The scandal surrounding Sean "Diddy" Combs' sex trafficking "criminal enterprise" has Hollywood on its toes ahead of his trial, set to begin on May 5, 2025.
The revelation turned a once beloved and admired celebrity into a monster, with many now viewing him as the latest symbol of the darker, more sinister side of fame and power.
Diddy's fall from grace echoes the tales of past celebrities whose dark secrets destroyed their lives—and those of others—from Harvey Weinstein's decades-long abuse of actresses to Jeffrey Epstein's underage sex trafficking ring to Michael Jackson's child abuse charges.
Here are some of the darkest scandals in Hollywood history that rival—or even surpass—Diddy's crimes.
#1 Harvey Weinstein
Almost no Hollywood scandal compares to the fall of Harvey Weinstein. Feared as an all-powerful movie mogul, Weinstein abused his position by taking advantage of actresses for decades, exchanging sexual favors for career opportunities.
Weinstein's predatory empire came crashing down when multiple actresses, including Ashley Judd and Rose McGowan, came forward with damning allegations in October 2017. More high-profile names, like Angelina Jolie and Gwyneth Paltrow, also gave details on the producer's unwanted advances toward them.
What followed was a bitter legal battle between Weinstein and his production company, which ended with his arrest in 2018 and subsequent conviction for rape and sexual assault in 2020.
Harvey Weinstein was condemned to 16 years in prison and is currently serving time at Rikers Island Prison, New York.
Weinstein's predatory empire came crashing down when multiple actresses, including Ashley Judd and Rose McGowan, came forward with damning allegations in October 2017. More high-profile names, like Angelina Jolie and Gwyneth Paltrow, also gave details on the producer's unwanted advances toward them.
What followed was a bitter legal battle between Weinstein and his production company, which ended with his arrest in 2018 and subsequent conviction for rape and sexual assault in 2020.
Harvey Weinstein was condemned to 16 years in prison and is currently serving time at Rikers Island Prison, New York.
22points
#2 R. Kelly
Robert Sylvester Kelly, known mainly by his stage name, R. Kelly, was once hailed as an all-time great of the R&B genre before his reputation crashed.
The artist faced repeated accusations of sexual abuse towards minors and was the subject of a long-term investigation that began in August 2000. The shocking documentary Surviving R. Kelly exposed the full extent of his predatory behavior, which his inner circle had enabled for decades.
In 1996, a woman named Tiffany Hawkins alleged that Kelly had been intimate with her when she was 15 and he was 24, and had asked her to invite other friends of similar age to participate in intimate videos.
Despite the allegations, it wasn't until 2021 that Kelly was convicted of sex trafficking and racketeering. He remains incarcerated to this day.
The artist faced repeated accusations of sexual abuse towards minors and was the subject of a long-term investigation that began in August 2000. The shocking documentary Surviving R. Kelly exposed the full extent of his predatory behavior, which his inner circle had enabled for decades.
In 1996, a woman named Tiffany Hawkins alleged that Kelly had been intimate with her when she was 15 and he was 24, and had asked her to invite other friends of similar age to participate in intimate videos.
Despite the allegations, it wasn't until 2021 that Kelly was convicted of sex trafficking and racketeering. He remains incarcerated to this day.
20points
#3 Jeffrey Epstein
Epstein's scandal shocked the world, not only because of the depth of his criminal enterprise and the depravity of his crimes, but also because it established links between influential people and his illicit activities.
Called the "little black book," the financier had the names of many Hollywood elites who presumably participated in the sex trafficking of minors, with girls identified in court documents to be as young as 14 years old.
His private island and jet were reportedly frequented by notorious pop culture figures, causing further outrage as more victims shared their stories of abuse.
Epstein was first convicted in 2008 and then again in July 2019. He died of a self-harming incident while incarcerated, but many believe he was instead assassinated due to the danger his knowledge posed to celebrities and other famous people.
