Courtney Love
Courtney Love is an actress and musician that just can’t keep out of trouble. Even before her tax troubles began, she had been abusive to Kurt Cobain on more than one occasion. That, plus her drug addiction, had made her the target of all kinds of conspiracy theories regarding the death of Nirvana’s lead singer.
Anyway, in 2012, her tax troubles came to light. She had avoided paying hundreds of thousands to the IRS and had to pay an additional $27 million in court fees. Don’t feel too bad for The People vs. Larry Flynt actress since she still has about $100 million in assets.