#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
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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.