Famous Personalities Imprisoned: Ranging from R. Kelly and Sean Combs (Diddy) to Harvey Weinstein, television star Danny Masterson from That '70s Show, and Elizabeth Holmes of Theranos.
Life in the limelight often comes with a heaping dose of luxury and adoration that many can only envision. However, the fairy tale can occasionally crumble, leaving those once glorified in the public eye to find themselves behind bars rather than on the red carpet.
From financial misdeeds like corruption and tax evasion to more nefarious acts such as sexual assault and even murder, numerous celebrities who once basked in the limelight have since traded their designer duds for prison jumpsuits, serving lengthy sentences for their criminal behaviors. Let's take a glimpse at a few celebrities currently performing their sentences, largely funded by the taxpayers.
R. Kelly, 58
R. Kelly was slapped with a 30-year prison sentence in June 2022 after being convicted on charges of producing child pornography and procuring young girls for sex. Originally held at a facility in Chicago, Illinois, he was transported to a federal prison in North Carolina in 2023. He continues to wage legal battles regarding additional charges and appeals linked to his convictions.
Sean "Diddy" Combs, 55
Diddy, the music mogul, was arrested in September 2024 and faces charges of sex trafficking and racketeering, related to decades-old allegations of sexual assault and violence. Over two dozen accusers claim he exploited his industry power to facilitate these acts. His trial is slated to begin May 5, 2025, and he is currently locked up at Brooklyn's Metropolitan Detention Center, sharing a cell with Sam Bankman-Fried.
Danny Masterson, 49
Masterson, best known for his role in That '70s Show, was sentenced to 30 years to life for raping two women in the early 2000s. At 49, he remains incarcerated as of April 2025.
Other Notables
Karen Huger, from The Real Housewives of Potomac, started a two-year sentence (with one year suspended) in February 2025 due to a 2024 DUI arrest. According to fellow cast members, she is considered safe and well-regarded by other inmates. The disgraced ex-congressman George Santos received an 87-month sentence (7 years, 3 months) for wire fraud, identity theft, and embezzling campaign funds, set to begin serving in July 2025. He'll need to cough up over half a million dollars in restitution.
- In 2022, R. Kelly, a well-known figure in the entertainment industry, received a 30-year prison sentence for child pornography and sex-related charges, transitioning from designer duds to a prison jumpsuit.
- Despite his status as a music mogul, Sean "Diddy" Combs was arrested in 2024 and is currently facing sex trafficking and racketeering charges, with trials scheduled to begin in May 2025.
- Danny Masterson, famous for his role in That '70s Show, was sentenced to 30 years to life in prison for rape charges in the early 2000s and remains incarcerated as of April 2025.
- Notable personalities like Karen Huger from The Real Housewives of Potomac and the disgraced ex-congressman George Santos have also been incarcerated, with Huger serving a two-year sentence (with one year suspended) for a 2024 DUI and Santos receiving an 87-month sentence for fraud, identity theft, and embezzlement starting in July 2025.
- From business leaders to entertainment celebrities, plenty of public figures have found themselves behind bars due to crimes, with general news and crime-and-justice sectors keeping the public informed about their ongoing trials and sentences in 2022 and beyond.
