14. Lindsay Lohan
2012 was the year of our lord when hard-partying Lindsay declared bankruptcy after almost a decade of drug abuse, uncontrolled spending and all kinds of shenanigans. Charlie Sheen gave her 100k to try and hold her over but that wasn’t enough as she already owed over a million to the IRS…Plus, when Charlie gives you money, it probably comes with a clause that you have to spend it on even harder partying, right?
Lohan is the perfect representative of the spoiled, fun-loving Hollywood brat stereotype who doesn’t know when to call it a day or at least slow down. She was earning some really decent cash back in the day, and instead of putting at least some of it in some wise investment, she continued to spend, spend, spend. She bought a super-expensive condo in Hollywood but still spent months living in Chateau Marmont, with her condo just minutes away, amassing a huge bill.
In addition, the IRS was on her back for unpaid taxes on three occasions – in 2009, 2010 and again in 2011, for amounts that went from $50K to $140K.