15 Celebs You Didn't Know Spent A Night In Jail

Every day, all around the world, people get into trouble with the law. It can be as easy as running a red light, forgetting that your license is expired or even getting a little too intoxicated in public. All of these examples are surely something we’ve all done at one point in our lives; the only difference is that sometimes we get caught and sometimes we humbly cruise above the detection line.

So what makes the sentences we receive as everyday civilians any different than the sentences a celebrity receives? Money - the answer is always money. As we all unfortunately know, everyone has a price, and depending on how much you are willing to spend, you can usually get yourself out of any precarious situation. But where can we draw the line? Just because you are famous does not mean you should be able to escape the law. If you did the crime you do the time, right? Wrong.

If celebrities are famous for one thing, it’s getting out of trouble by name-dropping or cash-flashing. Sure, some of them have done some hard time, but their sentences were heavily reduced when compared to a middle or lower class worker.

Here is a list of celebrities who managed to escape their long sentences with their tails tucked between their legs:

15 Sir Paul McCartney


Sir Paul McCartney is considered a talented and genuine soul, but even the most peaceful person can be thrown into jail if they knowingly break the law. When it comes to the legend that is McCartney, let’s just say that he had a very short encounter with the inside of a jail cell. In 1980, McCartney was arrested at the Tokyo International Airport for trying to smuggle half a pound of marijuana into the country. As a consequence, the Wings’ tour was immediately cancelled and McCartney was taken to the Tokyo Narcotics Detention Center where he spent nine days in jail. The Beatles had been warned about trying to smuggle drugs into Tokyo, but McCartney later stated that “this stuff was too good to flush down the toilet,” and he decided to take his chances. Luckily for him, fame allowed him to slip through what would have been a seven-year sentence.

14 Frank Sinatra


Frank Sinatra’s musical career can be seen as timeless, but that’s not the only thing about him that can be considered so. Sinatra’s jail sentence only lasted a couple of hours back in 1938, when he was charged and arrested for seduction. Although seduction is no longer a crime, it was once taken very seriously in the state of New Jersey. Sinatra had seduced an unmarried woman by promising her they would get married after they consummated their relationship. However, Sinatra had no intentions of marrying this young lady, and therefore ruined her reputation and good standing. At the age of 23, Sinatra found himself in quite the predicament, but to his surprise, the case was dropped when the court caught wind that the woman in question was already married. Sinatra might have jumped for joy if his charge hadn’t been revised and then reinstated as adultery instead. The young singer spent a few hours in jail before paying his way out of it.

13 Shia LaBeouf


Most of us still remember Shia LaBeouf as the bratty little brother from the TV show Even Stevens, but it would be wise not to base this actor off the dorky and heroic roles he’s played. Although he may look like an innocent celebrity, he is actually a wild card, who has been incarcerated five times. LaBeouf might have started his acting career at a young age, but that’s not the only thing he started young. LaBeouf’s criminal portfolio started at the age of nine years old, when he shoplifted a pair of shoes and was detained for almost six hours. But that did not stop him from doing the same mistake twice, and at 11 years old he was held for another six hours for stealing a Game Boy. At 20 years old, LaBeouf spent two nights in jail for attempting to stab his neighbour. And if this wasn’t enough he spent another night in jail when he refused to leave a Walgreen’s and then another 25 hours behind bars for disrupting a Cabaret play in New York City.

12 Paris Hilton


It’s no secret that Paris Hilton is a party girl; the socialite has spent many reckless nights surrounding herself with drugs, alcohol and poor choices. It is also not surprising to know that the juridical system has let her off the hook countless times thanks to her last name and bank account figures. Although Hilton has spent some time in jail, it seems her sentences were often cut short or handled by greasy fingers. In 2007, Hilton was sentenced to 45 days in the slammer for having driven under the influence, but 23 days later she walked out a free woman. Afterwards, Hilton stated that her time spent behind bars had caused her to see a new light, and awoken in her a desire to become an accomplished humanitarian. However, it didn’t take long before Hilton returned to her bad habits, and she was once again arrested in 2010 for the possession of cocaine, a crime in which she spent one night in custody.

