Winner: 40 Cal
Year: 2004

Dipset's 40 Cal. apparently had no idea who he was battling with. No, really: in a video commentary, 40 Cal. says he didn't know Sam Scarfo's name until midway through this Fight Klub appearance. Still, though generic, his punchlines packed wallops, saying of Scarfo: "His heat only go off, 'cause he don't pay his gas bill." (Also: "I'll put you in an all-white cast like Seinfeld.")

Scarfo, in their rematch, would say, "It's a shame your team lame, and your future rides on Jim Jones," but he just didn't come with anything touching 40 Cal. in this first battle, and 40 Cal. walked away with the crown.

Don't sleep, though. Scarfo would go on to win their televised rematch, telling an interviewer afterwards, "They say I won the most money at Fight Klub in the shortest amount of time in history." Unfortunately, Fight Klub would spell the end of his riches and fame. Shortly after this match-up, Sam Scarfo became the first solo artist signed to Def Jam under Jay-Z where he'd be buried in obscurity beneath Ne-Yo, Rihanna and somewhere behind Teairra Mari. It's a shame his future was riding on a major label.