The life of the rich and famous may be glamorous, but money can’t buy you innocence. More celebrities have been arrested than you can imagine, and the famous culprits on this list are no strangers to handcuffs. From the infamous Lindsay Lohan, who was charged on four separate crimes in two different states across the country in the short time span of just a few months, to the murder trial of former hero athlete O. J. Simpson, these famous stars have been in the news more times for their bad behavior than they’ve been recognized for their celebrity appeal or talent.
So what exactly happened to some of your favorite bad boys and girls from the entertainment industry, and where are they now? Read on to find out…cause the singers, actors, athletes, and other famous stars on this list are proof that good looks and fame don’t necessarily equal a life worth envying. From fights, to drug charges, to legendary stars accused of murder the celebrities in these photos are infamous for having it all, and throwing their careers away because they just couldn’t handle their rise to fame and fortune. Not to mention the fact that a middle of the night DUI arrest doesn’t always make for the sexiest mugshot photo on the next morning’s front page. Here in the list below are some of the best f*!k-ups from your favorite stars who have more arrests than awards!
15. Lindsay Lohan – From Queen Of Child Stars To Behind Bars
No list of fallen celebrities would be complete without the poster child of train wrecks, Lindsay Lohan. Lindsay first came onto the movie scene in 1998 with her film debut in The Parent Trap, and the world quickly fell in love with the adorable freckle-faced 11-year-old. But by 2007 Lindsay was less known for her acting chops then for her reckless behavior.
The actress has a rap sheet almost as long as her list of film credits, including multiple DUI arrests, drug possession charges, assault charges, warrants for failure to appear in court, probation violations, hit-and-run accusations, and her famous theft arrest for stealing a $25,000 necklace from a Venice jewelry store. Just when we thought that Lindsay had finally gotten her act together she sabotaged her own reality show, produced by Oprah Winfrey in 2014, by continually refusing to film and speculations of Lindsay being off the wagon began to fly. It’s safe to say that whenever the name Lohan appears in the headlines drama and orange jumpsuits are not far behind.
14. Charlie Sheen – Like Father Like Son
The bad boy gene must run in the family because just like his father, Martin Sheen, Charlie is no stranger to run-ins with the law. With an affinity for hookers and a laundry list of domestic violence accusations, including the time that he accidentally shot his fiancé Kelly Preston in the arm, Charlie Sheen has earned his well-deserved title of bad boy extraordinaire. After being fired from Two and a Half Men in 2011 for “engaging in dangerously self-destructive behavior,” according to a letter released by the legal counsel for Warner Bros Television, many thought that Sheen would finally hit rock bottom, but that didn’t seem to be the case, as Charlie exclaimed during an interview in response, “I’m tired of pretending I’m not a total bitchin’ rock star from Mars.”
But life on the edge doesn’t come without consequences, and all the years of partying finally caught up to this self-proclaimed bad boy in 2016, when the legendary womanizer was forced to announce that he had in fact contracted HIV after engaging in unprotected sex with prostitutes.
13. R. Kelly – The Remix To Ignition…In The News For Pissin’
R. Kelly, the king of R&B, has been arrested three times during his 27-year career leaving him more famous for the outlandish charges brought against him than for his music. Kelly was a rising star when he was first arrested in 1996 after a fight at a gym in Lafayette, Louisiana led to a one-year sentence of probation for battery charges. His next arrest came just two years later in 1998 when he picked up three misdemeanor charges for disorderly conduct, but Kelly’s most notable and shocking arrest occurred in 2002 when a disturbing video was released that showed him peeing on an underage girl during their sexual encounter. As a result of that video Kelly was charged with 21 counts of child pornography. After numerous delays, the trial finally occurred in 2008, and a jury eventually found Kelly not guilty on all counts. Hopefully Kelly has since learned to control his bladder.
12. Jay Z – Beyoncé’s Husband… And Convicted Felon?
Although Jay Z may not be winning the award for the most arrests on this list (and has definitely won more actual awards than the rest of them too), his felony charges do make him one of our more badass offenders. Rap star Jay Z was arrested in New York City in December of ’99 for allegedly stabbing a record executive at a Manhattan nightclub. Originally charged with felony assault, the performer pleaded guilty in October 2001 to a reduced misdemeanor count and was sentenced to three years probation. Jay Z is no stranger to violence. He told Oprah in an interview that he shot his 16-year-old brother when he was 12, and Jay Z was also shot three times himself while growing up in Brooklyn. Who knew that Blue Ivy’s dad used to be such a badass?