Called the "little black book," the financier had the names of many Hollywood elites who presumably participated in the sex trafficking of minors, with girls identified in court documents to be as young as 14 years old.
His private island and jet were reportedly frequented by notorious pop culture figures, causing further outrage as more victims shared their stories of abuse.
Epstein was first convicted in 2008 and then again in July 2019. He died of a self-harming incident while incarcerated, but many believe he was instead assassinated due to the danger his knowledge posed to celebrities and other famous people.
18points
#4 Bill Cosby
Once known as America's Dad, Bill Cosby's public image was shattered after more than 60 women accused him of drugging and sexually assaulting them over several decades.
Cosby's wholesome, comedic persona masked the predatory behavior he allegedly exhibited behind closed doors, including a variety of crimes such as rape, drug-facilitated sexual assault, sexual battery, child sexual abuse, and sexual harassment.
From 1965 to 2008, Cosby operated with impunity, using the power he garnered from his participation in The Cosby Show to strong-arm those who would speak out against him.
The actor was sentenced to 10 years in prison in 2018. The Pennsylvania highest court overturned his conviction in July 2021, and the US Supreme Court declined to review his case in March 2022, leaving him a free man.
Cosby's wholesome, comedic persona masked the predatory behavior he allegedly exhibited behind closed doors, including a variety of crimes such as rape, drug-facilitated sexual assault, sexual battery, child sexual abuse, and sexual harassment.
From 1965 to 2008, Cosby operated with impunity, using the power he garnered from his participation in The Cosby Show to strong-arm those who would speak out against him.
The actor was sentenced to 10 years in prison in 2018. The Pennsylvania highest court overturned his conviction in July 2021, and the US Supreme Court declined to review his case in March 2022, leaving him a free man.
18points
#5 Phil Spector
Hailed as a legendary music producer, Spector's legacy took a dark turn on February 3, 2003, when actress Lana Clarkson was found dead from a gunshot wound in his mansion.
Spector was arrested that same day but was released on $1 million bail. The investigation continued until March 19, 2007, when he faced his first murder trial. The prosecution pointed to his history of threatening women with firearms while intoxicated, stating that Clarkson's death was a result of such behavior.
The producer was convicted on April 13, 2009, after a second trial presented forensic evidence that detailed the trajectory of the killing bullet, dismantling Spector's defense claims that the death was a result of self-harm.
Spector was sentenced to 19 years in prison on May 29, 2009, and died in prison at the age of 81 from complications related to COVID-19 on January 16, 2021.
Spector was arrested that same day but was released on $1 million bail. The investigation continued until March 19, 2007, when he faced his first murder trial. The prosecution pointed to his history of threatening women with firearms while intoxicated, stating that Clarkson's death was a result of such behavior.
The producer was convicted on April 13, 2009, after a second trial presented forensic evidence that detailed the trajectory of the killing bullet, dismantling Spector's defense claims that the death was a result of self-harm.
Spector was sentenced to 19 years in prison on May 29, 2009, and died in prison at the age of 81 from complications related to COVID-19 on January 16, 2021.
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18points
#6 O. J. Simpson
O.J. Simpson, a man once regarded as a star on the football field and in movies alike, has become a household name for all the wrong reasons.
June 12, 1994—the day on which his ex-wife Nicole Brown Simpson and her friend Ronald Goldman were gruesomely murdered just outside her house in Brentwood,—was one of the most tumultuous days of O.J. Simpson's life. Even though O.J. Simpson protested his innocence, evidence continued to build against him.
Simpson was charged with the murders, and on June 17, 1994, he became the fugitive of a nationally broadcast "low-speed chase"—infamously, Simpson drove on a highway in a white Ford Bronco while being pursued by police cars.
Simpson was found not guilty by the jury on October 3, 1995, in what has been characterized as one of the most contentious decisions in US legal history. A civil jury later that year came to a very different conclusion, pronouncing O.J. Simpson responsible for the wrongful deaths of Nicole Brown and Rosen Goldman and ordering him compensate $33.5 million.
