The justice system isn't always applied equally, and that's especially true if your starpower
lets you slip out of prison in mere minutes (right, LiLo?).
Which Oscar winner barely zipped-up their prison-issue jumpsuit before they were back
on the streets?
Keep watching to find out.
In the early years of the Kardashian media empire, Khloé Kardashian was arrested for
driving under the influence in 2007.
She then appeared on "The Tyra Show" and claimed she was glad no one was hurt or killed, adding,
"What I could have done is just unthinkable.
I will never, ever do that again."
"Guess who's going to jail on the 18th!"
But she missed her court-mandated alcohol education classes, and she skipped out on
her road-cleanup community service, meaning she had to go to prison as a result.
The Season 3 premiere of "Keeping Up With the Kardashians" dutifully captured all the
drama of the moment, as older sister Kim wouldn't stop snapping selfies.
Of course, that led to one of the most iconic lines of the entire series.
"Kim, would you stop taking pictures of yourself?
Your sister is going to jail."
At the time, a rep for Khloe told People magazine,
"Khloé is ready and willing to serve out her sentence, no matter how long and where,
and have this resolved."
But even though she was sentenced to 30 days behind bars for the probation violation, she
ultimately served a whopping three hours, due to overcrowding.
Years later, it seems the famous family hasn't let Khloe forget her brief time as a jailbird.
According to US Weekly, it appears that both Kim and Kris have Khloé's mugshot displayed
prominently in their homes.
Before he was the star of the '90s mega-hits "Home Improvement" and "Toy Story," Tim Allen
was just a normal stand-up comic — who got arrested for being in possession of more than
a pound of cocaine, in 1978.
According to CBS, Allen cooperated with investigators, voluntarily giving up the names of other drug
dealers in order to get his sentence reduced.
He told the Los Angeles Times,
"I pleaded guilty.
I knew what I did was wrong, I did not drag it out in a trial.
I laid down.
Punish me."
"Got myself in trouble, ended up doing some prison time, humiliated my family, and all
of it was selfish."
Though he was ultimately sentenced to 3 to 7 years in prison, he was granted parole a
little over two years later.
During a sit-down with Marc Maron, Allen reflected on his time in the big house, recalling,
"I learned literally how to live day by day.
And I learned how to shut up.
You definitely want to learn how to shut up."
He also elaborated on how his run-in with the law helped him turn his life around — and
ultimately become a major Hollywood star.
As he told Closer Weekly,
"It was a watershed moment.
It put me in a position of great humility, and I was able to make amends to friends and
family and refocus my life on setting and achieving goals."
Former child star Lindsay Lohan has repeatedly lucked out when it comes to having her jail
time reduced.
Her initial stint in the clink — the result of drunk-driving charges and possession of
cocaine — was supposed to be one day long.
But she only served 84 minutes of the sentence, because of overcrowding.
In advance of serving her time, she confessed to the Associated Press,
"It is clear to me that my life has become completely unmanageable because I am addicted
to alcohol and drugs."
"It was like a party thing.
People would have it and I would do it."
Then, in 2010, Lohan was sentenced to 90 days in jail for violating probation after she
skipped the alcohol counseling sessions she had been ordered to complete, according to
CNN.
The Guardian reported that she was initially placed in solitary confinement, and was ultimately
released early for good behavior, on account of overcrowding.
She had served just 14 days of the three-month sentence.
She was later sentenced to 120 days in jail for the much-publicized theft of a necklace,
but according to Reuters, she was allowed to serve just 35 days under house arrest,
instead.
The Hollywood Reporter noted that she used her time at home to film an ad for Beezid.com,
quipping:
"Hey to all my friends.
I just want to share with you that during some of my time at home, I found this amazing
site with great deals."
After numerous run-ins with the law throughout the '90s, actor Robert Downey Jr. told a judge
he wanted to get sober despite repeatedly violating a court order to submit to regular
drug testing.
