10 Best & Worst Breakups Ever

The Best Breakups
Let these serve as examples of how mature and loving former partners can be even after the union ends.

Bruce Willis and Demi Moore
When Bruce Willis and Demi Moore got hitched in Vegas in 1987, they became the Hollywood power couple. When they called it quits eleven years later, they demonstrated unexpected class, residing in mansions across the street from each other and remaining amazingly friendly. After all, how many ex-husbands do you know who'd happily hang with their former wife and her much younger boy-toy hubby? Says Willis about the arrangement, "An actor friend of mine saw me, Demi, the kids and Ashton eating dinner and said, 'Man, this is evolution.'"

Esther "Eppie" Lederer (a.k.a. Ann Landers) and Julius Lederer
Ann Landers spent decades doling out snappy advice. But when announcing her divorce from her philandering husband in her column she admitted, "The lady with all the answers does not know the answer to this one." Lovers of irony everywhere were delighted, but Landers, always a lady, made a point of buying Lederer several pairs of skivvies and socks before vacating their apartment. Thank you, Ann, for keeping your ex in clean underwear-and choosing to not air your dirty laundry.

George Hamilton and Alana Collins
Before marrying rocker Rod Stewart, model Alana Collins cut her teeth on perma-tanned actor George Hamilton. Even though they divorced in the late seventies, the two sorted out their settlement on the back of a napkin over dinner and incurred only $750 in legal fees-a record for even the most amicable of Hollywood partings. Remaining close, the two co-hosted a talk show in the mid-1990's and, in 2005, began work on a reality show chronicling their comings and goings, plus those of Hamilton's most recent ex-wife and the children from their various couplings. Collins has said of their relationship, "We're best friends, and we're each other's family. We'll always be in each other's lives."

Prince Andrew and Sarah Ferguson
The seemingly perfect union between fun-loving royal son Prince Andrew and spunky redheaded Sarah Ferguson ended abruptly in 1992 amidst ubiquitous tabloid photographs of a topless Fergie having her toes sucked by another man. Eschewing a nasty breakup for an amicable parting, the two continued to live together as friends in Andrew's mansion, sharing meals, custody of their two daughters, and even continuing to send joint Christmas cards. Though Fergie finally moved out in 2002, "the happiest divorced couple in the world," as she called them, still engender hope and speculation for a royal reunion.

Barbie and Ken
Ending an era of perfect plastic bliss, Mattel announced in 2004 that Barbie and Ken were going their separate ways after 43 years. While rumors swirled that a certain newcomer named Blaine, the Australian boogie boarder, played a part in the split, the couple's business manager Russell Arons cited reluctance on Ken's part to make their union official. Arons added that the two were parting on good terms. Barbie and Ken, lacking mouths that actually open and expressions other than smiles, had no choice but to agree.

The Worst Breakups
These serve as cautionary tales, showing how emotions can flare and negativity can fester when wedded bliss crumbles.

Sylvia Plath and Ted Hughes
In terms of truly devastating breakups, one need look no further than the split between Sylvia Plath, poet and author of The Bell Jar, and her British poet hubby Ted Hughes. Over the course of their six-year union the pair suffered professional jealousy, Plath's depression, and Hughes' insensitivity before he left her for another woman. During the next six months Plath wrote some of her most enduring poetry (some comparing Hughes to a Nazi) before tragically ending her life. Her last works ensured that her ex (who would become Britain's poet laureate) would be demonized for the ages.

Woody Allen and Mia Farrow
Though they never actually tied the knot, the breakup of Woody Allen and Mia Farrow's ten-year union took the tabloids by storm with its unique mix of adultery, cradle-robbing, and creepiness. The details: It was revealed that Allen was having an affair with Farrow's 21-year-old adopted daughter, Soon-Yi Previn. Accusations of bad parenting flew from both parties, and a bitter battle ensued over their blended brood of adopted and biological children from their union and Farrow's pre-Allen days. Farrow received custody of the children, as well as support from ex-husbands Andre Previn and Frank Sinatra, the latter of whom helpfully offered to break Allen's legs.

Ron Perelman and Patricia Duff
In 1996, billionaire Revlon chief exec Ron Perelman and Democratic fundraiser Patricia Duff ended their 20-month marriage with much arguing about money. Duff, unsatisfied with a $30-million settlement, asked that the prenuptially agreed-upon $12,000 per month in child support for their 3-year-old daughter be bumped to over $100,000 per month (which included $3,000 a month for clothing and $1,500 for dining out). When Duff's request was denied, the couple moved on to a bitter custody dispute, which Perelman won in 2001. The five-year battle cost the couple upwards of $15 million in legal fees and caused their own judge to worry about the child's welfare given that her parents were focused on "attacking, torturing and slandering each other."

Rudy Giuliani and Donna Hanover
Though New York City mayor Rudy Giuliani displayed uncommon strength and valor during his tenure in office, his split from actress Donna Hanover was much less dignified. Shortly after announcing he had prostate cancer in 2000, the still-married Giuliani introduced the media to his "very good friend" Judith Nathan. A week later he announced his separation from Hanover-which came as a surprise to her. She berated Giuliani for "flaunting his mistress" and sought a restraining order barring Nathan from Gracie Mansion. The two finally settled their case in 2002 with Giuliani copping to "cruel and inhuman treatment."

Roseanne Barr and Tom Arnold
The 1994 divorce of Tom and Roseanne featured some well-publicized potshots: Roseanne initially filed for divorce claiming that she was a battered wife (allegations that Arnold strongly denied), only to withdraw charges later. Meanwhile, Arnold whined that Barr had left him with nothing, saying, "I didn't even leave with my clothes. She burned them." Barr's signature caustic response? "I'm not upset about my divorce. I'm only upset I'm not a widow."

Tracie Potochnik is a writer living in Providence, Rhode Island. In her best breakup ever, she got to keep the cat, the apartment, and the car.

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