Brad Pitt & Angelina Jolie — The 8-Year War

The Brangelina divorce, filed in 2016, has evolved into the longest and most expensive celebrity legal war, now in its tenth year — surpassing the #3 item's duration by over 4 years. The primary dispute revolves around Chateau Miraval, a $164 million French winery co-owned by the couple. Jolie sold her 50% stake to a Stoli Group subsidiary, prompting Pitt to sue, claiming she needed his approval. The custody battle over six children generated over 1,500 court filings, with legal fees exceeding $10 million per side. This isn't just a divorce; it's a decade-long legal war of attrition fought through proxy companies and sealed court documents, costing an estimated $100 million combined.