The 15 Most Criminally-Challenged Celebrities

Some celebrities just can't stay out of legal trouble.  It doesn't matter how many times they get pulled over, arrested, and handcuffed - they just keep repeating the same mistakes. Part of it may be due to addiction, psychological problems or pure stupidity. And part of it may be outright arrogance.

Fortunately, the world of law enforcement can be quite forgiving if you’re a celebrity.  You tend to get more than one chance at redemption - try a dozen. And Hollywood just seems to love a train wreck. The more our favourite celebs screw up, the more it seems we want you around.  Just in case you screw up yet again.

And as much as Hollywood loves a fall from grace, it loves a comeback even more.  Face it - who doesn't love a happy ending?

The following fifteen are the most criminally-challenged famous faces. Some of them eventually got their act together and revitalized their career. Others haven’t quite bottomed out yet, and may yet show up again on the police blotter.


15 Sean Penn

The bad boy of the 1980s has mellowed to the point of boring respectability. Still, his track record does give you pause. Penn’s problems began with his marriage to Madonna in 1985. Hounded by the paparazzi, Penn got into numerous fights.

He once beat a film extra, earning himself a month in jail. In another incident, he was charged with attempted murder in Macau after holding a photographer off a ninth story balcony. Legend has it he escaped and fled to Hong Kong. He was eventually pardoned.

As recently as 2009, Sean Penn received  probation after a caught-on-tape kicking incident with a photographer. Still, his notorious run-in with Madonna, who charged him with felony assault in a marriage-ending incident, is the incident that sticks in most people's minds. Madonna chose not to pursue prosecution.

14 Snoop Dogg


The notorious hip hop artist has reinvented himself drastically in recent years. Gone is the marijuana-smoking gangster rapper. These days, Snoop is more of an amusing, responsible reality TV show dad. He seems like such a likable, easy-going guy that it’s hard to imagine he once hung out with the notorious Crips gang.

Snoop's early life as a rapper was peppered with arrests for marijuana and gun possession. He spent a night in British jail for vandalizing a duty free shop at Heathrow Airport. For that, he got banned from that country for several years. He was also banned from Norway for two years for marijuana possession. More serious stuff has included a murder charge (he was acquitted), assaults, and an early cocaine possession charge.

Somehow, none of these multiple charges have led to serious time in prison. And besides the infrequent pot possession charges, he seems pretty clean these days.

13 Lindsay Lohan


Where do you start with this actress? At some point early on in her life, Lohan's career took a back seat to her self-inflicted legal problems. It can probably be traced back to 2007, when she received her first DUI and cocaine possession charge. A second soon followed. Then there were the repeat trips to rehab, the multiple car accidents, and the theft of $2500 in jewelry.

A lot of LiLo's problems are of the self-inflicted, scratch-your-head variety. Twice she has been to jail because of her failure to follow court orders. And just last month, she had her required community service extended three more months yet again, because of her failure to complete her work.

12 Charlie Sheen


There are no half-measures with the former 'winning' star of Two And A Half Men. When he gets involved with the legal system, odd things happen. People get shot. Hookers get locked in closets. And cars disappear off cliffs.

Charlie Sheen's more self-destructive moments have involved a combination of drugs and women. He’s been charged with drug possession after overdosing, resulting in probation (later extended after a repeat incident). He was charged with assaulting his wife Brooke Mueller in 2009 (pleading guilty to a reduced charge). The 2010 hooker-in-the-closet incident was pure Sheen, with the star being forcibly removed from his hotel suite after causing $7000 in damages to the room in a drug-fueled rage.

Still, the Sheen incident that stands out the most goes all the way back to 1990. This was when Sheen’s girlfriend Kelly Preston got shot in the arm. Sheen has claimed it was Preston who accidentally shot herself after a gun fell out of a pair of Sheen’s pants.

11 Jenelle Evans


Does being a Teen Mom drive its participants to commit crimes? Or are the participants chosen for their criminal leanings? It’s an interesting question. After all, 16 and Pregnant/Teen Mom 2 star Jenelle Evans has been arrested no less than 11 times since 2010 – the year she first appeared on the reality show.

She’s been quite a busy gal, raising a kid (although her mom does that mostly) while spending so much time at court. She’s had a few short stints in jail, but most of the convictions led to probation. The charges included drug-related incidents, a missed court date, a break and enter charge, an assault caught on film (there's always a film crew handy), and a couple of disturbing the peace incidents. Just this week she showed up again in court, after allegedly driving with a suspended license.

10 Natasha Lyonne

via CBS

This one has a happy ending. The actress (American Pie, Orange Is The New Black) had a party girl reputation early in her career, not to mention a bad rep with landlords. She pled guilty to a DUI in 2002, and paid a fine. After getting kicked out of one apartment after multiple complaints from neighbours, she was charged with criminal mischief, harassment and trespassing by another neighbor. Then an arrest warrant was issued when she didn't show up to face the charges.