11. Andy Dick – King of Comical Arrests
Andy Dick has been a fixture in the world of comedy for decades, but in recent years Mr. Dick has become better known for his outlandish antics off-screen, which regularly end in a visit to the police station. Here’s a quick overview of some of his more bizarre encounters with the law. In 2004, an intoxicated Andy was arrested for dicking around, literally, when he pulled down his pants exposing his bare butt to the staff of a local McDonald’s, after which he faced public nudity charges. In 2008, Dick was arrested on drug and battery charges after allegedly exposing the breasts of a 17-year-old girl in the parking lot of a Buffalo Wild Wings. In 2010, Andy was reportedly celebrating his newfound sobriety at a bar in West Virginia, when he was arrested for groping a female bartender. He was arrested for public intoxication again in 2011 at a Marie Callender’s restaurant, of all places. Lastly in 2014, Dick was cuffed one more time for stealing an expensive necklace right off the neck of a fan. One thing holds true, being a comedian at heart, Dick’s arrest record is good for more than a few laughs!
10. Amanda Bynes – From Child Star To Criminally Insane
As we all know child star Amanda Bynes seemingly went off the deep end, and found herself in heaps of legal troubles with several involuntary hospital commitments for mental heath evaluations to boot. Her most notable hospital stay was after starting a fire in a stranger’s driveway while wearing a blond wig and stripping off her pants. Despite her strange activity, it seems as though most of Amanda’s legal troubles could have been avoided if she would have just stayed out the car because the majority of her arrest stem from traffic related violations, when she can easily afford to hire a driver! In 2012 Bynes was arrested for a DUI after trying to pass a police car in her BMW and sideswiping the police vehicle. Shortly after her DUI, Bynes was pulled over on two separate occasions for driving on a suspended license, and was also accused of a hit-and-run. Then in 2014, Bynes allegedly stopped her car in the middle of a Los Angeles intersection, and the California Highway Patrol booked her for her second DUI in regards to the incident. How about you us all and yourself a favor and stay off the road Amanda!
9. Heidi Fleiss – Hollywood’s Famous Lady Of The Night
Heidi Fleiss, known as the Hollywood Madam, ran a high-class prostitution business servicing some of the industries’ top A-list celebrities, until her infamous arrest in 1993. Charged with multiple counts of prostitution and tax evasion, Fleiss spent 3 years in prison following her arrest. Upon her release, she became a notorious television personality appearing in several late-night talk shows, documentaries, and reality TV series, including Celebrity Big Brother and Celebrity Rehab with Dr. Drew. In 2013, Heidi made the news once again, when police found over 300 marijuana plants growing at her Pahrump, Nevada home that she shares with her numerous pet parrots. Fleiss was not arrested following the discovery of the plants, and this bizarre character that was once the famous Hollywood Madam will remain free to tend to her flock of squawking birds that she admittedly sometimes shares her bed with.
8. Paris Hilton – Heiress Of Handcuffs
Heiress and notorious wild child socialite Paris Hilton has been arrested a grand total of three times. Her first arrest in 2006 for a DUI and subsequent probation violations left her saying “that’s hot” to handcuffs. Despite her family’s fortune, she was forced to spend 45 days in jail for the offense. If you thought that time in the slammer would teach this wealthy princess a lesson, then think again because party girl Paris continued on her clubbing spree racking up her most serious offense in 2010, when she was arrested inside the Wynn hotel in Las Vegas after a small bag of cocaine fell out of her purse in front of a police lieutenant. The heiress sidestepped felony drug charges, which could have carried up to a year in jail, by copping to a pair of misdemeanors. This is unfortunate because if anyone could truly make orange the new black, Paris could.
7. O.J. Simpson – There Really Is No Stopping “The Juice”
You would have to be living under a rock to not be familiar with famous O.J. Simpson case after all of the media coverage, crime documentaries, and TV shows that have been airing on the subject lately. O.J. also known as “The Juice” is better known for his run-ins with the law than his career as running back, after his 1994 arrest for the murders of his ex-wife Nicole Brown Simpson and Ron Goldman, which he was eventually found not guilty for during the racially charged trial of the century. The O.J. Simpson trial was easily one of the most watched and highly publicized murder trials in history, but the saga didn’t stop there because in 2007 the infamous O.J. made headlines again when he was arrested for armed robbery and kidnapping at a hotel in Las Vegas. He is now serving his 33 year sentence for the 2007 crimes he committed in the Lovelock Correctional Center in Nevada.