Simpson's legal issues returned in 2007, when he was arrested for armed robbery and kidnapping in Las Vegas. In 2008, he was tried and convicted for the offense and handed a prison sentence of 33 years. After completing nine years of his sentence, he was placed on parole in 2017 and set free.
June 12, 1994—the day on which his ex-wife Nicole Brown Simpson and her friend Ronald Goldman were gruesomely murdered just outside her house in Brentwood,—was one of the most tumultuous days of O.J. Simpson's life. Even though O.J. Simpson protested his innocence, evidence continued to build against him.
Simpson was charged with the murders, and on June 17, 1994, he became the fugitive of a nationally broadcast "low-speed chase"—infamously, Simpson drove on a highway in a white Ford Bronco while being pursued by police cars.
Simpson was found not guilty by the jury on October 3, 1995, in what has been characterized as one of the most contentious decisions in US legal history. A civil jury later that year came to a very different conclusion, pronouncing O.J. Simpson responsible for the wrongful deaths of Nicole Brown and Rosen Goldman and ordering him compensate $33.5 million.
Simpson's legal issues returned in 2007, when he was arrested for armed robbery and kidnapping in Las Vegas. In 2008, he was tried and convicted for the offense and handed a prison sentence of 33 years. After completing nine years of his sentence, he was placed on parole in 2017 and set free.
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15points
#7 Roman Polanski
Roman Polanski's 1977 rape case continues to haunt Hollywood to this day. The acclaimed director was arrested and charged with six offenses against a 12-year-old girl in Los Angeles.
Polanski's crimes included intercourse with a minor, using drugs to facilitate the act, perversion, and sodomy.
While the director, famous for films like The Pianist and Rosemary's Baby, initially pleaded not guilty to all charges, he later accepted a plea bargain in exchange for a reduction in his eventual sentence. Polanski also underwent a psychiatric evaluation, but its results were not conclusive enough to prevent him from going to jail.
Polanski fled to England and France in February 1978 and has since avoided justice. Efforts to extradite him to the United States to face criminal charges have been unsuccessful, but a trial next year opens a new path for the 90-year-old to be held accountable.
Polanski is set to face American justice on August 4, 2025.
Polanski's crimes included intercourse with a minor, using drugs to facilitate the act, perversion, and sodomy.
While the director, famous for films like The Pianist and Rosemary's Baby, initially pleaded not guilty to all charges, he later accepted a plea bargain in exchange for a reduction in his eventual sentence. Polanski also underwent a psychiatric evaluation, but its results were not conclusive enough to prevent him from going to jail.
Polanski fled to England and France in February 1978 and has since avoided justice. Efforts to extradite him to the United States to face criminal charges have been unsuccessful, but a trial next year opens a new path for the 90-year-old to be held accountable.
Polanski is set to face American justice on August 4, 2025.
14points
#8 Woody Allen
Woody Allen's relationship with his adopted daughter, Soon-Yi Previn, has long been controversial. Still, it was the allegations from his other adopted daughter, Dylan Farrow, that cast a permanent shadow on his legacy.
Dylan accused Allen of molesting her when she was just seven years old, an accusation that resurfaced in the media years later.
Though Allen has denied the claims and no charges were brought, the scandal has led to widespread debate about his personal life and relationships.
The accusations were brought to light by Allen's former partner, Mia Farrow, igniting a bitter custody battle that dragged the ugly details of their family life into the public eye.
Allen's continued success in Hollywood has been controversial, with some defending him and others distancing themselves from his work. While the truth remains disputed, the mere presence of such serious allegations has permanently tarnished his career.
Dylan accused Allen of molesting her when she was just seven years old, an accusation that resurfaced in the media years later.
Though Allen has denied the claims and no charges were brought, the scandal has led to widespread debate about his personal life and relationships.
The accusations were brought to light by Allen's former partner, Mia Farrow, igniting a bitter custody battle that dragged the ugly details of their family life into the public eye.
