50 Cent – Vitamin Water, Estimated $100 Million

Rapper 50 Cent held some impressive endorsements deals during his career ($80 million from Reebok, $78 million from FRIGO Revolution Wear, etc.) but his biggest success story comes from Vitamin Water, a company that was sold to Coca Cola for $4.1 billion in 2007. Fifty’s contract not only included him fronting their Formula 50 line but also gave him a small percentage of the company itself, which earned him $100 million at the time of the sale. If it wasn’t due to some unfortunate business decisions, 50 Cent wouldn’t have to file for bankruptcy and still be one of the richest rappers in the world. Luckily, he found a better financial advisor and bounced back.