Year: 2007

50's involvement in Vitamin Water, as an investor and not just a spokesperson, was highly publicized. While he may not have made the $400 million that was initially reported, it's safe to say he walked away with a pretty penny (Forbes estimates it at closer to a measly $100 million) and completely redefined the rap artist/advertiser relationship. For this goofy commercial for the product, 50 conducts a symphony orchestra that performs "In Da Club" and gets DJ Whoo Kid a primetime cameo. It's the classic fish-out-of-water cliché of the rap commercial. To ad execs there's nothing funnier than a rapper in a room full of stuffy squares or white old men using phrases like "true OG." To 50 nothing is funnier than making tons of money off, er, with old white men.