15 Hollywood Ladies Who Have Been Jailbirds

There’s something about the word ex-con that makes you think of a male figure. A menacing thug, a svelte Mafioso, a rugged drug dealer, a suave con man, right? But with women having reached the stars, literally, why should jail be filled with just men? So here are 15 women, and 15 Hollywood celebs at that, who paved the way for women to go behind bars too. Mostly, their offenses have been not so serious – I mean there are no murderesses or rapistas (is that a word?) in these.

But these 15 are all pretty little liars for sure. They have lied, cheated, stolen, drugged themselves to the hilt and driven all about town in a fogged state, narrowly missing painting the town red with blood with their hit and run misses. And since they are celebrities, frankly the law has been pretty lenient with some of them, letting them walk with a next to nothing sentence that has probably only fueled their devilish attitudes.

These are bad dudettes, and give celebrities a bad name on the whole. For these gals, the law is just another thing to be broken. Probably their brains have turned to mush with years of drug and alcohol abuse. Many of them are still very much on the scene, continuing their nutty lifestyle and adding to their toilet paper roll rap sheets. Still, others have come to their senses and tried to live a cleaner life. But as the cops say, once a convict – well, you can fill in the rest. Here are the female D-Bags of Hollywood who are nutty AF, and cannot seem to lead a jail-free life.


15 Stephanie Pratt: Prattling About Her Past

Stephanie Pratt sort of shot into the limelight since her brother Spencer was dating Heidi Montag and became the star of the reality TV series The Hills. Later Stephanie too became a main lead of the show. She’s been on other reality TV series as well including Celebrity Big Brother and Celebs Go Dating. That said, her personal life abounds with legal troubles as well as addiction issues. During her stint with The Hills, she suffered from bulimia, likely caused by the complex she had because of her thin-framed co-stars. In her autobiography, she mentions that she was hooked on crystal meth since she was 14 and it was her arrest in 2006 in Hawaii for shoplifting that finally made her change her life around and made her enter rehab. Even then, she was arrested for a DUI in 2009 though released on bail soon after. Since then she’s kept her nose clean, literally.

14 Paris Hilton: Playing Fast And Loose To The Hilt


So other than being an heiress and releasing a sex tape, Paris Hilton is also an ex-con! Perhaps not enough attention was being paid to her at home, or not enough likes on her social media, whatever the reason, Paris did a stint as a bad, bad girl. In 2006 she was arrested in LA for suspicion of DUI and she pled no contest to the same, being her first offense, she was merely put on probation. Then she violated her probation and was awarded a 45-day jail sentence as part of legal tough love. She served only 23 days and was released early due to, well, overcrowding. Not particularly repentant, Paris was caught on a marijuana possession charge in South Africa but she was an heiress, so another girl took the fall for her. In 2010, she pled guilty to yet another cocaine charge. She’s free nowadays but hey, with Paris, who knows?

13 Martha Stewart: The “Granny” Convict

Think Martha Stewart and you think grandmotherly cooking lady, right? Well, this daytime talk show host, TV chef, and kitchen appliance guru has also been a jailbird. Known for her difficult attitude at work, she unwisely decided to sell her stock in ImClone Systems after receiving an anonymous tip predicting its downfall. And rightly so, ImClone Systems fell by 16% the next day! She sold a total of 3,928 shares for more than $45000… Unfortunately, that is illegal and called “insider trading.” Add to that, when she was questioned about this by the authorities, she lied and obfuscated evidence. Duly arrested, she was held guilty of felony charges that included conspiracy, obstruction of justice, and lying to the federal investigators. And so she served five months in federal prison and two years of supervised release including five months of electronic monitoring. Oh and while in prison, she was called M. Diddy by the other inmates!

12 Carmen Electra: When Loss Drives You Nuts


Carmen Electra started her dancing career in a show called It’s Magic but then she was known by her real name, Tara Leigh Patrick. She then had a very short-lived music career with Prince’s Paisley Park Records and officially became Carmen Electra. By 1995, she became a TV regular as well as a Playboy regular and then got the role of her life as Lani in Baywatch from 1997 to 1998. More nondescript movie roles followed but her popularity as a model and the face of many brands soared. Trouble began when her mother and sister died within weeks of each other in 1998. Numb with grief, Carmen married NBA star Dennis Rodman in the Little Chapel of Flowers in Las Vegas. After just a few days they got their marriage annulled but got back together soon after. In 1999, Carmen Electra was arrested by Miami police for battering her then husband. Good sense prevailed and the charges were dropped, but marriage died soon after, albeit amicably.

11 Jane Fonda: Innocence Has No Fear

Jane Fonda is a powerhouse performer, and even if the millennials don’t remember her young and sexy roles way back when the Vietnam War was still on, you may remember her as the mother-in-law to be in JLo’s romcom Monster-in-Law! This actress was arrested way back in 1970 at the Cleveland airport on drug possession charges. Her mugshot shows her with a fist raised and a defiant expression and that distinctive haircut, for she had just finished working on Klute.

