Stars and Stripes: Celebrities Who’ve Been to Prison

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By: Isabel Sociedade | Last updated: Dec 06, 2022

It’s not all openings, galas, and designer clothes.  Being a celebrity may seem glamorous, but fame has its downsides. The darker side of celebrity goes beyond hounding by paparazzi, being asked for autographs, and being stopped in streets by people asking, “Aren’t you….?”

 

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Some of the rich and famous struggle with addiction, some with a hunger for more money, and some with their own violent alter egos. The stories of those who get caught and go to prison are both sad and cautionary.

Serious Fraud, Serious Jail Time

“Chrisley Knows Best” stars Todd and Julie Chrisley defrauded banks of tens of millions of dollars in the past few years. They cheated and stole their way to amass this fortune while at the same time evading payment of their federal income taxes. 

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The judge sentenced them to 12 years for Todd and 7 for Julie.  The FBI agent who worked on the case, Kent Farley, stated, “As this sentencing proves, when you lie, cheat, and steal, justice is blind to your fame, fortune, and position.”  Lesson learned?

In a Russian Jail for Nine Years

The recent case of WNBA star Brittney Griner has caught the attention of the sports world, and anyone else who travels frequently to countries with strict drug laws. Griner was arrested in February 2020 with some vape cartridges and hashish oil in her luggage when she was leaving Moscow.  Now that’s a very bad move.

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Imprisoned while awaiting trial, and while the US government did everything it could to free her, the Russian court declined all attempts to let her go and sentenced her in October to nine years in prison.

Making Friends in Prison

Danny Trejo was one of those criminals who could not stay out of prison for very long.  He had multiple offenses for drugs and theft in the 1960s, before he began his acting career.  Guess who he befriended in jail?  Charles Manson.

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Manson convinced Danny and his friends that he could hypnotize them to think they were high on drugs.  Trejo said it worked, and that Manson could have been a professional hypnotist. Trejo became a film star in the 1980s. Manson chose other work.

Addicted and Violent

Mark Wahlberg has a history of cocaine addiction. That addiction led to a violent encounter when he was 16. He attacked two Vietnamese men without provocation, battering one with a stick and punching the other while using numerous racial insults against the men during and after the beatings.

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He was convicted and charged with attempted murder, pleading guilty to assault. The judge sentenced him to two years in jail, but he only served 45 days. After that, he seemed to turn his life around.

Admissions of Guilt

Oh, what parents will do to get their kid into a good college. In 2019, Felicity Huffman and several other wealthy parents tried to influence college admissions staff at top universities to accept their children.

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The celebrities were convicted of conspiracy to influence the universities. The intense pressure for their children to attend certain universities led Huffman and others to use their fame and money to force the issue.

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Raise Her Score

Huffman admitted to paying someone to proctor and correct her daughter’s college board test, which resulted in the score jumping 400 points above her PSAT performance.

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Huffman was the first to be sentenced, told to serve 12 months of supervised release, do community service, and pay a fine.  After sentencing, she apologized to the students “who work hard every day to get into college.”

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Violent Movies or Violence Making a Movie?

As they say, “life imitates art.”  During the filming of the 1988 movie about gang wars, “Colors,”  star Sean Penn got into trouble by punching one of the extras.  

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Penn’s reputation has never been stellar.  He’s had violent outbursts on occasion, which the entertainment outlets publicized widely.  For this particular offense, he was sentenced to 60 days in jail.  By the way, at the time of this arrest, he was on probation for two other assaults.

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Drugs and Alcohol

Christian Slater punched his girlfriend in 1997 and then assaulted the police officer who came to the scene.  All of this took place while he was under the influence of drugs and alcohol.

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He blamed the incident on the heroin he was using.  It doesn’t seem that the judge felt much sympathy for that excuse since Slater was sentenced to three months in prison and then three months in rehab.

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Violence and Abuse

Chris Brown assaulted his girlfriend Rihanna in 2009. The story ran widely, with Rihanna providing vivid details of the entire night of abusive behavior.

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The judge sentenced Brown to five years probation, community service, and counseling and rehabilitation. That didn’t keep Brown in tow, however. In 2013 he violated his probation by getting kicked out of rehab and had to go to jail for several more months.

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Making More and More and More Money

For some celebrities, a boatload is not enough.  Often earning annual salaries in the millions, they feel compelled to hatch schemes to make even more. 

