Digging into Macaulay Culkin's financial history would give any accountant an instant migraine. From the tens of millions he was raking in as a child, there came a decline that was at times slow, and at times painfully quick. Both his father and mother fought over the control over his finances, and much of it was gobbled up in legal fees just trying to keep some from himself.
That's not to mention the fact that he really wasn't working much, either, and the lavish lifestyle and high-profile friends he was hanging out with meant that you would think he'd be easily broke by now. In fact, he's still worth a massive $15 million dollars. Sure, that might not sound like a lot, but for a guy who's been pretty much doing what he wants his whole life, it's pretty good. We'd take it.