May-December Celebrity Divorces

On Nov. 17, 2011, after six years of marriage, celebrity couple Demi Moore and Ashton Kutcher filed for divorce. The pair had made headlines when they first emerged as a couple, and very few of those headlines ran without pointing out the 16-year age difference between the two of them.

The age gap between Moore and Kutcher made their union a classic May-December romance, and the list of celebrities who have engaged in such unions is long. Almost as long, however, is the list of such couples who couldn’t keep their marriages together. Divorces lawyers have full coffers thanks to the dissolution of such May-December celebrity unions, particularly when there was no pre-nuptial agreement in place.

What are some notable May-December celebrity divorces? Click ahead and find out.

By Daniel Bukszpan
Posted 18 November 2011

When the UK’s Prince Charles married Diana Spencer in 1981, the whole world was watching. Literally. Aside from the 3,500 guests who came to St. Paul's Cathedral in London to watch the couple exchange vows, hundreds of millions more across the globe watched the couple wed on television. It was a storybook union, or so it seemed.

The Prince, who was 13 years his bride’s senior, had been carrying on an affair with Camilla Parker-Bowles; Charles and his wife finally divorced in 1996. In the settlement, she was awarded £17 million, the equivalent of $27 million and equal to $39 million today.

Actor Kelsey Grammer of “Cheers” and “Frasier” fame is no stranger to the altar, or to the divorce lawyer for that matter. He has been married four times, and the longest of these unions was his 14-year marriage to Camille Donatacci, a dancer, model and actress 13 years his junior who is best known as a cast member on “The Real Housewives Of Beverly Hills.”

In 2010 she filed for divorce citing irreconcilable differences, and the divorce was granted in February 2011. Although the settlement has not yet been made public, Camille Grammer said in her court filings that the couple’s shared assets may be worth as much as $20 million.

When actors Demi Moore and Bruce Willis divorced in 2000 after 13 years of marriage, people were shocked. The only thing more shocking was when it was revealed that her new partner was the star of “That 70s Show,” Ashton Kutcher. Besides the 16-year age gap they seemed like an odd fit, and the unconventional relationship they maintained with Willis raised more than a few eyebrows, particularly when it was revealed that they all went on vacations together.

Still, it seemed to work for some intangible reason, and the couple finally wed in 2005. However, there was trouble in paradise, including allegations that Kutcher had been unfaithful. Eventually the strain became more than they could handle and Moore announced her intention to end the marriage in November 2011.

Real estate mogul, reality television star and former potential presidential candidate Donald Trump was first married to Czech former athlete Ivana Trump. After 15 years of marriage the pair had a very public and very messy divorce in 1992, which cost him $25 million.This might have discouraged a lesser man from ever dating again but “The Donald” is no shrinking violet. One year later he had a new bride on his arm in the person of actress and socialite Marla Maples, 17 years his junior.

In 1997, the couple announced their split. This took place just shy of the five-year mark, and had the marriage crossed that particular threshold the prenuptial agreement would have allowed her to receive a substantial but undisclosed percentage of the mogul’s multi-billion-dollar fortune. Luckily for him, they beat the filing deadline, making her eligible instead for a mere $5 millionsettlement.

Larry Fortensky is a former construction worker best known as the final husband of legendary actress Elizabeth Taylor. The pair met at the Betty Ford Clinic in 1988 and married in 1991 at a ceremony at Michael Jackson’s Neverland Ranch. The star-studded event was attended by such luminaries as Nancy Reagan, Liza Minnelli and Merv Griffin.

At the time, more than a few people speculated that Fortensky, nearly 20 years Taylor’s junior,  was only after the actress’ money, and indeed when they were married she frequently showered him with expensive gifts. It was later revealed he had signed a pre-nuptial agreement that stipulated he would be awarded $1 million if the marriage lasted at least five years. The union lasted until 1996, five years after the wedding had taken place.

