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Britney Spears and Kevin Federline's 9 most 'chaotic' moments as a couple

Suzy Byrne
Editor, Yahoo Entertainment
Britney Spears and Kevin Federline are battling it out over child support, but their relationship has always been chaotic. (Photo: Getty Images)

Britney Spears and Kevin Federline’s brief romance was so chaotic that they turned it into a reality series with the same name. From the very start — hooking up when he was expecting a baby with Shar Jackson — it was dramatic and continued that way through when she announced that she was divorcing him, which he learned via a text message to his BlackBerry. (Remember those?) But the drama didn’t stop there — remember her shaved head?

While Britney and “Fed-Ex” would go on to stand cordially a few feet apart at their sons’ sporting events after they split — and both moved on romantically, a few times over — they still aren’t in a happy place today. Kevin, who’s remarried and a father of six, wants more child support. (Monthly checks for $20,000 aren’t enough to keep them living at the standard to which they’ve grown accustomed with Mom, claims Kevin. What — you thought “PopoZão” royalties would cover his bills?) Britney, 36, has been saying “Hell, no, y’all” via her conservator dad, Jamie Spears, who thinks that Kevin, 40, isn’t spending his checks properly (and is maybe spending them on the rest of his kids).

Seeing the pair’s names in the same sentence again so many times with this new battle over child support, we look back at the most “chaotic” moments from their relationship. So follow along — no Cheetos, Slurpees, or Von Dutch hats required…

1. Their hookup drama. The Louisiana-raised “Toxic” singer first briefly met Kevin, from Fresno, Calif., when he was a backup dancer for the boy group LFO, which was touring with the pop princess in 2000. They were reintroduced while clubbin’ in L.A. in April 2004, and Britney, then 22, and Kevin, 26, were instantly smitten. The glitch? K-Fed, as he was quickly dubbed, was expecting a second child with his on-again, off-again girlfriend, Moesha actress Shar Jackson. The “other woman” headlines began immediately (Jackson told People magazine, “It wasn’t like just breaking up a relationship. It was like breaking up a family”), but Britney didn’t seem fazed. She openly flaunted her new relationship — memorably posing for paparazzi pics with her new beau at a Santa Monica, Calif., beach, after a stop at Subway for lunch — and even publicly played mom to Kevin’s daughter, Kori. Awkward.

When Brit and Kevin started dating in April 2004, they gamely posed for paparazzi at a Santa Monica beach. (Photo: Splash News)

2. Their quickie engagement. In January 2004, Britney briefly married her childhood chum Jason Alexander, but the union was annulled 55 hours later. (If there were a gif of Jamie Spears wiping his brow, we’d put it here.) By June of that year, though, Britney — who was quickly feeling marriage-minded — invited Kevin on tour with her through Europe. It was on that tour that they became engaged — after modern woman Britney popped the question. The actual proposal took place at 10,000 feet as they traveled from New York to Ireland. Brit asking Kevin to marry her made sense, considering he couldn’t afford a ring; he didn’t have an income and had a few mouths to feed back home. So the same summer the star was famously photographed walking barefoot out of a gas station bathroom, she also started sporting a 5-carat rock on two platinum, diamond-encrusted bands.

Britney and Kevin became engaged in the air — then shared the deets with People magazine. (Photo: People magazine via Splash News)

3. A surprise wedding. Thirty or so of their closest family and friends were invited to what the people thought was an engagement party at the Studio City home of her wedding planner on Sept. 18, 2004. However — surprise! — it was actually a wedding. Brit-Brit donned a $26,000 strapless silk gown and some Madonna-like lace gloves to walk down the aisle; K-Fed changed out of the white tank top that he had worn to greet guests into a suit for the “I do’s.” After the reception, during which Kevin removed Britney’s garter belt with his teeth while his mom cheered him on (yeehaw!), guests changed into sweatsuits embroidered with “pimps” and “maids” (Britney’s said “Mrs. Federline,” while Kevin’s said “The Pimp”) and went out clubbin’ in L.A. The couple’s marriage wasn’t legalized until Oct. 6, after their prenup was finalized.

At their wedding reception, Kevin removed Britney’s garter belt with his teeth while his mom cheered him on. (Photo: YouTube)
After their wedding, they went clubbing in matching sweatsuits: “Mrs. Federline” for her and “The Pimp” for him. (Photo: Splash News)

4. Their crazytown reality show. Perhaps the greatest gift that Britney and Kevin shared with the world was their reality show, Britney & Kevin: Chaotic, which aired from May 17 to June 14, 2005, on the defunct channel UPN. Through their own shaky home videos, they treated viewers to an intimate look at their courtship and wedding. And by intimate we mean we listened to them talk about their sex life — a lot. Beyond that, they drank, smoked, swapped spit, and … talked about farts. Another memorable moment was when they recorded themselves racing through her fancy European hotel suite and sliding on their bellies across a banquet table over and over (see below at 1:18 mark). It proved that there truly is a lid for every pot.

5. The back-to-back babies. Kevin’s second child with Shar, a son, Kaleb, was born in July 2004, but by 2005 he had already started his second family with Brit, who embraced belly-baring maternity wear. Less than a year after marrying, they welcomed their first son, Sean Preston, on Sept. 14. Less than a year after that, they welcomed another son, Jayden James, on Sept. 12. But by that point, their marriage was already in big trouble.

