Britney Spears’ three-year marriage to dancer and rapper Kevin Federline continues to be one of the most controversial periods in her life and career.
The former couple tied the knot in 2004 after only three months of dating and welcomed two children: Sean Preston Federline, born in 2005, and Jayden James Federline, born in 2006.
The timing of Federline’s whirlwind relationship with Spears ignited debate among her fans because he’d only recently split from Moesha star Shar Jackson while she was pregnant. (Kevin is a father of six: he shares daughter Kori and son Kaleb with Jackson as well as Sean and Jayden with Spears, plus daughters Jordan and Peyton with his second wife, Victoria Prince.)
Spears filed for divorce from Kevin in November 2006 and her subsequent breakdown led to her being placed under a conservatorship that lasted more than 13 years. Kevin later married his second wife, Prince, in 2013 and relocated their family to Hawaii.
Kevin opened up about his divorce from Spears in the 2025 memoir You Thought You Knew, which the singer’s rep dismissed as “sensationalism.” The dancer-turned-rapper exclusively told Us Weekly in October 2025 that he was “entitled” to share his “perspective” on their divorce.
Keep scrolling for more about Kevin’s ups and downs over the years.
Kevin Federline Gets His Start as a Backup DancerKevin Federline moved to Los Angeles in 1996 with dreams of being a dancer. He quickly lined up work as a backup dancer for Destiny’s Child, Pink and Michael Jackson, in addition to appearing in You Got Served and Will & Grace.
The Fresno, California, native even landed a job as a backup dancer in future wife Britney Spears’ ex-boyfriend Justin Timberlake’s 2002 “Like I Love You” music video.
Kevin Federline Welcomes 2 Children With Shar JacksonMoesha actress Shar Jackson started dating Kevin Federline in 2000. They welcomed two children during their relationship: daughter Kori Madison Federline, born in July 2002, and Kaleb Michael Jackson Federline, born in July 2004.
Kevin Federline Leaves Shar Jackson While She Is Pregnant With Their 2nd ChildBy the time Shar Jackson and Kevin Federline split in early 2004, she was pregnant with their second child, Kaleb. He started dating Britney Spears around that same time, leading to speculation over whether he’d cheated on Jackson.
In his 2025 memoir, You Thought You Knew, Kevin admitted he’d “handled the breakup with Shar poorly” because he wasn’t “honest or direct.” Federline confessed to telling a pregnant Jackson that he’d booked “a commercial shoot overseas” when he actually joined Spears in Europe for her Onyx Hotel Tour.
“I knew [the truth] would hurt her, and I didn’t want that,” he wrote. “If I could go back in time, I’d handle that whole thing differently. But life doesn’t work like that. We f*** up and we learn.”
Kevin eventually came clean to Jackson about secretly hooking up with Spears behind her back.
“I could hear the heartbreak in her voice, and the pain it caused,” he recalled. “She was angry. But under the anger was something deeper, a sadness I couldn’t undo.”
Kevin used his memoir as a chance to apologize to his and Jackson’s two children, writing, “I wasn’t the man I needed to be. I wasn’t the man I wanted to be. And for that, I am truly sorry.”
Britney Spears and Kevin Federline Get EngagedKevin Federline and his new girlfriend Britney Spears announced their engagement after only three months of dating. At the time, Spears admitted to People that the whirlwind nature of her engagement caught her off guard.
“Marrying Kevin was the last thing I was thinking about doing,” she said in July 2004. “But then I said, ‘You know what? This is my life and I don’t care what people think. I’m going to get married. I’m in love with him.’”
Earlier that year, Spears sought an annulment from her childhood sweetheart Jason Alexander only 55 hours after they got married in Las Vegas.
Britney Spears and Kevin Federline Wed 2 Months After Getting EngagedJive Records spokeswoman Sonia Muckle confirmed to the Associated Press in September 2004 that Britney Spears tied the knot with Kevin Federline in a non-denominational ceremony in Studio City, California.
Speaking to Entertainment Tonight in September 2025, Kevin claimed that he walked in on Spears on the phone with her ex-boyfriend Justin Timberlake on the eve of her wedding.
“I was like, ‘What’s wrong?’ I thought she was talking to her mom on the phone or something, and maybe she was having doubts,” Federline remembered. “And she told me she was on the phone with Justin.”
He went on, “I just kind of stepped back like, ‘Did I just hear you right? What the hell is going on?’ And I immediately was, ‘OK, we don’t have to do this.’ I didn’t care if we got married or not,” he said. “And she told me no and really was like, ‘I just wanted to make sure that everything is done. I want to make sure that I say my final piece.’ I’m like, ‘Damn. On the night before our wedding, this is what you decide to do?’”
Britney Spears and Kevin Federline Welcome Their 1st ChildOne year after getting married, Kevin Federline and Britney Spears confirmed the birth of their first child, son Sean Preston Federline, in September 2005.
“We are ecstatic to announce the birth of our son! Everyone is happy, healthy and doing wonderful. Thank you for all your love and well wishes,” they said in a statement posted on Spears’ website.
