Lindsay Lohan
The Mean Girls actor has been in trouble with the IRS an impressive three times. In 2013, the State of California claimed Lohan owed $56,717.90 for unpaid income tax for 2011. She also had unpaid federal taxes bills totaling $140,203.30 and $93,701.57 from 2010 and 2009. Fellow troubled star Charlie Sheen gave Lohan $100,000, which she used to pay off some of her debt to Uncle Sam. But three months later, he publicly complained she never even thanked him for the check. She reportedly then sent him a bouquet of flowers.