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In 2003 Martha Stewart, the household name synonymous with cooking, house decorating, and the wholesome life, was convicted of insider trading.

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Not the Wholesome Profile Any Longer?

Stewart was found guilty of four counts of obstruction of justice and lying to investigators. The judge sentenced her to five months of prison, five months of house arrest, and two years of probation. 

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Don’t worry yourselves, though. Unlike other celebrities who hang their heads in shame, or at least wait years for the public to trust them again. Stewart remains a beloved household icon for thousands of fans.  

It makes you wonder, doesn’t it?

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DUI for Mr. “24”

Drugs and alcohol do it again, this time for Kiefer Sutherland.  He was arrested in 2007 for driving under the influence.

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And it gets worse – at the time he was arrested, he was violating the terms of his probation for a previous charge. After serving his time, he took part in an alcohol education program for 18 months.  Let’s hope he learned something.

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Ironic Man

Here’s a celebrity who couldn’t keep out of trouble at the height of his addiction. Starting in 1996, he was arrested multiple times for drug violations, went in and out of rehab, and had several stints in jail.

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Eventually, he spent almost a year in prison after violating his parole. For someone who loved playing hero roles in movies, he disappointed his fams and himself by succumbing to addiction.

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Power 

Sometimes celebrities feel powerful, even invulnerable to bad press. It’s just not true. Mike Tyson spent three years in prison for the sexual assault of a 16-year-old girl in 1991. Tyson has always claimed that the sex was consensual. 

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The world-famous fighter was indicted by a grand jury in September 1991 and convicted in February 1992. In March, he began serving his term at the Indiana Youth Center near Plainfield, Indiana. He was released, after serving three years, in March 1995. He still maintains his innocence.

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Let’s Just Not Pay

We all grumble and groan at tax time, but most of us pay our taxes in good faith that it is our civic responsibility. Why can’t celebrities do the same?  For goodness sake, don’t they have enough money?

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In 2013 singer Laryn Hill was sentenced to three months in prison for not paying her taxes.  After serving her time, she released a song, “Consumerism.” Here’s betting that most of us pay our taxes and don’t write hit songs afterward.

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Beyond the Beyond

Tax fraud and fist fights seem tame compared to the story of Phil Spector.  The famous music producer worked with some of the greatest musicians of the 20th century, including the Beatles and Ike and Tina Turner.

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In 2009 he was convicted of the murder of actress Lana Clarkson. Spector claimed that the death was an “accidental suicide.” 

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The Producer and the Actress

Lana Clarkson was found dead in Spector’s mansion with a gunshot wound to the head. Spector’s driver, who was waiting outside, claimed that Spector walked out of his house with a gun in his hand, saying, “I think I killed somebody.”

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Spector’s defense team argued that Clarkson was depressed due to her failing career, and committed suicide. Despite these claims, Spector was convicted of murder and died in jail in January 2021.

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He Ended Up in Jail Anyway

Americans were riveted to their televisions; it’s all they talked about around the water cooler back in 1994. The 134-day televised trial of O.J. Simpson for the murder of his ex-wife Nicole Brown Simpson made media history.  

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The jury found Simpson innocent. 

Then in 2007 Simpson commandeered a robbery and kidnapping scheme to retrieve some of the memorabilia which he claimed had been stolen from him. The scheme earned him a sentence of 33 years in prison; he served nine years and was released in 2017.

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A Rough Decade or So

Lindsay Lohan struggled with addiction for many years. The entertainment news carried story after story of arrests, rehab, more arrests, failed relationships, and more addiction. It was a sad tale of a Hollywood darling.

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In 2007 she was charged with a DUI and sentenced to two weeks in jail for failing to attend mandatory alcohol-education classes.

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Another Tax Evader

What is it with wealthy stars and failing to pay taxes?  Do they simply forget? Do they think no one will notice?  Is their income so large, and the taxes due to the government so high, that they can’t imagine writing the check?

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Wesley Snipes took this evasion thing seriously  He didn’t pay taxes from 1994 to 2000.  This trick won him three years in prison, from 2010 to 2013. Seems that someone noticed.

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Not Quite Santa Claus

Actor Tim Allen, famous for his roles as Santa Claus and as a fun Dad in “Home Improvement,” has a shady past.  Hard to believe? Doesn’t he seem like the all-American great guy and friendly neighbor?

