Anna Nicole Smith
Anna Nicole Smith is one of the most famous Playboy bunnies in the history of the magazine. Thanks to her career and marriage to businessman J. Howard Marshall II, Smith, managed to make almost half a billion buckeroos.
Unfortunately, when the playboy bunny tragically passed away in 2007, the courts ruled that none of her wealth would be inherited by her little girl, Dannielynn. Not one single cent from her $475 million fortune. The only thing Smith left behind was the legacy of her outrageous, over-the-top behavior.