Describing exactly why he couldn't seem to get clean, he said,
"It's like I've got a shotgun in my mouth, my finger on the trigger and I like the taste
of gun metal."
According to the Los Angeles Times, he was sentenced to three years in prison in an attempt
to ensure his pending sobriety.
But he was released less than a year later.
As CNN reported, an appeals court had noted that the sentencing judge failed to clarify
whether his penalties would be served consecutively or concurrently.
The Deputy Attorney General explained to the Los Angeles Times,
"People talk about [how] you get loose on a technicality.
This is one of those."
"My name is Tony Stark and I'm not afraid of you."
Marvel took a chance on the actor when it tapped him for 2008's "Iron Man," and the
rest is mega-budget franchise history.
He later opened up about his previous crimes and struggle with addiction, telling Vanity
Fair,
"​​Job one is get out of that cave.
A lot of people do get out but don't change.
So the thing is to get out and recognize the significance of that aggressive denial of
your fate, come through the crucible forged into a stronger metal.
Or whatever."
Paris Hilton has quite the resume: hotel heiress, reality TV pioneer, actor in underrated films
like "House of Wax," and singer behind the modern classic pop song "Stars Are Blind."
But in the late 2000s, at the height of her cultural power, she added another moniker
to her multi-hyphenate resumé: jailbird.
Hilton ran afoul of the law thanks to her hard-partying lifestyle finally catching up
to her.
She was arrested in 2006 on suspicion of drunk driving, and as a result, she lost her license.
The following year, though, she was arrested again, this time for continuing to drive on
said suspended license.
Claiming she didn't realize her misstep, she declared to the court,
"From now on I want to pay complete attention to everything."
But that wasn't a good enough excuse, and the star was sentenced to 45 days in lockup,
according to Reuters.
Her mom Kathy Hilton reportedly shouted, quote, "You're pathetic!"
at the judge who locked Paris up.
"It was just very cruel and very mean."
But, all things considered, Hilton ultimately served only five days in prison before being
released.
According to the East Bay Times, the decision to move her from prison to house arrest was
due to a medical issue.
And the specifics were never released to the public.
Of all the socialites who went to jail in the 2000s, Nicole Richie got off the easiest.
In 2006, the star of "The Simple Life" was arrested on suspicion of driving under the
influence of drugs after her Mercedes was seen going the wrong way on a freeway.
When cops arrived, her car was fully stopped in the carpool lane.
According to the California Highway Patrol, Richie admitted she had used Vicodin and marijuana
before getting in the car.
While a previous arrest for possession of heroin had led to a court-mandated rehab stint,
this time Richie was sentenced to hard time.
She pleaded guilty to charges of driving under the influence of drugs, and the judge gave
her four days in jail, according to the AP.
Despite all that, Richie lucked out.
Because of serious overcrowding, she was ultimately made to serve only 82 minutes of her sentence.
The L.A. County Sheriff's Department told The Hollywood Reporter,
"She was processed into the jail system, she was highly cooperative and she was released."
"I really don't have any regrets in life, even the mistakes, the drugs, everything,
because it made me who I am today."
Though it's become a rite of passage for the Bravo franchise to feature Housewives with
legal issues, "Real Housewives of New Jersey" star Teresa Giudice was the first to go to
jail for her crimes.
She was sentenced to 15 months in prison after pleading guilty to multiple counts of fraud
— despite claiming that she didn't know what she was signing when she put her name
on the documents.
As she told Andy Cohen,
"I've had sleepless nights.
Of course, I was shocked.
It was very unexpected.
I don't even know what to say."
"I was fine not wearing makeup everyday.
I just missed my daughters."
Though she reported to prison in January 2015, Giudice was out in time for Christmas, ultimately
serving only 11 months of her 15-month sentence.
But the table-flipping reality star denied that she had received preferential treatment
while serving her time.
She explained to "Good Morning America,"
"I mean, there was mold in the bathrooms.
There was not running water constantly.
The showers were freezing cold.
It was hell.
