Hollywood’s Messiest Custody Battles: Brangelina, Britney Spears and Kevin Federline and More

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Hollywood's Messiest Custody Battles: Brangelina, Britney Spears and Kevin Federline and More

Battling for their babies. When there are children involved, divorce can get messy and turn exes into enemies. “We don’t see eye-to-eye. The friend that I was to Tameka, I don’t know that I could ever be again, because I really felt like we were friends. She made us enemies in a way that I never understood,” Usher said of his ex-wife Tameka Foster during a 2012 appearance on Oprah’s Next Chapter. The “Burn” singer broke down in tears on the witness stand in May 2012 amid his lengthy battle against Foster for custody of their two sons, Usher Jr. and Naviyd. During the trial, the stylist’s lawyer accused Usher of infidelity and neglecting his children. Usher later admitted to being unfaithful during the two-year marriage. After nearly three years of legal drama, a judge granted the Grammy Winner primary custody of the two boys in August 2012. Foster told Hollywood Unlocked that she hopes she and her ex-husband can repair their relationship one day. “He and I are definitely cordial and we coparent very well. Are we friends? I’d say no. I’d like for us to be friends. I miss my friend, he was my best friend before he was anything else. That’s my homie. We [are] cool,” she said during the 2021 interview. [jwplayer xKRkOVsV-zhNYySv2] While the “U Remind Me” singer eventually got a happy ending — he welcomed daughter Sovereign and son Sire with girlfriend Jenn Goicoechea in 2020 and 2021, respectively — other stars are still fighting for custody. Brad Pitt and Angelina Jolie have also been enmeshed in legal drama since the Maleficent star filed for divorce in September 2016. The exes — who are parents to Maddox, Pax, Zahara, Shiloh, Vivienne and Knox — are still working out a custody agreement of their minor children. In June 2022, a source told Us Weekly that Pitt had grown frustrated with his estranged wife’s legal tactics. “It’s very clear to him that Angie has gone out of her way to delay and stall the process,” the insider said. “All he can do is work with his legal team and file the paperwork whilst responding to her claims. Month after month goes by with one piece of red tape after another, endless jumping through hoops and bickering between their lawyers with no resolution.” The source told Us that the Fight Club actor was laying low to cope with the stress of the conflict. “Brad has been holed up at his place. He occasionally enjoys downtime at his art studio,” the insider revealed. Scroll through for a look at Hollywood’s messiest custody battles: [podcast_block]

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Olivia Wilde and Jason Sudeikis

Following Wilde and the Ted Lasso star’s November 2020 split, Sudeikis served his former partner custody papers regarding their two children, Otis and Daisy, while she was on stage at CinemaCon in April 2022. During her Don’t Worry Darling presentation, Wilde was handed a manila envelope that was labeled “personal and confidential.”

While a source told Us at the time that Sudeikis “would never condone” Wilde being served in “such an inappropriate manner,” she later alleged he was attempting to humiliate her.

Wilde filed court documents of her own that August, which allegedly slammed Sudeikis for trying to “embarrass” and “threaten” her over its public delivery. The paperwork, obtained by the Daily Mail, noted that the exes initially agreed that Otis and Daisy would complete the school year in Los Angeles while the Saturday Night Live alum films Ted Lasso season 3 in London.

“Jason’s actions were clearly intended to threaten me and catch me off guard. He could have served me discreetly, but instead, he chose to serve me in the most aggressive manner possible,” Wilde claimed in her filing. “The fact that Jason would embarrass me professionally and put our personal conflict on public display in this manner is extremely contrary to our children’s best interests. Since Jason has made it clear that we will not be able to work this out for our children’s sake outside of the court system, I filed a petition for custody in Los Angeles.”

Sudeikis responded to Wilde’s filing and noted that he did not want to serve his ex at the “home of Olivia’s current partner,” referring to Harry Styles — whom Wilde began dating in January 2021 — because their kids might be there. He also did not want her to be served at Otis and Daisy’s school because other “parents might be present.”

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Britney Spears and Kevin Federline

The “Toxic” singer shares two sons with her ex-husband: Sean, born in 2005, and Jayden, born in 2006.

When Spears filed for divorce in November 2006, she asked for full custody of her boys, with Federline to receive “reasonable visitation rights.” When the divorce was finalized the following year, the pair agreed to equal custody.

