Sometimes it seems like fame, fortune and fantastic opportunities are wasted on celebrities. These spoiled bold-faced names have done their best to mess up their golden lives with bad attitudes, foolish choices and rude behavior. Read on to discover the people who have done so little with so very much.

10. Jessica Simpson

Even Jessica would probably admit that 2009 was not her year. On a concert tour, her weight and high-waisted jeans were ridiculed and the 29-year-old forgot the words to her own songs, prompting her to run off stage in tears in February. After being dumped by boyfriend Tony Romo in the summer and losing her dog, Daisy, a few weeks ago, Jessica appeared incoherent when talking about her own handbag line on QVC earlier this month. “You know more about my bags than I do,” she confessed on the air to host Patti Reilly.

9. Jon Gosselin

Jon Gosselin blew any hope of garnering public sympathy with his obnoxious behavior in the aftermath of his split from his wife and reality show co-star, Kate. He romanced several gullible younger women, took $180,000 from a joint bank account (which a judge ordered him to give back), and antagonized the producers of Jon & Kate Plus 8 so much that he is being sued for breach of contract. The delusional 33-year-old’s recent request for $12,000 to appear on a Florida radio station was met with laughter.

8. Amy Winehouse

This British soul singer’s drug fueled-rampages, rehab stays, turbulent marriage and scary skinny appearance made many forget how good her 2006 album Back To Black actually was. Amy hit rock bottom many times, including an incident in 2007 recounted by her ex-husband, Blake Fielder-Civil, when she nearly died from a seizure allegedly caused by heroin and crack use. Amy, now 26, claims she’s kicked the habit. She also recently had a boob job for prepare for her comeback.