Guy Ritchie and Madonna

A $27 million divorce settlement may seem generous to some, but not Guy Ritchie. When he and Madonna parted ways after eight years of marriage, he reportedly scoffed at that figure, knowing he had more to gain because even though Madonna was worth an estimated $500 million, she had never asked Ritchie, worth an estimated $45 million, to sign a pre-nup. And good thing, because he more than tripled the first offer and reportedly walked away with a cool $92 million. How’s that for patience paying off?

Mel and Robyn Gibson

It’s hard to put a price tag on being married to Mel Gibson and his famous temper for nearly 30 years, but for his ex-wife, Robyn, that price was reportedly $425 million – and then some. Without a prenuptial agreement on record, Gibson lost half of his earnings during their marriage and was also ordered to pay Robyn half of his residual film earnings for the rest of his life when the two divorced in 2011.

Reese Witherspoon and Ryan Philippe

“Legally Blonde” star Reese Witherspoon was “legally blind” when it came to love – and paid the price. At the beginning of her seven-year marriage to Ryan Phillipe, the two young actors were just starting to make their mark on Hollywood. By the time they divorced, Witherspoon had won an Academy Award for her role in “Walk the Line” and was raking in $20 million per movie, while Ryan hovered around $2.5 million per film. Without a prenup in place, Philippe was entitled to half of her earnings under California law.

Rosanne Barr and Tom Arnold

Rosanne Barr should have listened to her lawyer. Instead, she fired her attorney for the mere suggestion that she and Tom Arnold sign a prenup when they got married in 1990. Fast forward four years when the couple divorced and Tom walked away with $50 million in his pocket. That must have helped get him a date.

Paul McCartney and Heather Mills

Former Beatle Paul McCartney should have taken the band’s famous song “Tomorrow Never Knows” a bit more seriously when he decided against asking  environmentalist Heather Mills to sign a prenup before the couple married in 2002, despite the fact that he was worth an estimated $660 million. As a result, Mills, McCartney’s second wife, walked away with $35 million. He couldn’t have been too fazed by the payout because he opted out of a prenup – again! – before his third marriage to New York businesswoman Nancy Shevell in 2011.

Katy Perry and Russell Brand

Without a pre-nup in place, Russell Brand could have been set for life after the funnyman and Katy Perry divorced. However, according to reports, he refused $20 million in their settlement, which was half of the pop star’s earnings during their 14-month marriage. Reports also indicate Perry signed the divorce papers with the signature smiley face in her last name. No wonder she was smiling.