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#2: Kevin Federline
For you young whippersnappers who may not know who Kevin Federline is, the California rapper has had a successful music career, but is perhaps best known for his marriage to Britney Spears from 2004-2007.
After splitting with the popstar, K-Fed turned his attention to wrestling, appearing on Monday Night RAW on multiple occasions and eventually finding himself at odds with then-WWE Champion and fellow rapper John Cena
After costing Cena the World Heavyweight Championship at Cyber Sunday 2006, Federline and Cena squared off on the January 1, 2007 edition of RAW, in a match many assumed would be an easy win for the Chaingang leader.
However, with A LOT of help from Umaga and Johnny Nitro, K-Fed would shock the world, getting one of the biggest upsets in RAW history, though did receive an AA by the end of the night.
