Hollywood Divorce Lawyers Tell All: Prostitutes, Cross Dressing, Drugs & More Shocking Split Secrets

It's always ugly, but in Tinseltown, divorce can be downright vicious. From the prenups to the payoffs, here are the stories behind the headlines...

Brad Pitt & Jennifer Aniston

MARRIED 5 YEARS, DIVORCED IN 2005

As all of Hollywood buzzed about Brad’s alleged affair with Angelina Jolie, Jen failed to capitalize on her hubby’s possible infidelity. Brad kept their production company, while Jen retained their house — big mistake, celebrity divorce lawyer Raoul Felder -- who did not work on the case -- says. “Film companies go on and on and make money off copyrights. But she got a house that never gets bigger or better and only needs repairs. She didn’t do as well as she could’ve.”

Kelsey & Camille Grammer

MARRIED 14 YEARS, DIVORCED IN 2011

After the now 56-year-old Frasier star dumped the Real Housewife for a 29-year-old flight attendant, Camille angrily turned down his $30 million settlement offer and demanded $50 million instead. Why? Spite, says Lombardo, who did not work on the case. “She may even get more than that; he traded her in for a younger model. She’s a scorned woman.” In the wake of the split, Camille leveled one particular accusation against him that got the headlines: that he liked to wear women's clothing!

Sandra Bullock & Jesse James

MARRIED 5 YEARS, DIVORCED IN 2010

Jesse might have a tough-guy image, but legal eagle Lombardo, who did not work on the case, says the cheating grease monkey rolled over when it came to custody of his and Sandra’s adopted son, Louis. “He didn’t fight for anything — not for custody nor to invalidate the prenup, which aren’t always air-tight. But Jesse just hung his head and walked away.”

Tiger Woods & Elin Nordegren

MARRIED 6 YEARS, DIVORCED IN 2010

After the golf pro’s slew of torrid affairs came to light, his jilted wife renegotiated her prenup and eventually walked away with upwards of $100 million, but only under one condition: that she never discuss their marriage. Divorce attorney Danielle Petitti, who did not work on the case, says that Tiger’s hectic schedule would have meant Elin had a good chance at obtaining full custody. But lawyer Lombardo speculates that Tiger’s settlement helped ensure access to his two young kids. “Tiger is essentially paying for custody and privacy.”

Madonna & Guy Ritchie

MARRIED 8 YEARS, DIVORCED IN 2008

Rumors swirled during their 2008 split that Madge had cheated on her director husband with N.Y. Yankee Alex Rodriquez. Adding insult to injury, the hunky British filmmaker reportedly netted far less than half of the Material Girl’s $500 million fortune in the divorce. But don’t cry for Guy. “If he got around $80 million it was worth it, because he’s free and his privacy is protected,” explains Lombardo, who did not work on the case.

Paul McCartney & Heather Mills

MARRIED 6 YEARS, DIVORCED IN 2008

In this ugly split, Heather demanded $250 million in alimony, saying she needed $80,000 to spend on wine and $1 million a year for vacations. “Had she not been so greedy with the initial request, the judge may have awarded her more,” Lombardo, who did not work on the case, says. But don’t weep for this ex — Sir Paul eventually forked over $48.6 million.

Alec Baldwin & Kim Basinger

MARRIED 9 YEARS, DIVORCED IN 2002

The 30 Rock funnyman didn’t draw many chuckles when a verbally abusive voice-mail he left for his young daughter came to light after an ugly custody battle with Kim. “Alec did something irreconcilable — he picked on a kid,” says Felder, who did not work on the case. “When he called his daughter a ‘thoughtless little pig,’ he lost his case right there, at least in the court of human opinion.”

Matt Lauer & Annette Roque

MARRIED IN 1998, DIVORCE PAPERS FILED 2006, STILL MARRIED

According to divorce lawyers, one false move in his personal life could cost the Today show host dearly—because his model wife Annette allegedly compiled a list of his “other women” when she slapped him with divorce papers in 2006. Annette withdrew the divorce petition a few weeks later but her marriage to Matt has been rocky for years since she learned he’d been having a secret affair with a married woman just months before they wed, sources say.

