Another year, another round of celebrity legal battles reminding us that even in 2025, the toxicity and criminal activity in Hollywood runs deep.
The cracks have been showing for years, if not decades; between major filmmaker Harvey Weinstein, convicted of rape, and beloved Princess of Pop, Britney Spears, who revealed that she had been practically forced to perform at gunpoint, the industry’s reckoning has been a long time coming. And although we are still very far away, important progress has been made this year.
If you thought 2024 was chaotic, 2025 showed that Hollywood’s legal storm is just beginning.
1. Sean ‘Diddy’ Combs’ Reckoning
A year after his arrest in September 2024, Sean “Diddy” Combs faced the biggest reckoning of his career: a federal criminal trial that lasted nearly two months in the summer of 2025. After weighing five felony charges, the court sentenced Combs to 50 months in prison (4 years) with a fine of $500,000. It could have been much worse; He avoided a possible life sentence after being acquitted of the two main charges: sex trafficking and conspiracy to racketeering.
The trial, which was not televised, began May 12 under Judge Arun Subramanian in a Manhattan courtroom with a 12-person New York jury of eight men and four women. From day one, Combs’ defense rested on a technical distinction critical to his case. “Domestic violence is not sex trafficking,” they argued in their opening statements, framing the prosecution’s narrative as an overreach rather than a federal crime (bbc).
The prosecution’s star witness was Combs’ ex-girlfriend, Cassandra “Cassie” Ventura, who signed to Combs’ Bad Boy Records in 2005 at age 19. Her 2023 sexual assault lawsuit, settled within 24 hours for $20 million, triggered a wave of more than 70 civil lawsuits against Combs and helped set the stage for the federal investigation. On the stand for four days, Cassie described being assaulted by Combs while trying to flee one of his alleged “freak-offs” in 2016, a moment that was caught on camera and leaked by cnn months before Combs’ arrest.
Combs’ team did not call defense witnesses nor did Combs take the stand. Instead, they opted for aggressive interrogations. Legal analyst Mitchell Epner noted that the strategy indicated confidence: that the prosecution’s witnesses “made our case” and that the defense did not need to present additional testimony to raise reasonable doubt (USA today).
Several high-profile figures participated in the process. Kid Cudi testified that his car was deliberately blown up during the period in which he briefly dated Cassie. Other celebrities, such as Usher and Justin Bieber, emerged in online conspiracy theories. Kanye West even showed up at the courthouse one day to support Combs. Suge Knight, founder of Death Row Records, publicly defended Combs from prison despite their infamous rivalry. Meanwhile, 50 Cent’s most-watched Netflix documentary about Combs intensified public scrutiny with footage and allegations dating back to the 1990s.
After six weeks, the jury returned its verdict: not guilty of sex trafficking and conspiracy to extort, but guilty of two counts of transportation with intent to prostitute. Combs was formally sentenced on October 3. With credit for time served and an additional one-month sentence for alleged violations of prison rules, the disgraced hip hop mogul is eligible for release on June 4, 2028.
2. Justin Baldoni loses defamation case against Blake Lively
Blake Lively closed out 2024 by officially filing a sexual harassment lawsuit against him Finish with us her co-star and director Justin Baldoni on December 31. That same day, Baldoni filed a $250 million defamation lawsuit against The New York Times for her report that Baldoni orchestrated a “smear campaign” against Lively. And so, the stage was set for Lively vs. Baldoni 2025.
On January 16, Baldoni filed a second lawsuit alongside Wayfarer Studios: a $400 million countersuit directed at Lively and her husband Ryan Reynolds, accusing them of hijacking the film and orchestrating a smear campaign against him. In his complaint, Baldoni alleged that Reynolds mocked him by using the character “Nicepool” in Deadpool and Wolverinewhich was released almost at the same time as IEWU. Baldoni’s team then launched an aggressive strategy, posting videos, audio clips, emails, text messages, details of their lawsuits and a timeline of events on a website called “Lawsuit Info.” The website is still available: thelawsuitinfo.com.
The move did not sit well with federal Judge Lewis J. Liman, who warned both sides against litigation in the press and tainting the jury (ABC News).
In March, Reynolds filed a motion to dismiss Baldoni’s defamation lawsuit, arguing that it lacked legal merit and arose solely from Baldoni’s “hurt feelings” about Nicepool. Lively filed her own motion to dismiss two days later, calling Baldoni’s claims an abuse of process and invoking California protections for harassment accusers.
On June 9, Judge Liman dismissed Baldoni’s $400 million countersuit and his $250 million claim against The New York Times. The newspaper subsequently sought compensation from Baldoni and Wayfarer for legal fees.
