Winner: Serius Jones
Year: 2005

As if torn from the pages of someone's 106 & Park fan fiction, Freestyle Friday champs Serius Jones and Jin Tha MC finally faced one another for Fight Klub and MTV2's cameras in 2005. It got ugly quick, with Serius ripping apart Jin's go-to playbook in his opening lines: "I done peeped your whole rhyming game, it's kinda lame/All you do is look around, find a celebrity and start dropping names/Then, with a weak crowd, you throw old punchlines in the mix and call it a freestyle." More notably, Serius says, "Ain't there two billion people in China? How you ain't go platinum over there?" And it only gets more racist from there!

It's a fairly one-sided fight, because Jin's race-baiting isn't as appealing to the crowd as Serius'. That being said, Jin doesn't back down, nearly snatching the prize money away with the lines, "I ain't surprised that you came with your mans/But y'all like D-12, no one knows the name of your band!"