Brad Pitt and Jennifer Aniston — $60 Million
Kicking it off with one of the most popular couples of the early 2000s. Brad Pitt (Fight Club) and Jennifer Aniston (Friends) met in 1994 and instantly sparked a connection. They began dating in 1998. From then on, every move the pair made was under a microscope as the tabloids couldn’t get enough of the high-profile couple. Pitt — who had recently ended a relationship with Seven co-star Gwyneth Paltrow — wed Aniston two years after the couple began dating in a private wedding in Malibu. Amidst rumors of Pitt getting romantically involved with a co-star (more on that in a bit), the pair announced their divorce in 2005. The paperwork was finalized later that year, and the couple reportedly remained cordial with each other even after the split.
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Alex Rodriguez and Cynthia Scurtis — $12 Million
Former three-time MLB MVP Alex Rodriguez has built a catalog of ex-flings and high-profile relationships which would put the 1920s New York Yankees to shame. Perhaps his messiest union is the one with his first wife, psychology graduate Cynthia Scurtis. The pair were married in 2002, and had two children together (both daughters). In 2008, the marriage fell apart after Scurtis accused Rodriguez of having extramarital affairs. The divorce settlement reportedly cost A-Rod — the No. 1 career earner in MLB history — around $12 million.
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