Rachael Ray & John Cusimano

MARRIED IN 2005, STILL MARRIED

Sources claim the TV chef never signed a prenup with John, an entertainment lawyer who has helped broker many of her most lucrative deals. That means Rachael could lose half of her billion-dollar empire. And not even her husband’s bizarre sexual shenanigans, reported by the National Enquirer, could save her fortune in a divorce, according to sources. “John could walk away with a lot of money despite the cheating,” a legal insider said.

Kelly Rutherford & Daniel Giersch

MARRIED IN 2006, DIVORCED IN 2010

The Gossip Girl star suffered a nasty divorce and custody battle with German entrepreneur Daniel. They fought over son Hermes and traded nasty accusations. An attorney said at the time, “These two are fighting to see who can make each other look the worst, and they’re doing a pretty good job. The problem is that their child has become a pawn in the battle between them, and he’ll be the biggest loser of all.” In August 2012, a California judge ruled that a 50/50 custody arrangement should remain, and the children should live in France with Giersch and attend school there, with Rutherford travelling to visit them. In June 2013, Rutherford filed for bankruptcy due to her debts from legal fees.

Mel Gibson and Robyn Moore Gibson

MARRIED IN 1980, DIVORCED IN 2011

After photos of Mel Gibson looking cozy with singer Oksana Grigorieva surfaced in 2009, the actor’s long-suffering wife, Robyn, filed for divorce. When the divorced was finalized in 2011, Robyn walked away with a record settlement of about $400 million, because, sources said, the couple didn’t sign a prenup when they wed in Australia in June 1980. Divorce lawyer Seymour Reisman, who didn’t work for the couple, also predicted before they split that Robyn knew all of Mel’s secrets—so there was no way she wouldn’t walk away with half his fortune!

Shania Twain and Mutt Lange

MARRIED IN 1993, DIVORCED IN 2010

Lawyers predicted the singer and her music producer husband had a complicated divorce. The Swiss-based couple had built a joint billion-dollar empire with assets in Shania’s home country of Canada, the United States, New Zealand and Switzerland, where they owned a $15 million chateau. But their rock-solid 14-year marriage exploded in May 2008 when Mutt reportedly cheated with their friend and house manager Marie-Anne Thiebaud — however she denied the claims. While the terms of their Swiss divorce were sealed, attorney Seymour Reisman said, “One thing is certain – their son Eja is going to be well taken care of.” And it was a strangely happy ending for Shania as she married Marie-Anne’s ex-hubby, Frederic Thiebaud!

Morgan Freeman and Myrna Colley-Lee

MARRIED IN 1984, DIVORCED IN 2010

After the Oscar winner cheated with Mary Joyce Hays, Morgan was slapped with divorce papers by his wife Myrna Colley-Lee in July 2008, who got the help of legal eagles in Charleston, Miss., where the couple owned a 126-acre horse farm. “These guys were no country bumpkins,” a source said. “They had the smarts to communicate with big Hollywood guns who helped direct the country gentlemen into securing a big-city payday for Myrna!” Myrna reportedly walked away from her 24-year marriage with a cool $170 million, plus the couple’s $7 million home in the British Virgin Islands.

Charlie Sheen and Denise Richards

MARRIED IN 2002, DIVORCED IN 2006

Charlie and Denise Richards still battled over custody of their daughters Sam and Lola after they were legally divorced. And it was Denise’s allegations that Charlie was addicted to gambling, drugs, prostitution and porn that fueled their bitter split. “Denise had it in for this guy after what she discovered about his sex life. It was far worse than anything she dreamed she’d find, and she really used it against him,” said attorney Seymour Reisman, who didn’t represent the couple. The odd part is, as RadarOnline.com readers know, Denise is now raising the former “Two and a Half Men” star’s twin boys from his third wife, Brooke Mueller, along with her own two girls by Charlie.

Larry King and Shawn Southwick King

MARRIED IN 1997, STILL MARRIED

The talk show king and his wife both filed for divorce in 2010, but then dropped it. Hollywood divorce lawyers were salivating at the prospect of another for King, who’s been wed seven times! Shawn allegedly carried on a year-long extramarital affair right under Larry’s nose with their young sons’ baseball coach. Southwick's sister also slammed rumors that she had an affair with King! "This is so ludicrous," Shannon Engeman said. Larry’s worth an estimated $100 million, and the couple did not sign a prenup when they wed, meaning Shawn could walk away with $50 million if they split. Hollywood divorce lawyer Kelly Chang Rickert, who does not represent either of the Kings but knows California divorce law, said, “With no prenup, the fact that she may have cheated right under his nose won’t get Larry off the hook.”