Taylor Swift became an unexpected figure in the dispute after Baldoni’s team issued subpoenas seeking her communications with Lively, accusing Lively of trying to pressure Swift into publicly pledging her loyalty. Swift’s representatives dismissed the claim as a publicity stunt. The first subpoena was withdrawn, but Baldoni’s team issued another one later that year. They also attempted to depose Swift by handing her deposition documents in front of her fiancé Travis Kelce’s home, but failed (People magazine).
Lively appeared for her deposition on July 31. Shortly afterward, Baldoni’s team submitted an unrevised draft to the court, prompting Lively to take steps to have it removed from court records. In August, Judge Liman granted Lively’s request to unseal evidence that she says shows Baldoni’s team orchestrated a smear campaign. Lively is also seeking millions in attorney fees under the California Protecting Survivors from Armed Defamation Lawsuits Act of 2023, a point Baldoni’s team disputes.
Baldoni’s lawyers argue that the law does not apply to this case since Lively “made up her sexual harassment allegations,” which is what they will try to prove at trial. But will that day really come?
In early December, Judge Liman postponed the trial from March 9 to May 18 because his criminal trials took priority over civil cases. He also advised both sides to consider settling out of court.
3. Kendrick vs. Drake
Drake’s New Year’s resolution for 2025 was to put his feud with Kendrick behind him. On January 3, director Williams released a Drake freestyle track, Fighting the Irishwhere Drizzy reflects on the consequences of the battle and what he described as betrayal within the industry. “I just know this shit is personal to us and it wasn’t just business,” he rapped, framing the dispute as unresolved and deeply felt.
A week later, Drake filed a defamation lawsuit in New York City against his local label, Universal Music Group, accusing the company of promoting Kendrick’s track. not like usa song riddled with “incendiary and shocking accusations.”
UMG backed down and decided to dismiss the lawsuit as an attempt by Drake to “save face” after losing the rap battle to Kendrick.
Meanwhile, Kendrick responded to the lawsuit by mocking Drake onstage at the Super Bowl halftime show. “I want to perform their favorite song, but you know they love to sue,” he joked before performing it anyway. Drake later amended his lawsuit to accuse Lamar of attempting to “assassinate the character of another artist.”
The case reached its turning point in October 2025, when a federal judge dismissed Drake’s lawsuit. The court ruled that Drake had no grounds to sue UMG, noting that Kendrick’s speech was just that: a dissenting speech and a “war of words.”
Drake’s legal team said they intended to appeal the decision. To date, no appeal has been filed.
4. Jay-Z’s double victory
Jay-Z spent much of 2025 going through two legal battles, one involving Diddy and the other shocking paternity claims.
In late 2024, an unnamed woman, represented by attorney Tony Buzbee, accused Jay-Z and Sean “Diddy” Combs of raping her when she was 13 following the 2000 MTV Video Music Awards. As Diddy’s legal troubles mounted, many saw the lawsuit as a potential turning point for Jay-Z as well.
That reckoning never came. In February 2025, the woman abruptly withdrew her lawsuit. A month later, Jay-Z filed a defamation lawsuit against the accuser and Buzbee, alleging that she had “voluntarily admitted” that the claims were false and had been made under duress. His filing described the case as an “evil conspiracy” designed to extort money and damage his reputation. In July, a judge dismissed Jay-Z’s defamation lawsuit, effectively closing that chapter.
The second legal battle was one Jay-Z had been fighting for a decade against a man named Rymir Satterthwaite, who claimed the rapper was his biological father. In November 2025, the case was officially dismissed, ending a decade-long dispute. Jay-Z refused to seek legal fees, thus closing one of the longest legal sagas linked to his name.
5. The Kardashians vs. Ray J
Ray J reignited a decades-long feud with his ex, Kim Kardashian, and her mother, Kris Jenner, in 2025 by responding after they sued him for defamation. In October, Kardashian and Jenner filed a lawsuit alleging that Ray J made “blatantly false” statements accusing them of being on the brink of a federal racketeering investigation and comparing them to Sean “Diddy” Combs’ legal troubles.
In November, Ray J responded with his own legal filing, accusing Kardashian and Jenner of violating a confidential agreement from April 2023. That agreement, he says, included a $6 million payment and a mutual non-disparagement clause that prohibited any future public mention of their infamous 2003 sex tape. Ray J alleges that references to the Kardashian tape violated that agreement, entitling him to damages and undermining the defamation lawsuit against him.
Their counterclaim also revives long-standing claims that Kardashian and Jenner orchestrated the leak of the tape and manipulated public narratives for publicity. The Kardashians’ legal team dismissed their claims as unfounded.
