So famous was the King of Pop that he was tagged as the highest-paid entertainer twice by Forbes. Unfortunately, lawsuits and large spending accounts plagued his estate before he died in 2009.
By 1990, the star filed for bankruptcy claiming $20 million in debt. The Internal Revenue Service sued him in 2005 for failing to pay the $1.8 million he owed in taxes on a house he sold.
In the early 90s, the Batman actress was the center of several nasty lawsuits that quickly drained her finances. She also sunk $20 million into a small Georgia town she’d hoped to turn into a tourist stop or production studio.
Stephen, the youngest of the Baldwin brothers, doesn’t seem to like paying taxes. This issue has caused him serious financial woes. At one point, he was arrested and served five years of probation for three consecutive years of failing to pay taxes.