Val Kilmer – Bankrupt Celebrities
While you might think Val Kilmer's downfall came from being the Batman with fake nipples built into his bat suit, in reality, his real problems arose when he didn't pay his taxes.
In 2009, he was slapped with a $533,000 tax lien -- at which point he tried to sell his $33 million ranch for just $18 million to eliminate some of the debt.
Unfortunately, no one wanted it, and even after he'd paid off his former lien, he was slapped with a second one for $500,000 in 2011. Ouch.