6. Bobby Brown – Enough Said
Bobby Brown, a Grammy Award-winner and member of the legendary music group New Edition, used his bad boy skills to land the late-great Whitney Houston, but their 14-year-long marriage eventually caused both of their lives and careers to come crashing down. On top of the admitted excessive drug use and infidelity, Bobby Brown was arrested for battery in 2003 for allegedly hitting his wife, Whitney. Prior to that incident he had several run-ins with the cops. His rap sheet includes arrests for a DUI, driving without a license, resisting arrest charges, and drug possession charges. The tumultuous romance of Whitney Houston and Bobby Brown just goes to show you that some rebels can’t be tamed.
5. Nicole Richie – From Heroin Chic To Happy Homemaker
Nicole Richie was part of the infamous Hollywood party crowd experimenting with drugs and getting into trouble during her early years. She was busted for heroin possession and driving with a suspended license in 2003, when police found drugs in her Mercedes-Benz. After a couple of stints in rehab, Richie was arrested again in 2006 for her second DUI charge, after driving her car the wrong way down a Burbank freeway. Nicole may have had a troubled past but unlike many of the young Hollywood starlets that ran in her inner circle, Nicole was able to navigate her way though her problematic past and solidify a positive reputation for herself as a successful fashion designer, wife, and mother of two. She even founded a children’s charity in 2007, The Richie-Madden Children’s Foundation.
4. Randy Quaid – That Other Quaid Brother
The eccentric actor Randy Quaid, best known for films such as Christmas Vacation and Independence Day, has been on the run from the law since 2009, in a bizarre string of court cases and claims that Hollywood killers are out to get him. So what exactly happened to this other, more disheveled Quaid brother? Well it all began when Randy Quaid and his wife were arrested for skipping out on a $10,000 dollar bill at a hotel in Santa Barbara in 2009. Then in 2010, the Quaid’s were strangely arrested again on burglary and vandalism charges, when they illegally occupied a guesthouse they formerly owned without the permission of the new owner, and caused nearly $5,000 worth of damages to the property. The Quaid’s then fled to Canada after missing their California court appearance over the felony vandalism accusations, where they were eventually arrested in Vancouver on immigration violation charges, and were finally taken back into U.S. custody almost five years after this saga began. So what was their reasoning behind all of this you may ask? The Quaids announced to the media that this was all a conspiracy from a shady Hollywood group of conspirators called the “Star Wackers” who were out to get them. That seems plausible…
3. Shia LaBeouf – Actor, Inmate, And Author Of “Prison Ramen”
Shia LaBeouf has a very long and colorful rap sheet, with multiple arrests starting as early as age 9. This Transformers star has been incarcerated five times and counting, and is often noted for his bizarre antics involving the law. One of his more notorious arrests was for the time that he was charged with two counts of disorderly conduct, one count of criminal trespassing, and one count of harassment after disrupting a performance of Cabaret, starring Alan Cumming and Michelle Williams, at Studio 54. LaBeouf has had such a long and dramatic history of incarcerations that he is actually getting candid about his time spent in jail in his new book titled Prison Ramen, which also includes some yummy recipes from behind bars.
2. Michelle Rodriguez – Fast and the Furious Jail Time
Fast and Furious not only describes tough actress Michelle Rodriguez arrest history of DUI’s, but also her time spent in jail. The Avatar star has had several run-ins with the law, mostly related to charges of drunk driving. In 2003 Rodriguez plead no contest to drunk driving, hit-and-run charges, and driving on a suspended license charges. In 2006, Michelle served just four hours and 20 minutes of a 60-day jail sentence for violating her probation requirements for a DUI she received while filming the ABC series Lost in Hawaii back in 2005. In January 2008, the actress was released from jail just 18 days into a 180-day sentence for violating her probation in a second DUI case thanks to overcrowding. It appears as though her preparation for her role in the famous Fast and the Furious film series also applied to the short lived amount of time she spent behind bars.
1. Vanilla Ice – Jail Jail Baby
Robert Matthew Van Winkle, best known for his 90s hit “Ice Ice Baby,” surprisingly has one of longest rap sheets on our list with half a dozen arrests. Ice’s first arrest came in 1998 when the white boy rapper was caught drag racing in his hometown of Dallas. Three years later, he was handcuffed once again after threatening a homeless man with a gun. After that, Ice managed to stay off the radar for nearly a decade until he landed himself back in jail for assaulting his wife while driving, which resulted in court-ordered therapy. Seven years later, Ice was charged a second time for assault on his wife but the charges were later dropped after witnesses confirmed it was only a verbal disagreement. His most recent arrest occurred in February 2015 when he robbed a Florida home. These charges were also dropped after Ice completed 100 hours of community service and paid for the stolen items.