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How do celebrity prisoners survive in jail?

Robert Downey Jr. at the premiere of Disney and Marvel's 'Avengers: Infinity War
Robert Downey Jr. went to prison for violating his probation back in 1999 | Image: Tinseltown /

Prisons are not fun places to be. Despite the clichéd cries from folk who have generally never spent any time inside, they’re not holiday camps. Whether or not inmates have access to televisions or not. Deprive a human of their freedom and liberty and lock them in a tiny room for most of the day and you’ll see it’s not exactly a fun little jolly for them.

Is this the case for all convicts, though? Or is there a hierarchy? A pecking order? Do VIP prisoners exist? If so, it seems likely that famous people who find themselves serving time might likely fall into this category. Or, it may well be the case that prison life is even tougher for them. With guards and inmates targeting them and making their lives even more Hellish.

Let’s investigate how celebrity prisoners survive in jail by taking a look at the stretches of some rather famous faces that have spent time in the clink…

Robert Downey Jr.

Future Iron Man Robert Downey Jr. went to prison for violating his probation back in 1999. He was handed down a three-year prison term at the California Substance Abuse Treatment Facility and State Prison in California, serving only one full year of his sentence. He was on probation for a series of drugs and handgun charges. This followed on from having already spent six months in the LA County jail.

Despite having used the same lawyer as OJ Simpson, Robert Shapiro, the actor couldn't swerve real lock-up time. He shared a four-man cell and - it's believed - that Downey Jr. may have been the victim of bullying, beatings and even sexual assault during his time in jail. Although this has never been confirmed by the actor or his team. By all accounts, fellow inmates took exception to the Chaplin star slinking off to give interviews with huge newspapers and meeting up with Hollywood pals like Sean Penn.

Martha Stewart

America’s domestic goddess Martha Stewart, is not someone you can imagine going to prison. But sent down she was. In July 2004, Stewart was sentenced to serve a full five-month term in a federal correctional facility for insider trading, securities fraud and obstruction of justice.

The popular TV personality served her time at Alderson, a fenceless jail known as 'Camp Cupcake.' After her stretch, Stewart had a period of house arrest - in her mansion - which she described as 'hideous'. The funny thing was that she was said to have enjoyed her time giving yoga classes at Camp Cupcake, such were her privileges and the comfort and esteem she enjoyed there.

OJ Simpson

Captain Richard Adams is the supervisor of the 7,200-bed Men’s Central Jail in LA. In there is a former clinic called 'Room 7021', 80 square feet of comparatively luxurious cell space. A haven away from the overcrowded jungle of the rest of the prison. OJ Simpson spent a full year of his sentence there. Why? Was it favouritism or for his protection? Adams claims it's the latter.

'This is not a hotel and we don’t give celebrities special treatment. The guys in here will prey on them and eat them alive, so off to protective custody they go. I don’t want anyone getting hurt in here.'

Bill Cosby

The world was shocked when the stories emerged about Bill Cosby's sexual assault allegations. It was shocked again when he found himself jailed in The Big House with other serious offenders in 2018. His conviction was overturned three years later.

In his time in prison, rumours floated around of Cosby getting into trouble with other inmates. His legal team and family were quick to deny that Cosby has gotten into several fights in the lunch hall. Apparently, chicken burgers and fruit had been thrown at him by other cons. No word on whether any pudding was chucked in Cosby’s direction.

Lindsay Lohan/Nicole Ritchie/Michelle Rodriguez

Quick glances over the prison experiences of three US celebrities arrested in 2006 and 2007 paint a worrying picture of special treatment. Tabloid favourites Lindsay Lohan and Nicole Ritchie were both arrested and sent down for various drugs and driving charges some 15 years ago.

Neither was in the can for more than 90 minutes. Fast and Furious actress Rodriguez served just four and a half hours of her sentence for a DUI hit and run.

Authorities claim that prison overcrowding saw these ‘non-violent offenders’ released early and none of the women were the beneficiaries of preferential treatment.

Both Hilton and Rodriguez later found themselves arrested and shown a cell once more. Again, neither served much time, strolling back out within a matter of weeks.

It seems likely that prosecutors would not have been happy with these headlines. Especially given the average person would likely have served much more time. After all, the US legal system is rarely thought of as lax, is it?

One aspect leaves a particularly sour taste in the mouth. It was later revealed that Paris Hilton’s grandfather, the billionaire William Barron Hilton, donated a sizeable cheque to LA County Sheriff Baca’s election campaign. Did this account for Paris' seemingly lenient sentence? Or for the fact that her parents, when visiting, got to cut the queue and have the visiting area roped off?

'This is L.A.,' Sheriff’s Department spokesman Steve Whitmore offered by way of explanation. 'The mayor, the City Council and other elected officials all have people in show business who donate to their campaigns.'

Dr. Dre

Rapper and producer Dr. Dre (real name Andre Young) was jailed in 1994 for a probation violation, having previously been arrested for battery and a DUI charge. While in a cell in Pasadena, Dre was given special dispensation to shoot a music video with the late, great Tupac Shakur. Which is rather generous, isn’t it?

Vince Neil

In 1984, Motley Crue singer Vince Neil was drunk driving and hit another vehicle head-on. One passenger (Nicholas 'Razzle' Dingley) died and two others were severely injured. He pleaded guilty and got 30 days in jail. Why? Well, because he paid $2.5 million in 'restitution'.

20 years later, Neil admitted this in an interview: 'I wrote a $2.5 million check for vehicular manslaughter when Razzle died. I should have gone to prison. I definitely deserved to go to prison. But I did 30 days in jail and got laid and drank beer, because that’s the power of cash. That’s f**ked up.'

So what can we learn from the stretches of these famous inmates? Well, it seems fairly clear that celebrities are gifted very few separate and specific privileges once they’re inside. That said, of course, most are at an advantage from the beginning.

Their financial resources heighten the chances of a top drawer legal defence able to get them minimal sentences at more comfortable penitentiaries. Once you’re in, though? You’re just as likely to get a chicken burger thrown in your face as any other convict.

On the whole, it seems that prison life is slightly easier if you’re a ‘VIP’ guest. Provided you’re prepared to put your hand in your pocket. For your wallet, that is. Not a shank.