5 of Hollywood’s Most Expensive Celebrity Divorces – Including Brangelina

Celebrity marriages often come with massive fortunes, and when they end, the financial fallout can be staggering. From billion-dollar empires to multimillion-dollar settlements, these high-profile divorces reshaped some of Hollywood’s most powerful partnerships.

When wealthy celebrities split, the headlines often focus on who gets what. Over the years, several high-profile divorces have involved massive estates, expensive settlements, and complex legal disputes.

Here are five of Hollywood’s most expensive celebrity divorces:

1. Kanye West and Kim Kardashian

Kanye West and Kim Kardashian were worth a combined $2.1 billion when their divorce was announced in 2021 after seven years of marriage.

West had a $1.3 billion estate, while Kardashian was worth $780 million. The couple shared $70 million in joint assets, including several luxury homes.

Ultimately, Kardashian and West finalized their divorce in November 2022. In their agreement, West agreed to pay $200,000 in monthly child support for their four children, joint custody, and waiving of spousal support. They also split their assets based on their prenup, with shared expenses for their kids's security detail and schooling.

2. Madonna and Guy Richie

Madonna and British director Guy Ritchie married in 2000 and divorced in 2008 after nearly eight years together.

According to reports, Ritchie received between $76 million and $92 million as part of the settlement. The payout included property and other shared assets.

At the time, the divorce ranked among the most expensive in the entertainment industry, reflecting Madonna’s decades of global success as a recording artist and performer.

3. Demi Moore and Bruce Willis

Demi Moore and Bruce Willis were one of Hollywood’s most recognizable couples in the 1990s. Moore starred in films like "Ghost," while Willis led the "Die Hard" franchise.

After ten years of marriage, the couple divorced in 2000. Reports place their settlement at approximately $90 million, making it one of the largest actor divorces at the time.

Despite the split, Moore and Willis remained publicly supportive of one another and continued co-parenting their three daughters.

4. Paul McCartney and Heather Mills

Paul McCartney’s divorce from Heather Mills became one of the most closely followed splits in the music world.

Mills initially sought a significantly larger sum at $250 million, but in 2008 she was awarded approximately $48.6 million. The former couple share a daughter, Beatrice McCartney.

Although the final amount was lower than some expected, the case drew intense media attention and remains one of the most talked-about divorces involving a music legend.

5. Brad Pitt and Angelina Jolie

Brad Pitt and Angelina Jolie called it quits in 2016. Soon after, Jolie accused Pitt of failing to meet his child support obligations.

In her initial filing, Jolie requested physical custody of their six children.

The legal battles did not end there. The former couple also went to court over their winery, Miraval, in which they once held equal 50-50 stakes. In 2021, despite reportedly agreeing not to sell their shares without consulting each other, Jolie sold her portion to Tenute del Mondo, the wine division of the Stoli group controlled by Russian billionaire Yuri Shefler, for $67 million.

Divorce is never simple, but in Hollywood, it can involve staggering sums of money and years of legal proceedings. From multimillion-dollar settlements to disputes over shared businesses and properties, these splits reshaped some of entertainment’s most powerful partnerships.

While the headlines often focus on personal drama, the financial consequences reveal just how high the stakes can be when celebrity marriages come to an end.