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Classic Hollywood Stars Who Served Time in Jail

You know what they say. If you do the crime, then you must do the time. While some super-rich, well-connected folks seem to be able to weasel their way out of legal repercussions for their questionable actions and behaviort. The average individual who commits some sort of crime will have to pay for their misdeeds. Celebrities might sometimes think that they are above the law – or at least they might act like it. But their high-profile status isn’t some kind of magical legal shield.

From Robert Michum to Tim Allen to Robert Downey Jr., literally dozens of stars have found themselves thrown into the slammer after breaking the law and getting caught – many times totally red-handed. Join Facts Verse as we take a look at a few classic Hollywood stars who have served time in jail.

Robert Mitchum

In the autumn of 1948, the star of such classic films as Night of the Hunter and Cape Fear was puffing away on a joint at a low-key party in the Laurel Canyon area of LA when law enforcement officers raided the place and arrested him.

At the time, Mitchum quoted as saying that his arrest would prove to be the ‘bitter end of everything’. He reportedly believed that he was about to lose his career, marriage, and everything else he had worked so hard to achieve. In reality however, it wouldn’t be as bad for him as he suspected.

Mitchum already separated from his wife, Dorothy, at the time, but they would get back together, and she would support him throughout the scandal.

As far as the public went, nobody seemed to care that he had caught smoking the ‘devils lettuce’. Mitchum’s career also didn’t seem to take a hit either. The next film that he appeared in, Rachel and the Stranger, ended up being a box-office success.

It’s speculated that Mitchum’s arrest largely meant to be a publicity stunt to show off the LA Police department’s anti-drug measures. When it came time for Mitchum to go to court, his expensive studio attorneys took issue with several irregularities in the case. But ultimately Robert agreed to serve 60 days in jail. Upon release, he spent the next three years on probation.

Mitchum died of complications of lung cancer on July 1, 1997. Join Facts Verse as we take a look at a few classic Hollywood stars who have served time in jail.

Mae West

The Roaring Twenties all about pushing the envelope of what considered socially acceptable, but not everyone was happy about this.

On February 9, 1927, Mae West was backstage at a performance of her controversial play ‘Sex’ when she found herself surrounded by cops from the NYPD Municipal Vice Squad who subsequently rounded her. And the play’s cast up and threw them in the back of black police vans.

West known for being a wide-cracking, silver-tongued, blond-bombshell during the Golden Age of Cinema. She was notorious for delivering some of the most risque and cutting one-liners in film history. Since she was both a screenwriter and playwright in addition to being an actress. She penned many of those suggestive lines herself.

West got her start in show business in burlesque before arriving in Tinsel Town. As she struggled to make a name for herself in Hollywood, she decided to make a pretty bold move by writing a provocative play in which she would take on the leading role as a sex worker.

She fully knew that her play ‘Sex’ would met with controversy. Even though the 20s were pretty wild, there was increasing censorship and scrutiny facing the entertainment industry. That being said, looking back on it, ‘Sex’ really didn’t even deserve the backlash it received. It was less about the act of sex itself and more about the power dynamics between the sexes.

On April 19, 1927, West charged with obscenity and ‘behavior designed to corrupt the morals of the youth’. She then sentenced to 10 days in a labor house.

She served her brief sentence on Welfare Island – which later renamed Roosevelt Island – in New York City. It’s even alleged that she had dinner with the warden during her stay. Citing her good behavior, West released two days early.

West would later say that her time in jail and the media attention she received because of it was well worth it. Humorously, she would quip that the only thing that bothered her about the experience was having to wear cotton panties. Join Facts Verse as we take a look at a few classic Hollywood stars who have served time in jail.

West passed away on September 18, 1980, shortly after suffering a stroke that left her paralyzed on her right side. Ultimately it was pneumonia that claimed her life.

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Lila Leeds

Best known for her films Lady in the Lake, April Showers Society Girl, Moonrise, and Wild Weed, Leeds was a relatively popular actress in the 1940s.

On September 1, 1948, she arrested alongside Robert Mitchum when the police raided the party they were both attending. She charged with marijuana possession and spent the next sixty days in jail.

Reportedly, Leeds introduced to heroin for the first time while she was serving time in jail.

She would later star in the Reefer Madness-style anti-cannabis propaganda film You Shoulda Said No in 1949. But unlike Mitchum, Leed’s career would never recover after the scandal.

Tim Allen

On October 2, 1978, the Home Improvement actor arrested at the Kalamazoo-Battle Creek International Airport in Michigan. He charged with possession of over 650 grams of cocaine.

Allen ended up pleading guilty to felony drug trafficking charges and gave police the name of other dealers in exchange for a reduced sentence. He was initially looking at a life sentence, but after snitching out his buddies. He slapped with a sentence of three to seven years in prison.

