Caged in 

Apparently winning an Oscar is not a Teflon-coated assurance of smooth sailing in the financial department. Despite countless motion pictures, Nicolas Cage, with his affable, Jimmy-Stewart-esque quality, could not shake off the aftermath of his relentless bad financial decisions. 

Cage sued his business manager, who countersued, according to The Street, saying, "...he told Cage to spend within his means but couldn't stop him from buying $33 million in homes, 22 cars, 47 pieces of artwork and a $276,000 skull of a Tarbosaurus." With a net worth of $18 million, you would think he'd be styling and profiling, but his spending may have him hawking his acting chops well into his golden years. 

The Beebs 

Social media comes just short of seizing up every time Justin Bieber tweets. Owning the top social rank on the Forbes 100 Most Powerful Celebrities list (2013), the Beebs is not just another egg-throwing, tantrum-having musician; he's also a savvy business lad. Or has some business-savvy lads or ladies advising him. At least for the time being… 

Either way, Enflick, Tinychat and Spotify are just a few of this crooner's startup investments to add to his recent earnings of $58 million, according to the Forbes list. He was #9 on the celebrity list and was ranked #4 in both TV/radio and press.