Sean Preston was born by a C-section at the UCLA Medical Center in Santa Monica, California.
Confusion Over Britney Spears and Kevin Federline’s 2nd Son’s NameMultiple media outlets reported on September 12, 2006, that Britney Spears and Kevin Federline welcomed their second son at Cedars-Sinai Medical Centre. The baby was delivered by a C-section at around 2 a.m. local time.
At the time, various outlets mistakenly reported that Spears and Kevin named their young son Sutton Pierce Federline. The new parents later clarified that Sean Preston’s baby brother was actually named Jayden James Federline.
Kevin Federline’s Debut Hip-Hop Album Is Savaged by CriticsKevin Federline made his debut as a recording artist with the release of his first studio album, Playing With Fire, in October 2006. He told Entertainment Weekly that the LP’s title was inspired by the trials and tribulations of his personal life.
“I feel like in my life, in the last couple of years, with everything that’s gone on, that’s how I feel — like I’m playing with fire,” he said. “[It could also mean] things I say on there are playing with fire, the press is toying with me, so they’re playing with fire — it goes all different ways.”
Both the album and its lead single, “PopoZão,” received brutal reviews from critics and fans alike. Playing With Fire became one of the worst-reviewed albums in the history of critical aggregator Metacritic.
Vibe panned the “constipated, region-nonspecific flow” that “overwhelms even the most flamboyant beats” while Slant called Playing With Fire “just as disposable and dumb as you’d expect.”
Federline responded to Playing with Fire’s critical drubbing by insisting that his music was not made for reviewers.
“This album is made for clubs,” Federline told the New York Daily News in October 2006. “When people are out, they want to hear people talk about drinking and smoking.”
Britney Spears Files for Divorce from Kevin Federline After 2 Years of MarriageBritney Spears filed for divorce from Kevin Federline on November 7, 2006, citing “irreconcilable differences” as the cause of the split. Multiple media outlets reported at the time that Spears broke the news to Kevin via a text message.
Kevin revealed in You Thought You Knew that he was promoting Playing With Fire when he was blindsided with news that Spears had already filed for divorce.
“I got to the studio, went through the usual motions with producers. I knew what to expect, another day answering the same questions, until a producer ambushed me — right before I went live on air — with: ‘How do you feel about Britney filing for divorce?’ My brain just … froze,” he admitted.
The rapper said that the way his divorce was handled was “humiliating, infuriating and devastating all at once.”
Kevin Federline Is Granted Sole Custody of His and Britney Spears’ SonsBritney Spears and Kevin Federline were involved in a protracted custody battle during their divorce. Spears was ultimately placed in a conservatorship by her father, Jamie Spears, in 2008 and would remain under her conservators’ legal control until 2021.
Kevin was awarded sole custody of his and Britney’s sons, Sean Preston and Jayden James, in January 2008.
Kevin Federline Marries His 2nd Wife Victoria PrinceKevin Federline started dating former volleyball player Victoria Prince in 2008. They welcomed their daughter Jordan Kay Federline on August 15, 2011, and wed at the Hard Rock Hotel in Las Vegas two years later.
Less than a year after tying the knot, Kevin and Prince welcomed their youngest daughter, Peyton Marie Federline, in April 2014. The family moved to Hawaii in 2023 when Prince accepted a job on the island.
That same year, Kevin hit back at reports that his family moved to Hawaii so his child support payments from Britney Spears would be extended. (The state allows for some child support to be extended to age 23 provided a child is enrolled in school.)
“A lot of people say a lot of stupid things,” he told PageSix.
Kevin Federline Wrote a Tell-All Memoir About His Marriage to Britney SpearsKevin Federline released his tell-all memoir, You Thought You Knew, in October 2025. The book includes Kevin’s concerns about the end of Spears’ conservatorship and her allegedly distant relationship with their sons.
Spears’ rep condemned Federline for allegedly trying to cash in on the singer’s name with a scandalous memoir.
“With news from Kevin’s book breaking, once again he and others are profiting off her, and sadly it comes after child support has ended with Kevin,” her spokesperson told Us Weekly in October 2025. “All she cares about are her kids, Sean Preston and Jayden James, and their well-being during this sensationalism.”
Kevin later defended himself in an exclusive interview with Us, insisting that he had the right to share his “perspective.”
“Money’s not the root of this thing,” he insisted. “I feel like, if she has the right to tell her story [with 2023’s The Woman in Me], why don’t I?”
Us Weekly reported that Kevin Federline was sued for an alleged unpaid credit card bill just two weeks before Britney Spears’ DUI arrest in March 2026. Us obtained court documents that showed that Bank of America sued Kevin over more than $12,000 on February 19, 2026, in Hawaii when he failed to make a payment.
Per TMZ, the Bank of America account was opened in December 2024, which was one month after Spears stopped paying Federline $20,000 a month in child support for their two sons.
Us reached out to Federline for comment.
