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6 Celebrities Behind Bars: R. Kelly, Diddy, Harvey Weinstein, Danny Masterson from That ’70s Show, and Elizabeth Holmes of Theranos

Celebrities Behind Bars: A Look at Fame’s Dark Side

Fame and fortune often come with glamorous perks, but the glitter can quickly fade, leading some celebrities to prison. High-profile figures have faced serious legal repercussions for crimes ranging from financial corruption to sexual assault and even murder. Here are notable stars currently serving time for their offenses.

R. Kelly, 58
The R&B singer R. Kelly, known for his chart-topping hits, is serving a 30-year prison sentence after being convicted in June 2022 for producing child pornography and enticing minors for sex. His case sparked widespread discussions about accountability in the entertainment industry. After initially being held in Chicago, Kelly was transferred to a federal prison in North Carolina in 2023, where he continues to battle additional charges and appeals.

Diddy, 55
Sean "Diddy" Combs, the acclaimed music producer and entrepreneur, found himself in legal turmoil after his arrest in September 2024 on charges of sex trafficking and racketeering. This arrest comes amid numerous civil lawsuits alleging sexual assault and violence dating back to the 1990s. While Combs denies all allegations, his trial is set for May 2025, as he awaits proceedings from the Metropolitan Detention Center in Brooklyn.

Danny Masterson, 49
Former "That ’70s Show" actor Danny Masterson was sentenced in September 2023 to 30 years to life in prison for the rape of two women. Prosecutors argued that his fame allowed him to evade consequences for his actions in the early 2000s. Masterson, currently incarcerated in San Luis Obispo County, is appealing his conviction, claiming he did not receive a fair trial.

These cases highlight a grim reality that even those at the pinnacle of success can fall from grace, facing serious accountability for their actions.

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