Homeless celebs? At times, the trip from career high to down and out is alarmingly short, and it happens far more often than you think. If you’ve never been rich, then it tends to seem like money would be the solution to all your problems. There’s no denying that available funds are the solution to many an issue, but it’s a mistake to think it would make all your problems go away. Even when you add fame, money, and celebrity together, the real-life stories of celebs who ended up on the street prove that you can lose it all no matter how high up you are in society when you begin.