Taylor died in 2011 and Fortensky vehemently denies that he was ever after her money. “I have wonderful memories of my time with Elizabeth,” he said, “and I will treasure her memory forever.”

During the 1970s, singer Rod Stewart had a reputation as a notorious womanizer. However, the love-‘em-and-leave-‘em scoundrel who sang “Hot Legs” and “Do Ya Think I’m Sexy?” was eventually ready to change his ways and settle down. In 1990 he embarked upon his second marriage, this time to leggy Australian supermodel Rachel Hunter.

Although she was a full 24 years younger than him, the union far outlasted any other relationship in which he had been involved, and for a long time it seemed like he had found permanent happiness. Sadly, it was not to be, and the couple divorced in 2006. Details of the settlement were never disclosed.

Former Beatle Paul McCartney’s first marriage was to Linda Eastman in 1969. He regularly described her as the love of his life, and indeed in the almost 30 years in which they were married they were inseparable. Tragically, she died of breast cancer in 1998 at the age of 56, and by all accounts it was a devastating blow to the musician. However, one year later he met model Heather Mills, who was 26 years younger than him and was 2 years old when the Beatles broke up.

The pair married in 2002 and they began to clash almost immediately. They separated in 2006 and during the extremely bitter divorce proceeding Mills requested a settlement of $250 million.The judge hearing the case characterized many of her requests as “ridiculous” and “exorbitant” and ultimately she was awarded $49 million, which included a lump sum of $33 million and $15 million in real estate holdings.

Billy Joel’s 1985 compilation album, “Greatest Hits Volume I & Volume II,” has sold a Recording Industry Association of America-certified 23 million copies, making him one of the most successful musicians in the world. However, he was less lucky in love than he was on the Billboard charts, and his first two marriages, including his union with supermodel Christie Brinkley, had flamed out spectacularly. Would the “Piano Man” ever find happiness?

In 2004, he married his third wife, television food critic and chef Katie Lee, 32 years his junior and just four years older than his daughter Alexa Ray Joel. Five years later, the 27-year-old and her husband separated, and she was seen in the arms of Israeli clothing designer Yigal Azrouel. Although many of the particulars of the divorce settlement remain undisclosed, Lee is known to have received a four-story townhouse in New York City, which she sold for almost $12 million.

Legendary Rolling Stones bassist Bill Wyman didn’t get much of the spotlight when he was in the band, leaving it to the infamous frontmen Mick Jagger and Keith Richards. However, in 1983, at the age of 47, he became tabloid bait for the first time when he began dating Mandy Smith, who was 13 years old at the time, a full 34 years younger than him. In his 1990 autobiography “Stone Alone,” Wyman wrote "She took my breath away...She was a woman at thirteen..."

The couple married in 1989, when she was 18 and he was 52, but the bliss didn’t last. They divorced 23 months later and Smith won an $880,000 settlement. It is perhaps for the best that the union didn’t work out; in 1993, just two years after the divorce, Wyman’s 31-year-old son Stephen was reported to be romantically involved with Smith’s 49-year-old mother, which might have made the holidays a little awkward.

Playboy magazine founder Hugh Hefner has had his pick of nubile centerfold models sunning themselves at his mansion’s poolside. However, the top of the mountain can be a lonely place, and despite being surrounded by beautiful young women for almost his entire adult life, true love was hard to come by. He had been married once before during the 1950s, but in 1989 he married Playmate of the Year Kimberley Conrad, who was 36 years younger than him.

The couple separated nine years after marrying but didn’t divorce until 2009, a full 11 years after their separation. Hefner claimed he filed for divorce after Conrad sued him for $5 million and claimed that he had been paying her $250,000 a year per their extremely rigorous pre-nuptial agreement. The day after the divorce was finalized in March 2010, Hefner announced his intention to marry the December 2009 Playmate of the Month, Crystal Harris, who is 60 years his junior. However, five days before the wedding Harris called it off, and Hefner remains a bachelor today.