11 Matthew McConaughey

Matthew McConaughey is an American actor who kicked off his acting career by landing a role in the legendary movie Dazed and Confused. Although McConaughey might look like a goody-two-shoes, his record does pack a small amount of heat. In 1999, McConaughey spent nine hours in jail after being arrested in Austin, Texas. On what charges you might ask? Well, here’s where it gets complicated. McConaughey’s old neighbour had notified the police of loud noises coming from next door, and so like any police officer would do, he went to investigate the complaint. What that officer was no doubt shocked to find was a butt naked McConaughey loudly playing the bongos while another man clapped. After a quick search, the officer found that McConaughey was in possession of marijuana and drug paraphernalia, and arrested the naked bongo player without any mercy. If McConaughey learned one thing from this experience, it is to always shut the window when he feels a mood coming on.

10 Khloe Kardashian

Although many things can be said about Khloe Kardashian, being below the law is not one of them. In 2007, Kardashian was arrested under DUI charges and sentenced to three years of probation. In which she would have to register herself in an alcohol education class and complete her duty in roadside cleaning. However, for a diva like herself, this was not an option. Kardashian was once again arrested for violating her probation and a new sentence was drawn up, one which indicated that the youngest Kardashian would have to spend a total of 30 days in Lynwood jail. Coincidently, Lynwood is the same jail that cut Paris Hilton’s sentence short, and it appears to have a soft heart towards celebrities. And so to no surprise, Kardashian ended up spending a measly three hours in jail before she was released due to “overcrowding.”

9 Winona Ryder


When it comes to Winona Ryder, most of us would be surprised to find out that she even knows what crime is, but this dark eyed beauty does have skeletons of her own. Back in 2001, Ryder was arrested for shoplifting from Saks Fifth Avenue in Beverly Hills and although she did not get any jail time outside of her original arrest, she did not go unpunished. Ryder was sentenced to three years of supervised probation, 480 hours of community service, a mandatory counselling program and a hefty fine of $10,000. After Ryder completed this long list of obligations, the Beverly Hills Superior Court Judge Elden Fox reduced her probation and stated that her record would eventually not bear the marks of a felony shoplifter. Throughout all the chaos that was going through Ryder’s mind, she notably remained silent and simply carried out her sentence, eager to get the embarrassing ordeal behind her.

8 Lindsay Lohan


Lindsay Lohan will always be that hilarious actress we grew to love on-screen, but unfortunately your love for her will come to a complete halt when you see what she’s been up to off-screen. There’s no doubt that Lohan’s downward spiral should not be laughed at, as it is tragic to see what substance abuse can do to what was once an innocent human being (but after being arrested over 15 times, I’m sure we can find some leeway). Lohan takes the cake when it comes to celebrity arrests, not only does she find herself encumbered by court dates and community service on a monthly basis, but she has no desire to complete any of her obligations. Lohan has been arrested for drug possession, driving under the influence, driving on a suspended license while intoxicated, chasing people with her SUV, battery, missed court dates, breaking her probation guidelines and well, the list could go on forever. However, Lohan manages to escape the jail sentence almost every time, well except for that one time when she spent a whopping 84 minutes in Lynwood Jail.

7 Bill Murray

Back in 1970, Bill Murray was a 20 year old pre-med student at the Regis University in Denver, but that’s not all he was. You see, at this point in time Murray thought it would be a good idea to hide five bricks of marijuana in his luggage while attempting to board a flight at the O’Hare International Airport in Chicago, but sadly this proved to be a terrible idea. To make things worse, Murray aided in his own capture by not being able to keep his jokes to himself, and was immediately detained when an undercover agent overheard young Murray joking about having “two bombs hidden in his luggage.” When the federal agents looked through Murray’s suit case, instead of finding bombs, they found $20,000 dollars worth of pot. As a first time offender, Murray was not charged with any jail time, but he was held for hours and charged with five years of probation. Subsequently, Murray dropped out of Regis University before he could get kicked out, and became the awesome actor we love today.

