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 the great filmmaker Harvey Weinstein, who was convicted of rape, and the beloved princess of pop, Britney Spears, who revealed that she was practically forced to perform at gunpoint, the industry’s reckoning has been a long time coming. And while we still have a long way to go, significant progress was made this year.
If you thought 2024 was chaotic, 2025 proved that Hollywood’s legal storm is just beginning.
1. The calculation of Sean ‘Diddy’ Combs
A year after his arrest in September 2024, Sean “Diddy” Combs faced the biggest bill of his career: a federal criminal trial that ran for nearly two months in the summer of 2025. After weighing five factors, the court sentenced Combs to 50 months in prison (4 years) and a $500,000 fine. It could have been much worse; he avoided a potential life sentence after being acquitted of the two major charges – sex trafficking and conspiracy.
The trial, which was not televised, began on May 12 before 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 leaned on a technical distinction central to their case. “Domestic violence is not sex trafficking,” they argued in opening statements, framing the prosecution’s narrative as an assault 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 the age of 19. Her 2023 sexual-assault lawsuit — settled within 24 hours for $20 million — had sparked a wave of more than 70 investigations into Combs and the civil suits brought to Combs’ disposal. On the stand for four days, Cassie described being assaulted by Combs while trying to escape 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 any defense witnesses, nor did Combs take the stand. They opted instead for aggressive cross-examination. Legal analyst Mitchell Epner noted that the strategy signaled confidence: that the prosecution’s witnesses “made our case” and that the defense did not need to present additional testimony to raise a reasonable doubt (USA today).
Several high profile people were drawn into the case. Kid Cudi testified that his car was deliberately blown up during the period he briefly dated Cassie. Other celebrities, such as Usher and Justin Bieber, appeared in online conspiracy theories. Kanye West even showed up at the courthouse one day in support of Combs. Suge Knight, the founder of Death Row Records, publicly defended Combs from prison despite their infamous rivalry. Meanwhile, 50 Cent’s top-streaming Netflix documentary about Combs intensified public scrutiny with footage and allegations stretching back to the 1990s.
After six weeks, the jury returned its verdict: not guilty of sex trafficking and conspiracy, but guilty of two counts of transportation for the purpose of prostitution. Combs was formally sentenced on October 3. With credit for time served and an additional one month in prison for alleged violations of prison rules, the disgraced hip-hop mogul is eligible for release on June 4, 2028.
2. Justin Baldoni loses libel case against Blake Lively
Blake Lively closed out 2024 by officially filing a sexual harassment lawsuit against her It ends with us costar and director Justin Baldoni on December 31. The same day, Baldoni filed a defamation suit for $250 million. New York Times over their report that Baldoni orchestrated a “smear campaign” against Lively. And with that, the stage was set for Lively vs. Baldoni 2025.
On January 16, Baldoni filed another lawsuit along with Wayfarer Studios – a $400 million countersuit against 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”. Deadpool and Wolverinewhich was published around the same time as IEWU. Baldoni’s team then launched an aggressive strategy, releasing videos, audio clips, emails, text messages, details of his trial and a timeline of events on a website called “Trial Information.” The website is still available: thelawsuitinfo.com.
The move did not go down well with federal judge Lewis J. Liman, who warned both sides about conducting trials in the press and tainting a jury (ABC News).
In March, Reynolds filed a motion to dismiss Baldoni’s defamation suit, arguing that it lacked legal basis and stemmed solely from Baldoni’s “hurt feelings” over Nicepool. Lively filed her own motion to dismiss two days later, calling Baldoni’s allegations an abuse of process and invoking California’s protections against harassment accusers.
On June 9, Judge Liman dismissed Baldoni’s $400 million counterclaim and his $250 million lawsuit against New York Times. The newspaper later sought damages from Baldoni and Wayfarer for legal fees.
Taylor Swift became an unexpected figure in the controversy after Baldoni’s team issued subpoenas seeking her communications with Lively, accusing Lively of trying to pressure Swift into publicly pledging her fidelity. Swift’s representatives dismissed the claim as a publicity stunt. The first subpoena was withdrawn, but Baldoni’s team reissued a second one later in the year. They also tried to impeach Swift by serving her deposition papers outside her fiance Travis Kelce’s house, but failed (People magazine).
