spat on her, and cut her face out of family photographs. (Brown denied many of these allegations.) Houston also talked to Oprah Winfrey about Brown’s infidelity, or as she put it, “tracking dirt into my home.”

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Christie Brinkley and Peter Cook

For two beautiful people, Christie Brinkley and Peter Cook had a divorce that was ugly. Then again, that’s what happens when you discover your husband of 10 years is having an affair with an 18-year-old (when he wasn’t purchasing Internet porn at a reported cost of $3,000 a month). And the two traded barbs in and out of the courtroom, and even returned to court a year after settling their divorce in 2008. Cook accused Brinkley of interfering with parenting time with their two children and demanded she enroll in anger-management courses. Brinkley tried to get a restraining order against Cook, so he couldn't see their children. The marriage ended with Cook walking away with $2.1 million, though Brinkley claimed victory since she was awarded primary custody of their children and got to keep their multimillion-dollar property.

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Madonna and Guy Ritchie

Madonna spent much of 2008 denying that something was amiss with her marriage to filmmaker Guy Ritchie, a rumor that reached fever pitch amid reports of an affair with Yankees slugger Alex Rodriguez. (Madonna has consistently denied ever being involved with A-Rod.) Reportedly, the diva sought advice from her gurus at the Kabbalah center about repairing the marriage to Ritchie, but by October 2008 it was over. The British tabloids ran wild. One rumor was that the couple had not had sex in 18 months; another was that Ritchie reportedly told his friends being with her was like “cuddling up to a piece of gristle.” A few months after the split, the Sun reported that the former Mr. Madonna had taken to referring to his famous ex wife as “It.” As in: “It’s in a bad mood today.” To which her press rep Liz Rosenberg responded, “It hasn’t been in a bad mood since the divorce was finalized.” Still, Madonna did pay handsomely for the collapse of her eight-year marriage. By most accounts, the union ended in settlement that cost well over $50 million. Amazingly, the ever-pragmatic Material Girl is said not to have signed a pre-nup.