However, after the Crossroads actress was placed on a 5150 psychiatric hold in January 2008, the “PopoZão” singer was awarded sole custody of his sons. That June, Spears was granted two visits and one overnight a week.

Federline requested an increase in child support payments in February 2018. “Britney is extremely agitated and extremely concerned that Kevin is going to no longer allow her to see their children because he has sole custody as retribution for not agreeing to the $40,000 in child support payment, which would be a $20,000 increase from what he is getting now,” a source told Us that May.

The legal battle came to an end in September 2018 when Spears agreed to increase her payments to around $35,000 a month. The duo made a change to their custody agreement in August 2019, giving the "Circus" singer 30 percent custodial rights.

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Brad Pitt and Angelina Jolie

The Mr. and Mrs. Smith costars are still enmeshed in a custody battle, years after Jolie filed for divorce in 2016. In April 2022, a source exclusively revealed to Us that the Ad Astra actor had been telling friends he feared his ex-wife would “never agree to joint custody and is going to run out the clock until the kids are 18.”

The former couple share six children together, four of whom are minors: Maddox, born in 2001, Pax, born in 2003, Sahara, born in 2005, Shiloh, born in 2006, and Vivienne and Knox, born in 2008.

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Halle Berry and Gabriel Aubry

The Catwoman star and her ex-partner's custody battle for their daughter, Nahla, centered around Berry's desire to move to France with her then-fiancé, Olivier Martinez. Things got ugly when Aubry got into a physical fight with Martinez on Thanksgiving Day in 2012. Neither party was criminally charged for the incident.

One week later, the exes reached a custody agreement, with a judge denying Berry's request to permanently relocate with Nahla. The X-Men actress welcomed a son, Maceo, with Martinez in 2008. The duo separated in 2015.

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Ciara and Future

In 2016, the “Goodies” singer sued her rapper ex for defamation. The $15 million lawsuit focused on interviews and a Twitter rant in which the Georgia native spoke ill of Ciara and her then-boyfriend, Russell Wilson.

The Game actress dropped the suit against Future the following year and agreed to joint custody of their son, Future Jr., after previously requesting sole custody. Ciara and Wilson wed in 2016 and welcomed daughter Siena and son Win in 2017 and 2020, respectively.

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Usher and Tameka Foster

The R&B singer won primary custody of his sons Usher Jr. and Naviyd in August 2012 after a contentious custody battle that lasted over three years. During the trial, Foster's lawyer claimed that Usher had neglected his children. “It’s a relief it’s over,” an insider told Us at the time. “An independent party looked at the evidence and did the right thing.”

The personal stylist requested an emergency hearing in August 2013 after Usher Jr. was injured while swimming at his father's house. She requested temporary custody of her and Usher’s sons, but a judge ruled in favor of the “My Boo” singer retaining primary custody.

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Bethenny Frankel and Jason Hoppy

The exes, who wed in 2010 and announced their split in 2012, both sought primary custody of their daughter, Bryn, when they filed paperwork in 2013. Although they reached a joint custody agreement the following year, Frankel went on to sue Hoppy for full custody in 2019.

The Real Housewives of New York star’s ex was arrested in January 2017 after he allegedly threatened her during an unplanned visit to Bryn’s school. Hoppy was issued a six-month stay away order from Frankel that October. The following year, his lawyer Robert Wallack argued that the death of Frankel’s on-off boyfriend Dennis Shields reflected poorly on the reality star’s ability to parent.

“It was reported that he [Shields] died of an Oxycodone overdose,” Wallack said in court. “Our concern is while his death is very sad, this raises serious concerns about Ms. Frankel’s parental judgment.”

The Skinnygirl founder was awarded full legal custody of Bryn in 2020. In December 2021, a judge ruled that the Skinnygirl founder no longer had to pay her ex-husband child support as Bryn was living primarily at her house.

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Sherri Shepherd and Lamar Sally

The 30 Rock alum filed for divorce in May 2014 after marrying Sally in 2011. Months after their split, the couple welcomed a son, Lamar Jr., via surrogate in August 2014. Shepherd has no biological relationship to the child and initially sought to have her name removed from his birth certificate.

In November 2015, a judge declared that the Precious actress was legally responsible for Lamar Jr. and therefore had to continue paying child support to her ex-husband.

Sally, who has raised Lamar Jr., as a single father, sought increased child support payments in December 2016. A judge denied the request.