It was definitely living in hell."
At the age of 16, long before the Calvin Klein ads and the action movies, Mark Wahlberg committed
some serious crimes.
According to The Smoking Gun, he once harassed a group of Black children and beat a Vietnamese
man.
Arrest docs show that, in addition to using racist slurs against the victims, he told
police officers,
"You don't have to let him identify me, I'll tell you now that's the motherf—er whose
head I split open."
"I'm a good liar.
I'm a born liar."
As the Daily Mail reported, Wahlberg was sentenced to two years in prison, but served only 45
days for his crime.
Years later, in 2007, Wahlberg told ABC News that he no longer lingers on that chapter
in his life.
He said,
"I did a lot of things that I regretted and I certainly paid for my mistakes.
You have to go and ask for forgiveness and it wasn't until I really started doing good
and doing right, by other people as well as myself, that I really started to feel that
guilt go away."
Although Johnny Trinh, the man whom the actor assaulted, told the Daily Mail he never knew
his attacker was in fact Mark Wahlberg, Trinh publicly forgave him, adding,
"He was young and reckless but I forgive him now.
Everyone deserves another chance."
Though he was later found liable in a civil court for causing the death of Nicole Brown
Simpson and Ron Goldman, we all know OJ Simpson avoided serious jail time when he was found
not guilty of murder.
But he was later arrested on numerous charges relating to the theft of his sports memorabilia.
Simpson claimed he was simply taking back what was already his, but the police disagreed.
When the Associated Press asked him why he hadn't called the cops to retrieve the items,
Simpson said,
"The police, since my trouble, have not worked out for me."
Thirteen years after he was acquitted of murder, Simpson was sentenced to 33 years in prison,
according to Reuters.
He said at the time,
"I didn't mean to hurt anybody, and I didn't mean to steal anything."
The father of murder victim Ron Goldman was happy with the sentence, even though it was
unrelated to his son's death.
He told NBC News,
"We are thrilled, and it's a bittersweet moment.
It was satisfying seeing him in shackles like he belongs."
Still, nine years into his 33-year sentence, Simpson was released on parole, in the middle
of the night, telling news cameras just hours after his release,
"Please, can I have a break here?
God bless, take care."
Rapper Meek Mill was "in and out of" the Philadelphia court system for more than a decade on charges
related to gun possession back in 2008, according to Rolling Stone.
But in 2017, a judge ultimately sentenced him to 2 to 4 years in prison for probation
violations, against the advice of prosecutors.
The arbitrary nature of the sentencing quickly drew widespread condemnation.
As CNN noted, his "violations" included things like riding a motorcycle without a helmet
and popping wheelies.
Not typically the sort of things to earn serious jail time.
Numerous hip-hop stars called for his release, including Jay-Z.
In the documentary "Free Meek," Jay noted that Mill's story represented more than just
the one situation — and spoke to something seriously wrong with the legal system.
He explained,
"Meek is not the only one.
You tell people these stories — you can't believe it, until you hear it from a source
and [then] it's like, this is not fantasy.
This is fact."
"Give up for Meek Mill and welcome home!"
Ultimately, CNN reported that Mill was released five months into his 2 to 4 year sentence,
thanks to an order from the Pennsylvania Supreme Court.
The rapper said in a statement,
"While the past five months have been a nightmare, the prayers, visits, calls, letters and rallies
have helped me stay positive."
Mill and Jay-Z have since launched a criminal justice reform organization together.
"Desperate Housewives" star Felicity Huffman was arrested in 2019 when she got caught up
in the notorious College Admissions Scandal.
She was accused of paying $15,000 to have a proctor help her daughter cheat on the S.A.T.'s
by giving her more time to take the test and fixing incorrect answers.
Huffman pleaded guilty and admitted in a statement,
"I am ashamed of the pain I have caused my daughter, my family, my friends, my colleagues
and the educational community."
She was sentenced to 13 days in jail for the offense.
But USA Today reported that she ultimately served 11 days of her two-week sentence.
