Looking Back at 5 of Britney Spears' Biggest Controversies Over The Years

Looking Back at 5 of Britney Spears' Biggest Controversies as She Turns 42 

Britney Spears celebrated her 42nd birthday last week by embracing "singlehood" and the success of her hit memoir, The Woman in Me. The Sometimes hitmaker is battling custodial issues with her ex-Kevin Federline and preparing for divorce from her estranged husband, Sam Asghari. With her controversial online dancing posts and emotional outbursts, her past years have been tumultuous. As per The UK Mirror reports, overcoming her thirteen-year-long conservatorship and gaining her financial freedom back was the main highlight before turning 42. Here are some of the most controversial episodes of her life as she turns a year older.

1. Sam Asghari Accuses Britney of Cheating and Files for Divorce

Sam Asghari and Spears became romantically involved while working together on the Slumber Party music video shoot. The couple got engaged in September 2021 and got married in an intimate ceremony the following June in Los Angeles. As People reports, in March, both were spotted sans the wedding ring, with marital discord doing the rounds. On August 17th, the fitness model issued a formal statement on social media announcing the couple's decision to split, citing "irreconcilable differences." Asghari accused the Toxic hitmaker of making nude videos with a male staffer and also caught them in a compromising position as per a secret found footage, reports TMZ. Asghari demanded spousal support and legal fees after filing for divorce. However, as per US Weekly reports, an unbreakable prenuptial agreement that firmly protects the singer's estimated $60 million wealth was signed by Spears and Asghari. According to the source, the prenuptial agreement specifies that Asghari will receive "$1 million per every two years" of their marriage, with a ceiling of $10 million after 15 years. Along with giving up any rights to Spears' music library, the model also agreed to transfer ownership of their shared property into an LLC rather than having his name on the title.

2. 13-year-old Conservatorship 

Using a type of legal guardianship known as a conservatorship, Jamie Spears and others have been in charge of the Circus songstress's personal affairs and finances for the past 13 years. Jamie's lawyers said the conservatorship was "necessary to protect Britney in every sense of the word." They said, "Her life was in shambles, and she was in physical, emotional, mental, and financial distress." Two conservatorships were established for Britney: one for her personal affairs and estate, and the other for her business dealings. Jamie oversaw all aspects but resigned in 2019 as his daughter's personal conservator due to health concerns. A court-appointed caregiver took over in his place. In September 2021, Britney's father was removed from his role. She and her attorney selected an accountant to take his position. "This conservatorship is doing me way more harm than good," she said. "I deserve to have a life." According to the singer's attorney, her father had been "reaping millions of dollars from his daughter's estate" and engaging in financial malfeasance. On November 12, 2021, her conservatorship was terminated by Judge Penny.

3. Justin Timberlake Affair 

Spears and Timberlake dated from 1999 until 2002. The Baby One More Time songstress revealed the bombshell details about their relationship in her tell-all memoir, The Woman in Me. Timberlake cheated on Spears the entire time they were dating, according to the book. “There were a couple of times during our relationship when I knew Justin had cheated on me. Especially because I was so infatuated and so in love, I let it go, even though the tabloids seemed determined to rub my face in it,” she recalled. “When NSYNC went to London in 2000, photographers caught him with one of the girls from All Saints in a car. But I never said anything. At the time, we’d only been together for a year.” While Spears was filming her music video for Overprotected (Darkchild Remix), Timberlake allegedly ended their three-year-old relationship with a simple text saying, "It's over!!" “After seeing the message as I sat in my trailer in between takes, I had to go back out and dance,” Spears wrote, reports E! News. “For as much as Justin hurt me, there was a huge foundation of love, and when he left me, I was devastated. When I say devastated, I mean I could barely speak for months. Whenever anyone asked me about him, all I could do was cry. I don’t know if I was clinically in shock, but it felt that way.” Timberlake gifted her a framed break-up letter later, which Spears still keeps under her bed. "I can’t breathe without you.’ Those are the last words in it,” she wrote.

4. Timberlake Played Guitar While Spears Had an Abortion 

As per Harper's Bazaar article, Spears' shocking memoir stated that Timberlake coaxed her to get an abortion. “It was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated,” she wrote in an excerpt published by People. “But Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young.” “It was important that no one find out about the pregnancy or the abortion, which meant doing everything at home,” the Everytime songstress wrote. Only Spears, Timberlake, and Culotta knew about the abortion, which was carried out by taking "the little pills." "At some point, he thought maybe music would help, so he got his guitar, and he lay there with me, strumming it. … Still, they didn’t take me to the hospital,” Spears wrote in her memoir.

5. Volatile Relationship with Ex-Husband 

Spears and Federline first met in 2004 at a club in Hollywood; the couple tied the knot the same year, in September, after a whirlwind romance. “It is great that this (wedding) has happened because it has made me realize that I am growing up, becoming a woman, and things just need to be different,” Spears told at the time. “I feel like it’s a beginning.” The couple welcomed their first son, Sean Preston Federline, in 2005 and their second son, Jayden James Federline, in 2006. The Toxic Pony songstress filed for divorce from her husband soon after giving birth to her second child, citing "irreconcilable differences." The couple finalized their divorce in 2007, and Federline has kept demanding extra child support since then. By 2019, Spears was granted 30% of unsupervised custodial rights to her children, whereas Federline had 70%. In 2022, they engaged in a series of online wars of words: “It saddens me to hear that my ex-husband has decided to discuss the relationship between me and my children ...” Spears wrote on Instagram. “As we all know, raising teenage boys is never easy for anyone." In 2023, Federline shifted to Hawaii with their two sons and still expects to get more child support.