23. Charles Hamilton vs. Serius Jones
Winner: Serius Jones
Hot 97's long-running Who's Next showcase at SOB's is always guaranteed to have people talking about the next up-and-coming artists. However, on this night in 2009, all that talking came from the up-and-coming artist-and against battle rap royalty Serius Jones, who just stopped by to check out the show.
As Charles was ending the show, he hopped into the crowd with his microphone on and a J.Dilla instrumental playing in the background, and offered up the opportunity for aspiring rappers to spit. When Serius took the mic, he said "[This is] freestyle rambling; I'll show you how to do this, Charles Hamilton." That sparked something in Charles, who was headlining the show, after all, and resulted in a few rounds of back-and-forth rhymes.
Charles hit Serius about his failed label deal with Ludacris' DTP; Serius went after Charles' infatuation with the color pink: "This guy is a rookie; your clothes look like the inside of a pussy." Just as interesting: one of the aspiring MCs in the crowd that night, who went off when Charles passed the mic, was a then-unknown rapper named K.Dot, who grew up to become Kendrick Lamar. That night serves as a clear marker of time, where afterward we see Kendrick's career steeply ascend, and Charles' go into a severe nosedive.