Allen paroled on the 12th of June 1981 after serving just two years and four months of his sentence.

In 1998, Allen arrested once again for DUI in Birmingham, Michigan. At the time of his arrest, he had a blood-alcohol level of .15 – almost twice the legal limit in the state of Michigan. He slapped with one-year probation and subsequently checked himself into rehab for alcohol abuse to fulfill a court-ordered obligation. Join Facts Verse as we take a look at a few classic Hollywood stars who have served time in jail.

James Brown

Known as the ‘Godfather of Soul’, this legendary singer had several run-ins with the long arm of the law during the summer months of 1988. But those would only result in him serving probation. But later that year on September 24, he went on a reckless and violent spree that resulted in him charged with assault and battery with the intent to kill.

That day, he walked into an insurance seminar in Augusta, Georgia, toting a shotgun and a pistol and ordered everyone to vacate the premises. He then ran off in his truck while attempting to evade the police. During the chase, the cops followed him into South Carolina and back to Georgia again.

He kept running even after police shot out three of his tires. After driving on wheel rims for six miles, he ended up crashing in a ditch.

Brown, who had earlier that year already charged with PCP possession and illegally carrying a pistol ended up sentenced to six years and six months in prison. Three years later, he released.

In 1998, Brown once again got himself into a bit of trouble when he arrested and charged with possession of weed. Fortunately for him, this time he did serve any time in the slammer. He did, however, have to enter into a 90-day drug treatment program.

In December of 2006, Brown died at the age of 73. Join Facts Verse as we take a look at a few classic Hollywood stars who have served time in jail.

Sean Penn

The I Am Sam star, Sean Penn, has gotten himself into legal trouble on more than one occasion.

In October 1985, Sean pled no contest to charges that he accosted two journalists who were trying to snap photos of him and his girlfriend at the time, Madonna, in Nashville, Tennessee. He ended up fined fifty bucks on each of his two assault and battery charges.

A year later, Penn charged with assault once again for attacking Leonel Borralho, a correspondent for a Hong Kong newspaper, after he discovered the man taking photographs of him and Madonna as they arrived at their hotel.

Several months later, Penn charged with battery an additional time for allegedly assaulting singer-songwriter David Wolinksi at a nightclub in Los Angeles.

Then in 1987, Penn violated the terms of his probation and arrested after he punched a film extra named Jeffrey Klein in the face while filming the movie Colors. He received a 60-day sentence in jail. Months later, he arrested for reckless driving and spent another 33 days in jail. Join Facts Verse as we take a look at a few classic Hollywood stars who have served time in jail.

Robert Downey Jr.

In the mid-90s, Downey Jr arrested numerous times on charges related to the possession of narcotics. He ended up going through several drug treatment programs and shockingly revealed to a judge in 1999 that he had addicted to drugs since he was 8 years old. He further asserted that it was his father who got him hooked in the first place.

In 1996, Downey Jr was arrested for possessing multiple illegal substances as well as an unloaded .357 Magnum handgun after he pulled over for speeding on Sunset Boulevard. A month later he was arrested again after trespassing into one of his neighbor’s homes. And falling asleep in one of their beds while under the influence of an illicit drug.

He given probation and ordered to undergo regular drug testing. After missing a mandatory court-ordered drug test in 1997, he spent six months in the LA County Jail.

In 1999, he missed another drug test and arrested yet again. He sentenced to three years in prison. A year into his sentence, Robert was unexpectedly freed after a judge granted him an early release. On thanksgiving in 2000, he was arrested after his hotel room was searched by police who found several illegal drugs.

Downey Jr would continue to struggle with addiction for the next year or so and would be admitted into another two rehab facilities. After five years of arrests, addiction, and relapses, he got clean and sober in 2001. And went on to have one of the greatest career comebacks in cinema history. Join Facts Verse as we take a look at a few classic Hollywood stars who have served time in jail.

Mark Wahlberg

Wahlberg has portrayed himself as a professional actor for about as long as we can remember but when when he was 16 years old he spent 45 days behind bars. He wound up there after assaulting a Vietnamese shopkeeper and using racial slurs against him. The night that the incident took place, Wahlberg was apparently under the influence of PCP.

Reflecting on his experience in jail years later, Mark admitted that it had changed his perspective on life and motivated him do better.

Well, that wraps up this video, but let us know if you can think of any other stars who have spent time in jail. Also, feel free to share your own experience with incarceration and how it changed your outlook on life.

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As always, thanks for watching! We’ll see you soon with more content covering some of your favorite Hollywood stars, films, and television shows. Take care.

Written by Alex Carson

Alex Carson is a seasoned writer and cultural historian with a passion for the vibrant and transformative decades of the 1960s and 1970s. With a background in journalism and a deep love for music, film, and politics, Alex brings a unique perspective to the ever-evolving landscape of entertainment.

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