Hillary Clinton and Bill Clinton

MARRIED IN 1975, STILL MARRIED

According to sources, Hillary once secretly met with a top lawyer and drew up divorce papers after getting fed up with his cheating. She also reportedly compiled a list of his lovers to use as ammunition in the split! “That bombshell disclosure has been dished by divorce lawyers in the know,” a source said. Hilary later decided to run for the Senate in New York and become Secretary of State, so she abandoned divorce plans. Famed New York divorce lawyer Raoul Felder – who’s not involved in the Clinton case – said: “If Hillary had divorce papers written up but not filed, the lawyer must keep them secure for at least seven years. That is the law. But they will always remain secret. Even if Hillary died, the lawyer can never divulge their contents because it falls under privileged information.”

Christie Brinkley and Peter Cook

MARRIED IN 1996, DIVORCED IN 2008

Christie’s divorce from philandering hubby Peter Cook stands as one of the nastiest ever. Details of Peter’s affair with his teenage assistant Diana Bianchi were exposed in court, along with his porn addiction and other embarrassing sexual habits. “But Christie could have been hurt even more if the case had continued,” said a source close to the couple. They settled the case before Cook could publicly smear Christie, an insider said. The “Uptown Girl” agreed to give $2.1 million to Cook, but kept properties in the Hamptons and was awarded custody of their kids.

Julia Roberts and Danny Moder

MARRIED IN 2002, STILL MARRIED

Cameraman Danny Moder was a married man when he met Julia Roberts on a movie set in 2001. But not for long! After divorcing his wife Vera, he wed the “Pretty Woman” star in July 2002. The two

appear to be blissfully happy raising their three kids. But there could be trouble ahead. As Beverly Hills celeb divorce attorney Steven Stolar, who didn’t represent the couple, said: “In my experience, when a couple gets together after cheating on a previous spouse, there are trust issues. Julia might worry that because Danny strayed once, he’ll stray again.” Sources are sure Julia has an iron-clad prenup!

Bill Murray and Jennifer Butler

MARRIED IN 1997, DIVORCED IN 2008

In explosive court papers, Jennifer charged the former “Saturday Night Live” star was abusive and a sex maniac, as well as being addicted to marijuana and alcohol. The former costume designer also claimed Bill left threatening messages on her answering machine which their children heard – and once punched her in the face! But Jennifer had her own problems with booze; she reportedly spent 45 days in an Arizona rehab clinic. She wound up settling for $7 million, sources said. Attorney Seymour Reisman, who didn’t represent either party, noted: “Bill’s wife really wanted to make him pay. But in the end, she realized that he had just as much on her as she did on him.” Bill later said the divorce "was devastating." "I was just dead, just broken," he added. "When you're really in love with someone and this happens _ I never had anything like this happen," he said. "It's like your faith in people is destroyed because the person you trusted the most you can no longer trust at all... The person you know isn't there anymore."

Star Jones and Al Reynolds

MARRIED IN 2004, DIVORCED IN 2008

The former co-host of “The View” protected her assets with a prenup before she married banker Al Reynolds in November 2004 – and it paid off! The prenup reportedly said that if the legal eagle’s marriage ended before hitting the five-year mark, Al – who was dogged by rumors he’s gay – would receive none of her $10 million fortune. Star reportedly agreed to a small payoff, and attorney

Seymour Reisman said, “The key here is the iron-clad prenup, and that protected her assets.”

Jessica Simpson and Nick Lachey

MARRIED IN 2002, DIVORCED IN 2006

This couple didn’t have a prenup and Jessica was making more than her 98 Degrees star husband at the time of their breakup. But instead of opting for California’s customary 50/50 split, sources say financially strapped Nick took a quick $10 million settlement before the divorce was final. It was much less than half of Jessica’s estimated $36 million fortune. Nick reportedly didn’t want a protracted court battle with his former “Newlyweds” co-star wife.