Date: Winter 1990

The Moment: Filmed on the campus of the University of Tennesee over three days, MC Hammer's biggest endorsement started to air around Thanksgiving of 1990. It was an ad for Pepsi—the extended version of which ran a full minute—in which the rapper starts singing "Feelings" after having his Pepsi switched out for Coca-Cola. Given a Pepsi by an audience member, Hammer returns to rapping and dancing, and being MC Hammer, in 1990. 

The Impact: The endorsement was one of several at the time that added to Hammer's bankability, and was one of the largest rapper-endorsement deals in history, at that point. Sure, it did wonders for Pepsi, but it inflated Hammer's bank account to such an absurd degree that he didn't know what to do with it. Literally, Hammer (officially) went broke in 1997, crying poor with $13.7 million in debt, and only $9.6 million in assets to cover it.

The Upshot: While debates about Coke vs. Pepsi rage on to this day, another one runs a little more under the cultural radar: whether or not criticism of Hammer for taking the Pepsi endorsement money (and the sellout label) was fair. For one, deals like Hammer's are de rigueur for rappers in 2013. So what's so wrong with a little paper? Purists argue it destroys any semblance of artistic intent or merit. Whatever side you're on, know this: Hammer seems to be living a satisfied life without all the cash, but it came at the price of hip-hop credibility.