6 Nicole Richie


Nicole Richie first became known back in 2003, when she and old best friend Paris Hilton co-starred together in their reality TV Show The Simple Life. From then on, both women became notorious for their party monster life styles and regular substance abuse. Unfortunately for Richie, the choices she made would undoubtedly lead her towards a life filled with incarcerations. In 2006, Richie was arrested for driving under the influence and spent three nights in jail. When the police officer pulled Richie over, he was surprised to find her in the passenger seat, ready to confess that she was driving under the influence of Vicodin and marijuana. Richie’s vehicle matched the description of a car that had reportedly been driving on the wrong side of the freeway, and although at the time of arrest Richie had turned her car around, she confessed to the crime before the officer could search her car and find any proof.

5 Michelle Rodriguez

Michelle Rodriguez was arrested back in 2006 for driving under the influence in Hawaii. The actress was in Hawaii filming the ABC TV show Lost when she was arrested and thrown into jail for the night. Following her arrest, Rodriguez issued an apology to the officer’s that arrested her and blamed her actions on the steroids she was taking due to her allergies. Rodriguez reportedly told the police officers ‘’I don’t belong here! Why don’t you put a gun to my head and shoot me!’’ Instead Rodriguez was given the choice of completing 240 hours of community service or spending five days in jail, in which she chose the latter. Rodriguez also stated that her reckless driving was due to her prior work on The Fast and The Furious, where she learned to drive in a particular manner. As a result, Rodriguez got her license suspended for 90 days and she agreed to take part in alcohol-abuse rehabilitation classes.

4 Woody Harrelson

Woody Harrelson is an American actor and activist who has been nominated twice for an Academic Award, he is also known for his good humour and pro-active tactics. Back in 1996, Harrelson had a run in with the law that most people, the jury included, thought to be rather ridiculous. In his plan to legalize the growth of hemp in the rural area of Kentucky, Harrelson was arrested for planting four seeds of hemp. The talented actor was challenging a state law, with hopes that a new law would be passed in its stead, a law that would allow farmers to plant crops of hemp and reap new profits. Unfortunately, his vision did not go as planned and he faced an arrest and charges instead. Harrelson’s actions could have landed him in prison for a year, but luckily he was only behind bars for a short amount of time before he was acquitted of his crimes. His plan to differentiate hemp and marijuana was not successful despite all his efforts.

3 Natasha Lyonne 


Natasha Lyonne has come a long way from playing the role of Jessica in American Pie, and although she is a well known actress, life hasn’t always been easy for this beautiful celeb. It seems, once upon a time, Lyonne gave Lindsay Lohan and Amanda Bynes a run for their money when it came do numerous arrests. Lyonne is currently taking on the role of Nicky on Orange Is the New Black, and some can say that she is the perfect match for the role. Much like her character, Lyonne has also paid her dues when it comes to drug addiction and crime. The OITNB actress has been arrested for driving under the influence, and spent one night in jail for mischief, trespassing and oddly enough, threatening to molest her neighbour’s dog. All this resulted in Lyonne being evicted from her apartment and spending time on the streets before she nearly died back in 2005.

2 Mischa Barton


Mischa Barton is best known for her lead role as Marissa on The OC, but she has since then built up quite the reputation. In 2007, one year after her character was killed off of The OC, Barton was arrested for driving under the influence. Apparently, Barton was pulled over for driving between the lines during the wee hours of the morning. The actress was then held for questioning over her charge, the officers later found out that she was driving without a license while under the influence of alcohol, marijuana and the use of a controlled substance. Barton spent seven hours in a West Hollywood jail, and was released the following morning after paying a bail of $10,000. Barton seems to have learned from her mistakes, and has not been to jail since this incident. The actress even stated how disappointed she was at herself for doing something like that in the first place.

1 Bruno Mars


Bruno Mars may sing like an angel but there’s a reason he’s been “locked out of heaven.” In 2010, Mars was arrested at the Hard Rock Hotel in Las Vegas for the possession of cocaine. Mars was first suspected by hotel security when he walked into the washroom and took a long time to come out. Afterwards he was detained by hotel security until the police came to retrieve him. Mars spent numerous hours in the holding cell of the County jail and was then released with a court date, where he later pleaded guilty on his cocaine charges. In the end, Mars was sentenced to a year of probation, drug counselling and a $2,000 fine. The judge agreed to a plea deal and told Mars that if he followed through with his sentence, the charge would be erased from his record.

Sources: EOnline, FOXNews, People, HighTimes, UltimateClassicRock, CBSNews

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15 Celebs You Didn't Know Spent A Night In Jail