Lively sat for her deposition on July 31. Soon after, Baldoni’s team filed an unrevised draft with the court, prompting Lively to move to strike it from the court record. In August, Judge Liman granted Lively’s request to disclose evidence she says shows Baldoni’s team orchestrated a smear campaign. Lively is also seeking millions in legal fees under California’s Protecting Survivors from Weaponized Defamation Lawsuit Act of 2023 — a point Baldoni’s team disputes.
Baldoni’s attorneys argue that the law does not apply to this case since Lively “made her allegations of sexual harassment,” which is what they will try to prove at trial. But will that day actually come?
In early December, Judge Liman adjourned the trial from March 9 to May 18 due to his criminal cases taking precedence over civil cases. He also advised both parties to consider settling out of court.
3. Kendrick vs. Drake
Drake’s New Year’s resolution for 2025 was to leave his feud with Kendrick. On January 3rd, conductor Williams released a Drake freestyle track, Fighting Irishwhere Drizzy reflects on the fallout from the battle and what he described as betrayal within the industry. “You just have to know that the matter is personal to us and was not just business,” he rapped, framing the dispute as unresolved and heartfelt.
A week later, Drake filed a defamation suit in New York City against his home label, Universal Music Group, accusing the company of promoting Kendrick’s diss track. Not like usa song filled with “inflammatory and shocking allegations.”
UMG backed down and moved to dismiss the lawsuit as Drake’s attempt to “save face” after losing the rap battle to Kendrick.
Meanwhile, Kendrick responded to the lawsuit by mocking Drake at the Super Bowl halftime show. “I want to perform their favorite song, but you know they love to sue,” he teased before performing it anyway. Drake subsequently amended his lawsuit to accuse Lamar of attempting to “assassinate another artist’s character.”
The case reached its turning point in October 2025, when a federal judge dismissed Drake’s lawsuit. The court ruled that Drake had no cause to sue UMG, noting that Kendrick’s diss was just that — a diss track and a “war of words.”
Drake’s legal team said they intended to appeal the ruling. So far, there has been no appeal.
4. Jay-Z’s double win
Jay-Z spent much of 2025 navigating two legal battles, one involving Diddy and the other shocking paternity claims.
In late 2024, an anonymous woman, represented by attorney Tony Buzbee, accused Jay-Z and Sean “Diddy” Combs of raping her when she was 13 years old after the 2000 MTV Video Music Awards. As Diddy’s legal problems mounted, many saw the trial as a potential turning point for Jay-Z as well.
That bill never came. In February 2025, the woman abruptly withdrew her lawsuit. A month later, Jay-Z filed a defamation suit against both the accuser and Buzbee, alleging that she had “voluntarily admitted” that the allegations were false and 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 suit, effectively closing that chapter.
The other 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 the decade-long dispute. Jay-Z declined to seek legal fees, closing one of the longest-running legal sagas associated with his name.
5. The Kardashians vs. Ray J
Ray J reignited a decades-old feud with his ex, Kim Kardashian, and her mother, Kris Jenner, in 2025 by firing back after they sued him for defamation. In October, Kardashian and Jenner filed a lawsuit claiming Ray J made “patently false” statements that accused them of being on the brink of a federal racketeering investigation and compared them to Sean “Diddy” Combs’ legal troubles.
In November, Ray J responded with his own legal filing, accusing Kardashian and Jenner of breaching a confidential settlement agreement from April 2023. That agreement, he says, included a $6 million payment and a mutual non-disparagement clause preventing any future public mention of their infamous 2003 sex tape. Ray J claims that references to the tape about The Kardashians violated that agreement, entitling him to damages and undermining the defamation claim against him.
His cross-complaint also revives long-standing allegations that Kardashian and Jenner orchestrated the leak of the tape and manipulated public narratives to the public. The Kardashians’ legal team has dismissed his claims as unfounded.
