If you’ve never heard of famed “Gonzo” journalist Hunter S. Thompson you’re probably not alone. He was always more of a cult figure than a big-time celebrity, even if he was the author of such seminal books as Hell’s Angels and Fear and Loathing in Las Vegas. However, lots of actual big-time celebrities have heard of “The Good Doctor,” as Hunter styled himself and were huge fans of his. In fact, Johnny Depp, who played Thompson in the movie version of Fear and Loathing, was such a fan of his fellow Kentucky Colonel that when Thompson died, Depp shelled out a cool $3 million to shoot Thompson’s ashes out of a giant cannon, in accordance with the writer’s last wishes.

All of this brings me to the point of today’s exercise: regardless of whether you think spending $3 million on a weird dying wish is a good idea or not, the very rich are very different from you and me and can do such things on a whim simply because they want to. Well, that’s to say they can do such things for no good reason at all until they do them so many times they end up just like your average Joe — broke. Depp himself is teetering on the edge of bankruptcy as you read this precisely because of expensive stunts, overzealous purchases, and an ugly little divorce to Amber Heard. He’s not quite there yet — the man was once worth almost $400 million after all, but plenty of stars have gone straight over that edge into total insolvency. Here are 15 celebrities you may not have realized went bankrupt.

15. Sinbad – Owed $11M

Everybody loves Sinbad — am I right? Well, maybe not anymore, but back in the day, he was one of the biggest (quite literally) funny men out there. If you’ve ever seen Jingle All the Way, then you know what a talent the man is. Alright, alright — I’m joking about that particular movie, but seriously, Sinbad was a big enough star in enough different vehicles to somehow have to file for bankruptcy to the tune of $11 million. You have to make an awful lot of money to owe that much money — that’s for damn sure. He first filed in 2009 and then again in 2013. He told Oprah in an interview, “I didn’t buy Bentleys. I didn’t live large. I invested in me. I invested in a lot of other people. I would not change it; I would not go back.” OK, that’s great Sinbad, but you might want to rethink that statement — you owe $11 million, guy!

14. Warren Sapp – Stop Buying Air Jordans!

He might have been an absolute beast on the field, but his personal life has been anything but easy. The NFL Hall of Famer has had a rough couple of years recently. Not only did he lose his high profile job as an analyst at the NFL Network — that’s what happens when you’re caught looking for h–kers at the Super Bowl — but he had to declare bankruptcy as well. I wonder if he’s upset that he lost his $540,000 a year TV gig? It turns out good old Warren, formerly known as “QBK” (Quarterback Killer) in his playing days, is also something of a financial killer, mostly based on bad purchases. In 2012, he owed $6.7 million to creditors. He had “assets” of $6.45 million. Unfortunately, a whole bunch of those assets was pair after pair of Air Jordans and tiger-skin rugs. Hmm, methinks Warren might have needed a little investment advice somewhere along the way.