2. Kevin Federline - Raw 2007
At least Khali was an actual wrestler though, which is more than can be said of Kevin Federlinewhose most notable prior experience with a ring was when he gave one to Britney in 2004. Of course, he also enjoyed a career as a rapper, dancer and actorapparently. Federline actually made multiple appearances with WWE in 2006, most of which involved altercations with none other than John Cena. Their exchanges culminated in a one-on-one match at the New Years Day edition of Monday Night Raw back in 2007. And Im sure you can see where this ones headed. Cena appeared to be in total control, before a brutal beatdown from an interfering Umaga left the champion on his back and down for the count. Needless to say, Federline returned to the fray once the Samoan Bulldozer had departed, covering the lifeless Cena to pick up the win. We often see celebrities involved in various segments when they guest star on Raw, but for them to actually pick up a winparticularly over someone of Cenas statusis an altogether different story. Admittedly K-Fed was said to have been very well-received by the guys backstage, so perhaps Im being a little too critical of him. Nonetheless, for the face of the company to lose to a non-wrestler makes this one of the most embarrassing WWE defeats of all time.