The arrest came after customs officials found pills labeled "b, l and d" in her bag which Fonda explained to them were vitamins for breakfast, lunch, and dinner. Her explanation fell on deaf ears and she was arrested willy-nilly, more for her anti-Vietnam political activism than on “actual” charges. Fonda later recounted, “They confiscated (my vitamins) as well as my address book (which was photocopied) and arrested me for drug smuggling. I think they hoped this scandal would cause the college speeches to be cancelled and ruin my respectability. I was released on bond and months later, after every pill had been tested in a lab (with taxpayer’s money!) the charges were dismissed and there were a few paragraphs hidden in the back of papers that they were vitamins, not drugs!”

10 Fiona Apple: Fallen Closer To The Tree


Fiona Apple has not led an easy life. Born to a singer mother and an actor father who never married and then split up when she was four, she was raped when she was 12 at knife point by a stranger just outside her mother’s apartment, in the corridor. She has carried those memories of her crying and stabbing the cupboard with a knife, as she tried to cope with her attack and loss, and now she wears them as badges.

She was arrested in 2012 in Texas on drug possession charges as she was found with .01gm of marijuana and .01gm of hashish. Fiona did go on a rant afterward once she got free on a $10000 bail about illegal and inappropriate conduct while she was in jail, though she never really cleared up the issue per se. Of course, she’s also the one who said this as an acceptance speech at the 1997 MTC Music Awards: “This world is bullshit, and you shouldn’t model your life on what we think is cool, and what we’re wearing and what we’re saying.”

9 Tawny Kitaen: Inner Heat Or Was It Rage?

So with a name like Tawny Kitaen, the woman has to have somewhat of a steamy past, right? While she began her acting career in 1983 with a minor role in the TV movie Malibu and then sort of yanked the spotlight on herself the next year by starring as the main character Gwendoline, in the erotic-adventure movie The Perils of Gwendoline in the Land of the Yik-Yak. She even managed to play the bride-to-be in Tom HanksBachelor Party and the lead in the horror movie Witchboard. Her personal life was rocky, though – she was briefly married to Whitesnake’s lead singer David Coverdale but had an affair with OJ Simpson while he was married to the Nicole Brown (and we know how that ends).

After Tawny and David divorced, she married professional baseball player Chuck Finley and the couple had two daughters over five years. In 2002, she was charged with domestic violence against her husband and they subsequently divorced. In 2006, she was charged with cocaine possession and had to enter rehab as part of the plea deal. In 2009, she was arrested for DUI. Looks like Tawny really loves to be behind bars!


8 Piper Kerman: When Orange Became The New Black


So for those of you who don’t know who Piper Kerman is, she became famous after her stint in prison when she wrote a book about her experience... oh and Orange is the New Black is based on her life behind bars. Piper Kerman was born to an affluent family of many doctors, lawyers, and educators and graduated from equally influential schools. For some reason, when Piper was 24, she got romantically involved with Catherine Cleary Wolters, a heroin dealer working for a Nigerian kingpin. Such was this love that Piper began to launder money for this drug operation and was consequentially caught in 1998 and indicted for the same. Piper pleaded guilty and served 13 months of her 15-month sentence at the minimum security FCI Danbury prison. Since then, her memoirs have turned into a series; Piper has become even richer and has been leading a straight-laced exemplary life advocating prison reform.

7 Lauryn Hill: The Misdirection Of A Great Singer

Lauryn Hill was on her way to greatness with her solo album The Miseducation of Lauryn Hill, and even before when she was part of the band Fugees with Pras Michael and Wyclef Jean. Her solo album became such a chart topper and unprecedented success that Lauryn simply quit the music world, supposedly after being disillusioned with the greed and connivance of it all. In the next few years, she proceeded to have six children, five of whom were fathered by Rohan Marley (Bob Marley’s son). In 2012, Lauryn was arrested for tax evasion and she pled guilty – she was convicted and ordered to pay back the taxes she had evaded from 2005-2007 during which she had continued to receive royalties for her music and made income touring as well. When she failed to pay the same back within the stipulated time, she was sentenced to three months in prison and three under house arrest, by a far a lenient sentence for the judge took into consideration her six minor children!

6 Khloe Kardashian: Just Try And Keep Up With Her


She’s the naughty sister on Keeping Up With The Kardashians and her bad girl image is not just limited to just the reality show. In fact, when she was young and had just gotten her license, she sort of took her mom’s car to a party without permission where for some reason the car caught fire and Khloe was in heaps of trouble! Legally, though, she was arrested in 2007 for DUI. She was released on probation but ended up violating it and surrendered to serve jail time, which could have been up to 30 days as per law. Khloe served just three hours (WTF!) and was released “early” because of overcrowding. She did enroll in an alcohol treatment program, though, soon after. In 2011, she was embroiled in a controversy when a transgender woman named Chantal Spears claimed that Khloe and her entourage brutally attacked her outside a nightclub. Khloe claimed it was self-defense and since this was a civil suit, no arrests were made.