Mama-to-be Britney Spears with Kevin Federline at the Charlie and the Chocolate Factory premiere in 2005. (Photo: Jeffrey Mayer/WireImage)

6. Major parenting woes. The young couple — specifically Britney, because by then they were often apart, with Kevin pursuing a rap career (remember “PopoZão”?), golfing, clubbing, or driving his fancy new fleet of cars — were the target of much criticism regarding their parenting skills in 2006. Britney was famously photographed driving with baby Sean on her lap, instead of — ya know — being strapped safely in a car seat. (“We’re country,” she famously told Matt Lauer.) A sheriff’s deputy went to their Malibu, Calif., home to investigate after Sean fell out of a broken high chair. And while visiting New York City, Britney had Sean in one arm and a glass in the other when she nearly dropped the tot on a cobblestone street. Photographers captured the moment of the baby’s head being jerked backward while she kept the glass steady, not spilling a drop. Nobody was seriously hurt, other than Britney’s feelings over the mean headlines. However, Britney and Kevin laughed off the criticism in a skit at the 2006 MTV Video Music Awards in which they joked about not knowing where Sean was.

Their children arrived within a year of one another — and the couple were criticized for their parenting skills. (Getty Images/Splash News)

7. Their text-message breakup. Tears were a theme in 2006. By the fall, Kevin was often off partying with his boyz in Las Vegas, and Britney, now juggling two young children, looked miserable every time they were photographed together. However, on Nov. 6 — just over a month after having Jayden — she looked incredible in an appearance on Late Show With David Letterman. The world was used to seeing her pregnant for the previous two years, but she looked red-hot in a tiny black dress and a blond wig. Something was up, though. She went right from the Ed Sullivan Theater to nearby Sony Studios, where she faxed her signature to the Los Angeles lawyers handling her divorce. The next day, divorce papers were filed — and Kevin was supposedly blindsided by her decision. In Canada promoting his new album, he famously found out that he was being dumped via a text message to his BlackBerry. Even worse, the press dubbed him “Fed-Ex.”

Britney filed for divorce from Kevin — and he found out via text message. (Photo: Splash News)

8. A wicked custody battle. Their divorce was a vicious one, with the pair immediately fighting over their children, and Britney became the biggest loser. The pop singer took to partying — sometimes with Paris Hilton, sometimes without her undies — and slipped into a downward spiral. Her parents forced her into rehab — she stayed one day — and when she was out, she bizarrely wandered into Esther’s Haircutting Studio in Tarzana, Calif., and asked the owner to shave her head bald. When the woman refused, Brit, who may have been trying to evade a drug test, picked up the clippers and did it herself. She went to a second rehab facility months later, but that didn’t slow down her partying or bizarre behavior. The divorce was finalized in July 2007, but the custody arrangement wasn’t. After she was charged in a hit and run, she was banned from driving with her children but did it anyway. She also took her children out of state without the court’s permission, and was photographed taking the toddlers out to restaurants late at night. So by October, a judge temporarily granted Kevin primary custody of their kids.

After her split with Kevin, Britney shaved her head bald — and ended up in rehab multiple times. (Photo: Splash News)

9. Her epic meltdown. The drama continued in a big way. In addition to new driving charges, skipping court-ordered drug tests, and refusing to be deposed in her custody battle, one night in January 2008 Britney refused to turn over the children to Kevin after a visitation at her home, locking herself in a room with Jayden. Her court-appointed child monitor called police, who claimed she was under the influence of an unnamed substance and forcibly removed Britney from her home. She was taken to a hospital and placed on a 72-hour lockdown for mental evaluation — with photos of her on a gurney being loaded into an ambulance plastered everywhere. A month after Britney’s hospitalization, her father, Jamie, petitioned for conservatorship over her affairs. Over time, he helped her turn things around, including reaching an amicable joint custody arrangement with Kevin, with whom Jamie and his wife, Lynne, maintained a friendly relationship. Britney and Kevin also went from cutthroat to cordial.

Britney was forcibly removed from her home and hospitalized after refusing to turn over the children to Kevin per their custody agreement. (Photo: Splash News)

In 2013, Kevin — who went on to appear on Celebrity Fit Club and a couple of episodes of One Tree Hill but otherwise is DJ’ing now and then — married his longtime girlfriend, special education teacher Victoria Prince, with whom he has two children. Britney’s relationships have remained more dramatic. After dating paparazzo Adnan Ghalib (no surprise, it didn’t end well), she became engaged to her manager Jason Trawick (ditto) and ended a relationship with law-firm researcher David Lucado after he cheated on her with a porn star (another fiasco). Her time with Charlie Ebersol seemed relatively drama-free, and so does her current relationship with model Sam Asghari, whom she met on the set of her “Slumber Party” music video.

In 2013, things between Britney and Kevin were cordial enough that they could be near each other at their sons’ sporting events but were never alone together. Here they are, along with Jamie Spears, left, and Britney’s ex-boyfriend David Lucado, second from right. (Photo: Splash News)

As for the pair’s sons, Preston and Jayden, despite this ongoing mess, they seem happy and look healthy in the glimpses we get on mama Brit’s Instagram.

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