Britney Spears and Kevin Federline

Much like their wedding ceremony, which included groomsmen dressed in white tracksuits embroidered with the word “pimp,” Britney Spears and Kevin Federline’s courtship, marriage and eventual split was dripping with class at every turn. From a jilted mom-to-be to a bizarre reality show, these two really put the “fun” in “dysfunction.” Unfortunately, two adorable, innocent kids were caught in the crossfire.
Brit and K-Fed were just 22 and 25 when they met during a random night out at Hollywood hotspot Joseph’s in April 2004. Federline called it a “love-at-first-sight type deal,” which was inconvenient, to say the least, for his girlfriend at the time, Moesha star Shar Jackson, who was six months pregnant with their second child. Federline promptly dropped Jackson to follow Britney on her Onyx Hotel Tour. Within three months, the pair was engaged.
The proposal was truly a story for the grandkids. Spears mentioned the idea while the two were on a flight to New York. Federline shot her down, then immediately popped the question back to her. She, of course, accepted. Federline’s career as a back-up dancer wasn’t quite as lucrative as the multimillion-dollar empire that is Britney Spears, so she reportedly ended up forking over the cash for her own five-carat engagement ring. The puzzling proposal was an apt precursor to their entire nonsensical relationship.

Their whirlwind romance had all the trappings of a publicity stunt, but the pair actually ended up tying the knot on September 18, 2004. They had planned a ceremony for a month later, but with the media attention mounting, they surprised guests with an engagement party that ended up being a wedding. Not long after, Brit was preggers with the happy couple’s first child. On September 14, 2005, Britney gave birth to a boy, Sean Preston, via c-section. Within months, she was pregnant again.

Before Sean’s birth, the newlyweds decided they wanted their own reality show consisting of home videos from their courtship and wedding. After shopping the footage around to several networks to no avail, it was finally picked up by UPN. Britney and Kevin: Chaotic debuted in May 2005, and consisted of five episodes of incoherent dialogue and open discussions about their sex life. Surprisingly, it did not take.

In early 2006, their marriage started to get rocky. While Spears was pregnant with their second child, Federline was doing some creating of his own, investing his wife’s hard-earned money and fame into boosting his own music career. Tabloids started reporting that the couple was on the outs forcing a pregnant Britney to defend their union in a June Dateline interview with Matt Lauer, but succeeding only in proving that her conversion to full-blown trailer trash was complete.

On September 12, 2006, Britney gave birth to their second son, Jayden James. A month later, K-Fed birthed his first album, Playing with Fire. While Jayden turned out to be a beautiful baby, Fire was a hideous album that debut at number 151 and didn’t go anywhere from there. A week after its release, following an appearance on The Late Show, Brit filed for divorce from Federline and requested full custody of their children.

But by early 2007, Britney wasn’t making much of a case for herself as a mother. Following the death of a close aunt in January, she was spotted out partying regularly with Paris Hilton, often without underwear, she entered rehab only to leave after a day, shaved her head, attacked a paparazzo’s car with an umbrella and finally checked into rehab again.

After completing a 30-day program, the Spears-Federline marriage was officially dissolved in July 2007. A judge ordered her to undergo random drug and alcohol testing and granted temporary custody to the lesser evil that was Federline in August. In January 2008, Britney had an infamous complete mental breakdown and refused to hand her children over to her ex’s bodyguard. After holding the kids captive for several hours, police and paramedics wheeled her out of her home on a gurney and took her to the hospital where she was placed under involuntary psychiatric hold.

Following the incident, a judge granted conservatorship over her to her father, Jamie Spears, and Britney started to put her life back together. The former couple reached a custody agreement in July 2008 that reinstated Brit’s visitation rights, but Federline is still their primary guardian.

While K-Fed’s music career ended before it started, he went on to become extremely fat and star on Celebrity Fit Club. Britney, on the other hand, made a successful comeback thanks to the help of her family and her new, stable boyfriend Jason Trawick.

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