Allen's continued success in Hollywood has been controversial, with some defending him and others distancing themselves from his work. While the truth remains disputed, the mere presence of such serious allegations has permanently tarnished his career.
14points
#9 Michael Jackson
While few people doubt Jackson's status as the King of Pop, or the impact of his pop-culture-defining career, the disturbing allegations of child abuse that dogged his personal life have forever tarnished his image.
According to details revealed by one of the alleged victims in the 2019 documentary Leaving Neverland, the artist began his illicit activities in December 1986, when he met 10-year-old James Safechuk while filming a Pepsi commercial.
According to James, Jackson was interested in him and befriended his family, lavishing them with gifts. The boy's parents eventually allowed Jackson to travel alone with their son, which led to them sleeping together.
In August 1993, the Los Angeles police launched an investigation against Jackson based on allegations he had molested four children. The accusations were later supported by Michael's sister, La Toya, who said that she was unwilling to be "a silent collaborator of his crimes against small, innocent children."
The controversy surrounding Jackson followed him until his death in June 2009. His fans defend him to this day, stating that he did nothing wrong and that the families of the children were attempting to extort him for money, while detractors believe the testimony of his alleged victims.
According to details revealed by one of the alleged victims in the 2019 documentary Leaving Neverland, the artist began his illicit activities in December 1986, when he met 10-year-old James Safechuk while filming a Pepsi commercial.
According to James, Jackson was interested in him and befriended his family, lavishing them with gifts. The boy's parents eventually allowed Jackson to travel alone with their son, which led to them sleeping together.
In August 1993, the Los Angeles police launched an investigation against Jackson based on allegations he had molested four children. The accusations were later supported by Michael's sister, La Toya, who said that she was unwilling to be "a silent collaborator of his crimes against small, innocent children."
The controversy surrounding Jackson followed him until his death in June 2009. His fans defend him to this day, stating that he did nothing wrong and that the families of the children were attempting to extort him for money, while detractors believe the testimony of his alleged victims.
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14points
#10 Robert Blake
The American actor, best known for his roles in Baretta and Cold Blood, went from famous to infamous after being involved in a murder scandal surrounding the death of his wife, Bonny Lee Bakley, in 2001.
In late 1999, Bonny had earned a reputation for targeting celebrities for financial gain. She became involved with Christian Brando (Marlon Brando's son) and claimed he was the father of a daughter she gave birth in June 2000.
A DNA test confirmed that Brando was not the father, and that Robert Blake was, which led to their marriage on November 19, 2000. Described as forced, the union experienced issues early on, with Bonny moving into a guesthouse on Blake's property rather than living with him.
Bonny was found shot to death outside a restaurant on May 4, 2001, and Blake became the prime suspect.
Blake claimed he had left his wife in the car to retrieve a gun he had forgotten at the restaurant, but investigators didn't believe him.
In April 2002, Blake was arrested and charged with murder. In 2005, he was acquitted of the charges but ordered to pay $15 million to Bonny's family, which caused him to declare bankruptcy shortly thereafter.
In late 1999, Bonny had earned a reputation for targeting celebrities for financial gain. She became involved with Christian Brando (Marlon Brando's son) and claimed he was the father of a daughter she gave birth in June 2000.
A DNA test confirmed that Brando was not the father, and that Robert Blake was, which led to their marriage on November 19, 2000. Described as forced, the union experienced issues early on, with Bonny moving into a guesthouse on Blake's property rather than living with him.
Bonny was found shot to death outside a restaurant on May 4, 2001, and Blake became the prime suspect.
Blake claimed he had left his wife in the car to retrieve a gun he had forgotten at the restaurant, but investigators didn't believe him.
In April 2002, Blake was arrested and charged with murder. In 2005, he was acquitted of the charges but ordered to pay $15 million to Bonny's family, which caused him to declare bankruptcy shortly thereafter.
11points