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Lynn Farah

A life of fame and fortune comes with plenty of perks most people can only dream of. But every so often, the fairy tale unravels and those that had been put on a pedestal end up in prison instead.
From financial corruption and tax evasion to more sinister crimes like sexual assault and even murder, plenty of celebrities who once lived a life of luxury have since swapped their designer outfits for prison jumpsuits while serving hefty jail sentences for their crimes. Here are some of the most famous faces currently doing time on the taxpayer’s dime.
R. Kelly, 58

R&B singer R. Kelly has faced multiple allegations of sexual misconduct and abuse, particularly involving minors, in a case that made global headlines and prompted widespread discussions about accountability in the entertainment industry.
In June 2022, he was convicted on charges of producing child pornography and enticing young girls for sex, leading to a hefty 30-year prison sentence, per AP. He was initially being held at a facility in Chicago, Illinois, but was transferred to a federal prison in North Carolina in 2023 according to CNN. Since then, he’s continued to fight legal battles over additional charges and appeals related to his convictions.
Diddy, 55

Sean “Diddy” Combs was once on the brink of billionaire status thanks to his high-flying music career and business ventures, per Forbes. However, following his September 2024 arrest in New York, he now faces trial for sex trafficking and racketeering. This arrest comes amid numerous civil lawsuits alleging sexual assault and violence dating back to the 1990s. Over two dozen people have accused Combs of leveraging his industry influence for drugging, assaulting, and raping them, and having his employees assist in his exploits. Combs denies all allegations, with his trial date set for May 5. He is currently being held in the Metropolitan Detention Center in Brooklyn, New York, where he shares a unit with disgraced crypto mogul Sam Bankman-Fried, who is serving a 25-year sentence for conspiracy, fraud and money laundering, notes The New York Times.
Danny Masterson, 49

In September 2023, American actor Danny Masterson was given a sentence of 30 years to life in prison for raping two women. At the time of his crimes in the early 2000s, Masterson was a popular cast member of the television series That ‘70s Show. Prosecutors claimed that Masterson, a prominent Scientologist, leveraged his high-profile status to avoid responsibility for his actions, per the BBC. Masterson, currently housed at a prison in San Luis Obispo County, is challenging his conviction, with his lawyers arguing that he didn’t receive a fair trial, per CBS News.
Harvey Weinstein, 73

The entertainment industry erupted in 2017 when The New York Times published a story exposing decades of allegations of sexual harassment against Harvey Weinstein, including accusations from actresses Rose McGowan and Ashley Judd. The film mogul was eventually convicted in 2020 on multiple counts of sexual assault and rape. He faced trial for crimes committed against more than 100 women over two decades, with the case ultimately leading to the #MeToo movement. Weinstein was sentenced to 23 years in prison and was being held at New York’s Mohawk Correctional Facility. In 2021 he was extradited to California, and in 2023, a Los Angeles judge jailed him for another 16 years for rape and sexual assault, per Sky News.
Elizabeth Holmes, 41

Once hailed by Forbes as the world’s youngest self-made woman billionaire, biotechnology entrepreneur Elizabeth Holmes was a regular in the spotlight, often appearing with celebrities at major events. But her world came crashing down in January 2022 when she was convicted of defrauding investors with her blood-testing company, Theranos, following a Wall Street Journal exposé that revealed her blood testing devices didn’t work. She is presently serving an 11-year and three-month sentence at Federal Prison Camp Bryan in Texas. However, this sentence has been shortened twice already: first by two years, and then by over four months in May 2024, per CNN. The fascination with Holmes lead Hulu to create TV series The Dropout, with Amanda Seyfried playing the part of the disgraced entrepreneur.
Jen Shah, 51

Incarcerated alongside Elizabeth Holmes at Federal Prison Camp Bryan is reality star Jen Shah – a former cast member on The Real Housewives of Salt Lake City – who is serving a six and a half year prison sentence for her role in a telemarketing fraud scheme. Shah’s case shocked the entertainment world when she was found guilty of running a nationwide telemarketing fraud scheme that targeted elderly people. Like Holmes, Shah’s sentence has since been reduced twice – first by one year, and later by a further eight months, per NBC.
Holmes and Shah have reportedly struck up an unlikely friendship during their time behind bars, and have been photographed spending time together on the prison grounds. According the Daily Mail, the Bravo star hosts workout classes for fellow inmates, with Holmes regularly attending the sessions.


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Fame and celebrity

6 celebrities currently in jail – from R. Kelly and Diddy to Harvey Weinstein, That ‘70s Show’s Danny Masterson and Theranos’ Elizabeth Holmes

Danny Masterson, Elizabeth Holmes and R. Kelly are all serving time in prison. Photos: AP, AFP, TNS

Musician R. Kelly emerges from his Chicago studio to turn himself in to Chicago police in February 2019. Photo: TNS

Producer-musician Sean “Diddy” Combs’ trial is set to begin in early May. Photo: Getty Images via AFP/TNS

Actor Danny Masterson was sentenced to 30 years to life in prison for raping two women. Photo: Getty Images via AFP

Harvey Weinstein appears in criminal court in September 2024, in New York City. Photo: Getty Images via TNS

Former Theranos CEO Elizabeth Holmes leaves federal court in San Jose, California, in March 2023. Photo: AP Photo

The Real Housewives of Salt Lake City’s Jen Shah is currently doing time in Texas. Photo: @therealjenshah/Instagram

Who is disgraced Backstreet Boy Nick Carter’s wife, Lauren Kitt Carter? The ‘Everybody’ singer met the former fitness YouTuber through his siblings, and they share 3 children together