And it seems that a simple processing routine is the cause for her early release.
For prisoners whose sentences would have been up on a weekend, the jail releases people
on a Friday instead.
Huffman has kept a low profile since her time in lockup.
And as a source told E! News,
"She is incredibly relieved that she has served her jail time and is moving ahead with her
life."
Though he has since turned his image around and become a director, philanthropist, and
an Academy Award-winner, back in the '80s, a young Sean Penn was a bad boy.
The tabloid fixture was even arrested in Macau in '86 for holding a photographer out over
a balcony on the ninth floor of a hotel.
And according to the Sydney Morning Herald, he once told a biographer that he and his
assistant escaped from jail.
"Hey, bud, let's party!"
But in 1987, Penn ran into his biggest legal trouble yet.
Following a string of violent incidents, including reckless driving and brutally beating an extra
on the set of "Colors," the Los Angeles Times reported that Penn had been sentenced to 60
days in prison.
He served only 32 days before being released, with the Associated Press reporting it was
due to good behavior.
According to The Hollywood Reporter, Penn revealed decades later that he had corresponded
with fellow inmate Richard Ramirez — the serial killer known as "The Night Stalker"
— while in jail.
An officer had reportedly told Penn that Ramirez was a fan.
And after receiving a note from the Night Stalker that included a pentagram and a sketch
of Satan, Penn wrote a reply that read,
"You know, Richard, it's impossible to be incarcerated and not feel a certain kinship
with your fellow inmates.
Well, Richard, I've done the impossible, I feel absolutely no kinship with you."
Controversial rapper Tekashi 6ix9ine has been dogged by legal trouble for his entire career.
In 2015, the rainbow-haired artist behind hits like "GUMMO" and "FEFE," pleaded guilty
to charges of using a child in an explicit performance.
As Pitchfork reported, in 2018, he was sentenced to four years of probation instead of jail
time.
Later that same year, TMZ broke the news that Tekashi had been arrested on racketeering
and firearms charges related to his alleged involvement in the gang known as the Nine
Trey Bloods.
He fully cooperated with the investigation, giving up the names of other gang members,
in order to avoid a possible life sentence.
He said in a statement, via the Inner City Press,
"I know God has a bigger plan for me.
I want to inspire the youth that it's never too late to change."
"I don't wanna be a superhero.
I wanna be like, I wanna be a villain.
Villains never die.
Superheroes always die."
The jail time he had already served counted toward his two-year sentence, but he was released
several months early anyway.
According to the judge who released him,
"COVID-19 presents a heightened risk for incarcerated defendants like [Tekashi] with respiratory
ailments such as asthma."
On Instagram Live shortly after his release, Tekashi said,
"You know why people [are] so mad?
Cause they thought it was over for me.
They counted me out.
Y'all could never cooperate with the government and come back.
I'm a living legend."
In 2014, comedian Hannibal Buress ignited a firestorm when he called out Bill Cosby
onstage for assault allegations that had amounted against him over the years.
His efforts to bring awareness to the situation effectively got the ball rolling.
And in 2015, 35 women who say Cosby assaulted them appeared on the cover of New York Magazine.
In 2018, Cosby was sentenced to 3 to 10 years in prison after being convicted of sexual
assault.
A year later, he told Black Press USA that he expected to serve his full sentence because
he would not be apologizing.
He said,
"I have eight years and nine months left.
When I come up for parole, they're not going to hear me say that I have remorse."
But in 2021, his conviction was overturned, and he was released early.
A prosecutor had reportedly told Cosby he wouldn't be charged, and the Pennsylvania
Supreme Court decided it was unfair that Cosby was later charged anyway.
After getting out, Cosby tweeted,
"I have never changed my stance nor my story.
I have always maintained my innocence.
Thank you to all my fans, supporters and friends who stood by me through this ordeal."
If you or anyone you know has been a victim of sexual assault, help is available.
Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline
at 1-800-656-HOPE (4673).