U2 almost went broke staging the ZooTV tour. Tom Petty filed for bankruptcy. Mick Fleetwood of Fleetwood Mac was skint. Suede and Sting were ripped off by their accountants.
The list of rock stars who have lost millions because of bad business decisions stretches for miles. Here's a article from The Independent that details some of the financial carnage.
But pop stars have been making bad business decisions since the Beatles invested in the Apple Boutique in 1967, which closed six months later having lost around £200,000.
[M]ick Fleetwood's downfall was real estate. His property investment binge contributed towards him declaring bankruptcy in the mid-1980s (perhaps his staggering cocaine habit also had a lot to answer for). MC Hammer's investment in thoroughbred racehorses played a big part in the parachute pant-wearing rapper going broke in 1996. He should have learnt from rocker Ted Nugent, who also thought investing in racehorses was a good idea. Nugent had filed for bankruptcy in 1980.
But there have been success stories, too. For more, go here.