3. Broke: Lindsay Lohan Is Living Lavishly And Earning Very Little

Occasional actress and permanent tabloid fixture Lindsay Lohan started to hit the skids when she was in her early 20s, and she has really never stopped stumbling since then. Lindsay has so far avoided having a total financial and professional collapse so far, but she also seems like she is always on the verge of that collapse too. She doesn’t get much work in the entertainment industry anymore, and while she obviously must have dialled down her spending a bit since she hit her career peak she still seems to have some pretty extravagant taste without the actual money to back it up. Lohan has been rumored to be working as a “yacht girl” for quite a long time now, and seeing as she has been able to stay afloat when she doesn’t appear to actually be working that seems like a reasonable explanation. But eventually the novelty of being able to buy a date with LiLo is going to wear off, and once that money well has dried up she’ll be in serious trouble.

4. Broke: 50 Cent Went From A Net Worth Of $140 Million To Being $36 Million In Debt

When it comes to earning and losing millions of dollars, very few celebrities illustrate that earning a ton of money doesn’t mean that you’ll keep that ton of money more than rapper 50 Cent. 50 Cent is still one of the most successful hip hop artists of all time, with his net worth at one point being estimated at over $140 million dollars, but he somehow managed to lose it all and then some in just a few years. Eventually 50 Cent wound up declaring bankruptcy, claiming that he was $36 million dollars in debt, and his meteoric rise and even more shocking fall were so extreme that Reelz actually filmed a documentary about his insane financial situation. The money-obsessed rapper filed for bankruptcy in 2015 and appears to have rebounded a little bit since, but anyone who managed to blow through anywhere from $200 million to half a billion dollars in less than a decade doesn’t seem to have very reliable money management skills.