Meet disgraced Backstreet Boy Nick Carter’s wife, Lauren Kitt Carter. Photo: @laurenkittcarter/Instagram 

Nick Carter has been accused of sexual assault by four women. Photo: NBCU Photo Bank via Getty Images

Nick Carter, Lauren Kitt Carter and their children celebrating Christmas in 2020. Photo: @laurenkittcarter/Instagram 

Lauren Kitt Carter has been married to Backstreet Boy Nick Carter since 2014. Photo: @laurenkittcarter/Instagram

Nick Carter and Lauren Kitt Carter met at a movie night at his house. Photo: @laurenkittcarter/Instagram 

Nick Carter proposed to Lauren Kitt Carter in 2013 in the Florida Keys. Photo: @laurenkittcarter/Instagram

Lauren Kitt Carter and Nick Carter have three children: Odin, Saoirse and Pearl. Photo: @laurenkittcarter/Instagram 

Bollywood’s 5 richest actresses – net worths, ranked: Priyanka Chopra, Aishwarya Rai Bachchan and Alia Bhatt have made millions from films, investments and business ventures – but who’s the richest?

(From left) Priyanka Chopra, Alia Bhatt and Deepika Padukone are among the world’s five richest Bollywood actresses. Photos: @priyankachopra, @aliaabhatt/Instagram; Cartier

Actress, producer and former model Deepika Padukone is No 5 on our list. Photo: @deepikapadukone/Instagram

The youngest woman on the Bollywood actress rich list is Alia Bhatt. Photo: @aliaabhatt/Instagram

Priyanka Chopra is a sought-after brand ambassador, endorsing luxury brands such as Dior, Bulgari and Ralph Lauren. Photo: @priyankachopra/Instagram

Former Miss World Aishwarya Rai Bachchan comes in at No 2 on our list. Photo: @aishwaryaraibachchan_arb/Instagram

Juhi Chawla is way out in front on the Bollywood actress rich list mainly thanks to her successful business ventures. Photo: @iamjuhichawla/Instagram

Inside Hollywood veteran James Toback’s fall from grace: a New York jury awarded US$1.68 billion to 40 women who accused him of sexual abuse over a span of 35 years, marking a huge #MeToo victory

A New York jury has awarded US$1.68 billion to 40 women who accused Hollywood veteran James Toback of sexual abuse over a span of 35 years. Photo: TNS

James Toback developed a gambling addiction while working as a university lecturer. Photo: AP

James Toback at HBO’s Summer 2013 TCA Panel at the Beverly Hilton Hotel, in California. Photo: AP

James Toback onstage at the 2016 AJHS Emma Lazarus Statue of Liberty Award Dinner in New York, in December 2016. Photo: Getty Images

Robert Downey Jr starred in James Toback’s 1987 film The Pick-up Artist. Photo: AFP

James Toback, Stephanie Toback and their son Andre Toback walk the red carpet ahead of a screening of The Leisure Seeker during the 2017 Venice Film Festival. Photo: Getty Images

Who is Russell Simmons’ accuser Drew Dixon – and why did she subpoena Oprah Winfrey? The ex-Def Jam exec, who worked with Pharrell and Lauryn Hill, also went to university with Diddy

Drew Dixon has involved Oprah Winfrey in her lawsuit against former record executive Russell Simmons. Photos: Instagram

Oprah Winfrey has been subpoenaed by former record company executive Drew Dixon. Photo: @oprah/Instagram

Russell Simmons has been accused by numerous women of sexual assault. Photo: TNS

Drew Dixon gives a #MeToo keynote address in 2022. Photo: @deardrewdixon/Instagram 

Drew Dixon went to Howard University at the same time as Sean “Diddy” Combs. Photo: @deardrewdixon/Instagram 

Drew Dixon (right) and professor Anita Hill. Photo: @deardrewdixon/Instagram 

Drew Dixon featured in HBO Max documentary On the Record. Photo: @deardrewdixon/Instagram 

Drew Dixon at her 30-year Stanford reunion in 2022. Photo: @deardrewdixon/Instagram 

Drew Dixon with her two children. Photo: @deardrewdixon/Instagram 

Drew Dixon with her daughter. Photo: @deardrewdixon/Instagram 

Sean ‘Diddy’ Combs and Ashton Kutcher’s close friendship: the actor said they became ‘fast friends’ and that ‘if you’re a single man, there’s no greater human being in the world than him’

Ashton Kutcher and Sean “Diddy” Combs were friends for years – so how much does the actor know about the criminal charges being brought against the rapper? Photos: Getty Images, WireImage

Disgraced music mogul Sean “Diddy” Combs is set to appear in court in May. Photo: Invision/AP

Sean “Diddy” Combs and Ashton Kutcher were close friends who regularly partied together. Photo: FilmMagic

Ashton Kutcher, a 12-year-old Daveigh Chase and Sean “Diddy” Combs in 2003. Photo: WireImage for VH-1

Actor Ashton Kutcher reportedly stopped clubbing with Sean “Diddy” Combs after he began dating actress Demi Moore. Photo: Getty Images

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From R&B legends and a Real Housewife to a former sitcom star – these famous folks sensationally went from riches to rags overnight … and are still paying for their crimes


From R&B legends and a Real Housewife to a former sitcom star – these famous folks sensationally went from riches to rags overnight … and are still paying for their crimes.


6 celebrities currently in jail – from R. Kelly and Diddy to Harvey Weinstein, That ‘70s Show’s Danny Masterson and Theranos’ Elizabeth Holmes

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R. Kelly, 58