Professional wrestling is a strange business. We all know that it not only has predetermined winners and losers, but we accept wild storylines and segments that are not at all plausible. Where else could a companyâs owner or creative head book themselves to be the world champion, like Vince McMahon in WWE and Vince Russo in WCW?
Thatâs how, in 2007, John Cena had one of his lowest moments. He was the face of the company, but that didnât stop Vince McMahon from booking him to lose to a D-list celebrity named Kevin Federline. If youâre not of a certain age, you might be wondering just who the heck Kevin Federline is. His claim to fame for fifteen minutes is that he was married to Britney Spears. He was highly made fun of in pop culture, but for one night he could claim that he beat the GOAT of WWE.

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Kevin Federline Was Married To Britney Spears
Federline Also Released A Rap Album
- Kevin Federline was a backup dancer.
- Federline married Britney Spears in 2004.
- Spears filed for divorce in late 2006.
Kevin Federline was a high school dropout from California who had a dream to be a dancer. His dedication led to him being a backup dancer for huge names like Michael Jackson and Justin Timberlake. He could also be seen dancing in music videos for Timberlake and Pink. So you have to give him credit for being a successful person before he ever met Britney Spears. In 2004, he met Spears, who was one of the biggest pop stars on the planet. After just a few months of dating, the two got engaged, and a few months after that, in September 2004, they were married.
The public was not a fan of Kevin Federline, whose look and attitude rubbed people the wrong way. Britney Spears was seen as one of the most beautiful and famous women on the planet and this was the guy she chose to marry? In November 2006, Spears filed for divorce. This meant Kevin Federlineâs fifteen minutes were about up, but a highly publicized divorce meant he could squeeze every last drop out of his celebrity status. This led him to WWE.

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Kevin Federline Beat John Cena On An Episode Of WWE Raw
John Cena Was Attacked By Umaga During The Match
- Johnny Nitro and Melina advertised the arrival of a mystery A-List celebrity.
- Kevin Federline was on WWE Raw to promote his rap album.
- Federline tried to do a Master Lock Challenge with Cena.
Kevin Federline had some minor acting gigs during his time with Spears, but he also had a music career, releasing a much-ridiculed rap album in 2006. Another white rapper out there who was often criticized was WWE wrestler John Cena. Federline showed up on WWE TV in the fall of 2006 to promote his album on Raw, a moment fans couldnât have cared less about. What was worse is that he was a surprise guest, having been built up to be an A-List mystery appearance by Johnny Nitro and Melina, only for the ex of Britney Spears to walk out. Talk about a letdown. Federline cut a heel promo, which was thankfully cut short by a rap promo from an interrupting John Cena, who verbally destroyed the ârapperâ before getting in the ring and destroying him physically with an Attitude Adjustment.
That could have been the end of it, but Kevin Federline returned to Raw the next week, now with Booker T (during his heel King Booker days) by his side singing his praises. This led to another Cena promo, but later in the night, in the ultimate act of disrespect, Kevin Federline slapped the WWE Champion. The bad times continued at the Cyber Sunday PPV when, during a champions match with King Booker and the Big Show, Federline hit Cena in the head with a belt, costing him the match. This led to him challenging Cena in a singles match to be held on the first Raw of 2007. What a bad way to start the year!
John Cena vs. Kevin Federline was a no DQ match, with Federline having Johnny Nitro in his corner. This meant there would surely be outside shenanigans, which was necessary since Federline wasnât a trained wrestler. To really play into how much of a heel he was, Federline even put on headgear like this was a boxing match. He then challenged Cena to a Master Lock challenge which, of course, didnât go as well as it did for Chris Masters. It then turned into a traditional match of sorts, but with Federline getting in a low blow. Thankfully, the mess was put out of its misery when Cenaâs rival, Umaga, came down to the ring and attacked the champ. With Cena now unconscious, Kevin Federline pinned him and got the win.

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How Did John Cena Handle The Loss Backstage?
WWE Hoped To Get Britney Spears To Appear As Well
- John Cena vs. Kevin Federline wasnât a WWE Championship match.
- Cena realized that losing to Federline was just part of business.
- Michael Hayes wanted Britney Spears to sing a song on WWE TV.
If this match had been for the WWE Championship, the outcome would have topped even the atrocity that was David Arquette as the WCW World Heavyweight Champion. As it was, Federline disappeared after the champ came back later in the night to deliver an FU to the man who beat him, then Cena moved on to Umaga unscathed. On his Oh You Didnât Know podcast, Road Dogg spoke about how John Cena handled the booking decision, saying:
âItâs business. He was asked to do it. It mightâve been his idea because thatâs how John Cena works. He thinks about the bigger picture, he has a vision. Look, mission accomplished.â (h/t 411Mania)
As strange as it all was, on his Something To Wrestle podcast, Bruce Prichard revealed that Michael Hayes hoped to take it even further with a Britney Spears concert at a WWE show.
âYou go with the Michael Hayes philosophy of âDo you think Britney would come to see Kevin Federline with John Cena? We could get Britney and I can ask her if she can sing a song. That would be good for pay-per-view. Yeah. He just assumed she would travel with him and we could get Britney to do something.â (h/t Fightful)
Say what you will about John Cena during this time in WWE, but the fact that he agreed to lose to Kevin Federline as a way to put on an exciting show proves that he would do whatever it takes to entertain the fans. Itâs probably one more reason why his character finally turned heel though.