5 Michelle Rodriguez: A Tough Girl Gone Nutty

It looks like her tough act in Girl Fight and The Fast & The Furious franchise have kinda gone to her head, and she certainly looks the part. Michelle was arrested in 2004 for DUI, and to top it off, was driving with a suspended license, which in turn had happened due to previous traffic violations. In May 2006, she violated her probation from another drunk driving charge and was awarded a 60-day prison sentence because by that time, the judge had probably had enough of her and her driving problems. Hilariously, she served only 4 hours and 20 minutes of her sentence and was released early because of, you know it... Overcrowding! That didn’t quite put a dent on her lack of driving skills, or rather, drinking and driving skills and in January 2008 she was back in business. So was the judge, who handed her a mandatory six month jail sentence, this time taking into account her innumerable traffic violations. This time too, she went free after serving just 18 days – the excuse being overcrowding again! Better swear off the booze Michelle, lest your luck runs out...

4 Lil' Kim: A Not So Little Sentence


So long before Nicki Minaj humped the screen and gyrated onto the rap scene, there was Lil' Kim, not little at all in the rap world. One of the biggest female rappers to date, Lil' Kim probably took those gangsta lyrics to heart a little too much. In 2005, she was put on the witness stand when her entourage was involved in a gangster shooting in front of the hip-hop playing Hot 97 radio station. The shooters sort of forgot about the security cameras that recorded Kim’s manager and a friend trading shots with rival rap group Capone-N-Noreaga after a record called "Bang-Bang" which dissed Lil' Kim. Luckily no one was killed during this firing, though one person was wounded. She lied about this shooting or her entourage’s involvement in this but the prosecution proved otherwise and this non-snitching attitude of hers landed her a year and a day in jail. She served a full term and is back on the street, doing her Big Momma Thang the Queen Bee way!

3 Amanda Bynes: The Imaginarium Of A Mind Gone To Rot

The last we saw of Amanda Bynes the actress was way back in 2010 in the movie Easy A. And the last we heard of her, in a legal trouble sort of way, was in 2014. Things have been quiet since and frankly, we are thankful, because she is one troubled soul that needs all the help as well as peace and quiet that she can get!

She rose to fame in the shows All That and The Amanda Show on Nick. But from 2012, she’s been in the spotlight for all the wrong reasons. Many DUIs, a couple of hit and runs (which were settled out of court with Amanda paying compensation to the victims), driving on a suspended license… The times she has been held behind bars are many. In 2013, she was arrested for drug possession, reckless endangerment as well as tampering with evidence. A psychiatric evaluation and dropped charges later, she started a fire in someone’s driveway and was placed on psychiatric hold. Later she took to Twitter saying she was sexually abused by her father and then recanted saying he had planted a microchip in her brain that made her say this. More than jail time, this troubled celeb needs serious psychiatric care.

2 Cheryl Cole: One Cold Cherie Indeed


She's best known for winning a place in the UK girl group Girls Aloud as well as for her solo hits; "Fight for This Love," "Promise This," "Call My Name," "Crazy Stupid Love," and "I Don't Care" all reached number one on the UK singles charts making Cheryl the first British female artist to have five number ones in the UK. She has also appeared in the UK X-Factor as a judge in four seasons, and her ex-husband is footballer Ashley Cole, though she is currently dating One Direction singer Liam Payne with whom she also just had a son.

In 2003, she was involved in an altercation with a nightclub toilet attendant. A very drunk Cheryl took some sweets and lollies from the bathroom without leaving the customary tip. When the nightclub attendant Sophie Amogbokpa asked for her tip, Cheryl sort of went into a rampage calling Sophie a “black b*tch” and punching her in the face. Cheryl was detained and then a judge asked her to pay £500 to the victim as restitution as well as sentenced to 120 hours of community service, though racial charges were dropped.

1 Lindsay Lohan: You Don’t Mess With The Lohan

Frankly, she was the cutest little redhead we ever saw on our screens when she first appeared in The Parent Trap. Other rom coms came and went as she blossomed into more woman and less girl but as her years grew, so did her rap sheet. It started with a DUI and cocaine possession in 2007, and so it was rehab for her. After rehab, she repeated the offense and was sentenced to a day in jail but released in just about an hour. Then there was the theft of a Masha Markova fur coat which was “mysteriously” returned in 2008 but then in 2010, $400,000 worth of Dior jewelry went missing. Lohan was ordered to wear a SCRAM alcohol monitoring device. Being Lohan, she set it off at the MTV Movie Awards and so went to jail. The sentence was 90 days but she was released in just two weeks, and then she left her 90-day rehab early too. Too much, too soon, too far Lohan. We're bored now...

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