Madonna and Guy Ritchie
After eight years of marriage, the pop icon filed for divorce from her director husband, citing his "unreasonable behavior." More than a decade older and considerably wealthier than Ritchie, Madonna's publicist confirmed that she ponied up the lump sum almost a fifth of her estimated $500 million net worth to end the union.
Britney Spears and Kevin Federline
Even before the divorce, Spears was no stranger to shelling out cash for Federline his occupation at the time of their marriage was listed as "pizza delivery boy and dancer." She reportedly even paid for her own five-carat diamond double-banded engagement ring.
Jessica Simpson and Nick Lachey
When the two Newlyweds filed for divorce, critics speculated that the one-time boy band member would seek spousal support from Simpson, who was worth more than $35 million at the time. Despite his much smaller net worth, he openly refused to request a payout, even turning down a $1.5 million settlement offer from Simpson's dad.
Christina Aguilera and Jordan Bratman
Shortly after announcing their split, headlines surfaced that the chanteuse had moved her new boyfriend, Matthew Rutler, into her mansion the same mansion that Bratman refused to vacate. While the couple did sign a prenup, leaving Bratman with nothing, it's been reported that Aguilera conceded to give her ex an undetermined settlement when the divorce was finalized. He then moved out of the residence.
Sandra Bullock and Jesse James
The world was shocked when Sandra Bullock's motorcycle-riding, bad-boy husband's secret affair with a tattooed Nazi-saluting stripper was revealed. When Bullock quickly filed for divorce, James, in a last ditch effort to save face, stated he would refuse spousal support. A nice gesture, except that he wasn't entitled to any in Texas, a spouse must be married 10 years to qualify for alimony.
Reese Witherspoon and Ryan Philippe
America's sweetheart filed for divorce after eight years of marriage, while rumors of Philippe's infidelity — he reportedly cheated with his Stop-Loss costar Abbie Cornish — hit the tabloids. By California state law, he was entitled to half her earnings, but during divorce proceedings, Witherspoon, an Oscar winner and more profitable talent, asked that the court deny Philippe any spousal support.
Kate Walsh and Alex Young
After only 15 months of marriage, Young, a movie exec, filed for divorce from the popular TV actress. Walsh counter-filed a few weeks later, and a nasty battled ensued. In the end, in an effort to decide the distribution of community property — including furniture and artwork — they flipped a coin to see who got first pick.
Martina Navratilova and Toni Layton
After eight years together, Layton claimed she was unceremoniously dumped when the tennis player changed the locks on their Florida home. When Layton demanded she be compensated for her time in the relationship, Navratilova offered her $200,000 to walk away. Layton, who left her husband for Navratilova, in turn sued and threatened to expose skeletons in the pro's closet. Navratilova sweetened the deal by $2.8 million and Layton kept her mouth shut.
Rosanne Barr and Tom Arnold
When the two comics married in 1990, her lawyer suggested she have Arnold sign a prenup. She fired her attorney for the suggestion. For the sitcom star, this turned out to be a bad business move — four years later, the couple split and Arnold left with a major chunck of her earnings.
Anna Faris and Benjamin Indra
The two actors married in 2004, with Faris' star already on the rise. Within the next three years, the comedienne established a place on Hollywood's A-list while Indra's career quickly went nowhere. Faris eventually left him behind though not empty-handed.
Elizabeth Taylor and Larry Fortensky
The late Hollywood icon met her eighth and final husband, a muscle-bound construction worker, 20 years her junior, while both were in rehab at the Betty Ford Center. Eight years later, during their divorce, he asked for $6 million. She gave him a cool mil and sent him packing.
Kim Basinger and Ron Britton
When the marriage between the blonde starlet and her makeup artist husband dissolved, Britton sued for alimony. Basinger accepted gracefully saying that Britton had taken care of her when she first started in show business — she'd reportedly asked Britton, who's birth name was Ron Synder, to change his last name to "something with a B" in order to match monograms on a set of luxury luggage.
Anne Heche and Coley Laffoon
One of the nastiest celebrity splits, Laffoon and Heche battled over the ownership of yoga mats and slung dirt to any media outlet willing to listen. He called her mentally unstable and she exposed his penchant for porn and strippers, branding him a "lazy" deadbeat on late night talk shows. Regardless, Heche toted the bigger paycheck, allowing Laffoon's bank account to surge.
Janet Jackson and René Elizondo
Together for more than 13 years, the singer has never denied that Elizondo was an instrumental part of her life and career. Still, the two who had kept their relationship and marriage secret for several years, began to increasingly argue over finances before calling quits. During the divorce proceedings, Elizondo claimed he was forced into signing a prenup. He was eventually awarded a settlement.
Jennifer Lopez and Chris Judd
The pop icon met Judd on the set of her music video, "Love Don't Cost a Thing." He was her backup dancer and choreographer, and she was already on the road to becoming a performing legend when the two married. Eight months later, however, the two went their separate ways, and he walked away with a small but impressive portion of her fortune.