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Let’s go back to before the acting. In the late 1970s, he was a drug trafficker. He was caught with hundreds of kilos of cocaine at an airport and spent two and a half years behind bars.  He was released in 1981.

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50 Cent at 16

The famous Rapper 50 Cent has sold over 30 million albums worldwide and won many prestigious music and performance awards. In addition, he is a successful businessman.

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Yet as a young boy he had a difficult childhood, losing his mother at a young age, and trying to survive on the streets.  He has said he started dealing drugs in elementary school. By the age of 16, he was jailed for six months on drug charges and sent to a correctional facility for minors.

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The Wild Man

Watching James Brown perform, you witness frenetic energy and a love of music and dance. He was called the “Godfather of Soul” and was Number 1 on the music charts year after year.

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Yet addiction to drugs and involvement in the drug trade brought him serious trouble. He was on probation for drug offenses in 1988 when he went on a crime spree and refused to stop for the police during a high-speed chase. The court charged him with six and a half years in prison.

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Perjury

Rapper Lil’ Kim has sold more than 15 million albums and 30 million singles worldwide and is known as “Queen Bee,” with thousands of fans. But that didn’t stop her from lying to a grand jury. In 2001 her friend was involved in a shooting. When questioned by a federal grand jury, she lied about her friend’s involvement. 

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She was charged with three counts of conspiracy and one count of perjury for lying. The court sentenced her to a year in prison and ordered her to pay a $50,000 fine. She made the most of her time in prison, though, producing a reality series covering her sentence.

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Taxes Again, and Oh, a Gun

Walking around with an unauthorized weapon seems risky, right?  Rapper and actor Ja Rule didn’t think so – he was arrested for possession of an unauthorized gun in 2010.  Oh, and there’s more.

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While he was serving his sentence of two years in prison for weapons possession, he was sentenced to a further 28 months for not paying his taxes.

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Money, Fame, Violence

Tommy Lee, the famous drummer and founder of the band Motley Crue, assaulted his wife Pamela Anderson in 1998. He pleaded no contest to kicking Anderson while she was holding their son.

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For the assault, the court sentenced him to six months in prison. In addition to the jail sentence, Lee  had many legal troubles relating to his home and professional life. interestingly, later in his life, he became a supporter of animal rights. Go figure.

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Talented and Troubled

Tom Sizemore is best known for his role in the 1998 movie “Saving Private Ryan.” However, with his long history of drug and domestic violence arrests, he gained a reputation as a troubled man.

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At one point, when the authorities found methamphetamine on him, he was sentenced to 16 months in prison.  What made things worse was that by holding the drugs he was violating the probation of an earlier drug-related conviction.

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Choose Your Boyfriend Wisely

Indian actress Monica Bedi visited Portugal with her boyfriend in 2002.  Unfortunately, they used forged travel documents.  Even more unfortunate was the fact that her boyfriend is a known gangster and terrorist, Abu Salem.

  

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The couple was arrested and Bedi spent two years in a Portuguese prison. It is rumored that her gangster boyfriend is responsible for obtaining film roles for her using his influence.

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Not Quite Saved

Dustin Diamond was one of the stars of the popular TV series “Saved by the Bell.”  He and the rest of the cast were extremely popular and adored by teens.

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In 2016 he was involved in an incident in a bar and was found carrying a knife. The police charged him with disorderly conduct and with carrying a concealed weapon. He was sentenced to four months in prison.

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Drugs, Crime, Murder

Lillo Brancato Jr. scored several good acting gigs into the early 2000s, including roles in “The Sopranos” and in a Robert de Niro film.  But the actor struggled for years with addiction.

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In 2005, he and a friend broke into a house to steal prescription drugs. When an off-duty officer came to the scene, Brancato Jr.’s friend shot and killed the officer.  Brancato Jr. was sentenced to 10 years in jail for his role in the shooting.  That sounds like an episode of ‘The Sopranos’, but it’s real life.

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A Bad Situation

“Jersey Shore” is a unique reality program that follows the lives of eight housemates at a vacation home. One of the housemates is Mike ‘The Situation’ Sorrentino, who gained fame on and off the show as a media personality.

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In September 2014, Sorrentino was charged with tax fraud, for not paying taxes on $8.9 million.  In April 2017, further tax evasion charges were levied against Sorrentino and his brother. Sorrentino was sentenced to eight months in prison.  

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