But it all ended happily. The charges were eventually dropped, Lyonne went to rehab, and her career picked up. She recently received an Emmy nomination for her role as Nicky on Orange Is The New Black.

9 Justin Bieber

Over the last couple of years, the teen idol has had numerous run-ins with the law. Bieber had to pay $81,000 in restitution after egging his neighbours house, and was again charged with vandalism in an incident in Brazil.

Then there were the vehicular problems – a DUI and reckless driving charge (which ended up resulting only in a fine), a collision leading to an assault charge, and another assault charge involving a limo driver. Apparently, Bieber gets angry and brave while surrounded by his bodyguards and entourage.

There have  been other moments (invariably involving paparazzi) that didn’t lead to official charges, but added to his new image as a bad boy. Actually, ‘bad’ might be overselling it. The Ottawa Sun labeled him 2014’s most annoying celebrity. A recent apology seemed sincere but the jury is still out on the Biebs.


8 Martin Sheen


Does it count if you keep getting arrested on purpose? Unlike his son Charlie, Martin has made a habit of getting himself arrested while protesting things like nuclear weapons, military actions, and the environment. But that’s sort of the point – it’s not a good protest rally unless you get hauled away in handcuffs.

One of his more recent arrests was in 2007, when he was hauled away by police after trespassing at a Nevada nuclear test facility.

In all, Martin Sheen has been placed in cuffs a total of 66 times since 1986 – when he was first arrested for civil disobedience at a protest of President Reagan’s Star Wars initiative.

7 Michelle Rodriguez


It’s not particularly surprising that a star of The Fast and The Furious franchise would have problems with the law when it comes to driving. But Rodriguez sure overdid it.

During a stint filming her role on TV’s Lost in Hawaii in 2005, she was pulled over no less than three times for speeding, and once for DUI. Her conviction on the DUI followed a similar conviction in 2003, and thus violated her probation.

She spent a short time in jail for all that, and would later spend a few more weeks in jail after violating her probation again when it came to performing community service. Since then, though, things have been quiet for Michelle. Maybe she just decided to take a cab.

6 Alec Baldwin

Baldwin comes from the Sean Penn school of dealing with paparazzi. When they make him mad, he’s not afraid to attack. He allegedly assaulted a photographer as far back as 1995 – when one got between him and his wife and newborn child. More recently, an exchange of insults with a photographer lost him his talk show job at MSNBC.

Still, Baldwin’s anger doesn't usually result in charges – just bad press. He certainly didn't win any friends by calling his daughter ‘a pig’ in a leaked phone message. And a lot of fellow passengers were miffed when Baldwin refused to shut off his Words With Friends game before a flight in 2011. He was forced to leave the plane.

But the 30 Rock star graduated to full on charges last May in New York when he was charged with going the wrong way on his bike, and disorderly conduct. Baldwin later tweeted that the cops should be concentrating more on the paparazzi who had staked out his place. He called New York a “mismanaged carnival of stupidity”.

5 Amanda Bynes

This young actress has been in and out of psychiatric care facilities several times in the last few years. That might go a long way to explaining her behavior – which has included multiple DUI charges and hit-and-runs in 2012.  In 2013, she was alleged to have tossed a bong out her apartment window, resulting in charges of possession of marijuana and tampering.

That same year, she also set a small fire in a stranger’s driveway. With her parents now her guardians, Bynes has attempted to get her act together with varying degrees of success. On Twitter, she accused her father of molesting her and placing a microchip in her brain. And in September, she was charged yet again with a DUI, though those charges were recently dropped.

4 Robert Downey Jr.

The acclaimed actor decided a long time ago to stop with the drugs and booze and get his act together. Still, he didn't have much of a choice. His criminal activity had gotten way out of hand. Downey spent the years of 1996 to 2001 in an out of court and jail. Drugs were the culprit. He kept getting caught with them – plus the odd handgun.

Yet even after falling asleep in a neighbor’s house while on a binge, Downey got off with probation. However, he failed his probationary drug test (twice!), and eventually spent a full year in jail. Relapses followed until, faced with a possible four years in jail, Downey cleaned himself up. For good – or at least so far.

3 Amber Portwood

Portwood is another troubled Teen Mom. It’s always a good idea not to commit crimes in front of TV reality cameras. But the Teen Mom star did just that when she assaulted her boyfriend Gary repeatedly on the MTV show. After public outrage, charges were laid (for both assault and drug possession) and she received conditional probation.

Unfortunately, Amber didn't seem to want to play by the rules set down by the court. She failed to live up to the conditions of her probation several times and  refused and failed drug tests.

She was eventually convicted of five years in prison, but spent only one behind bars. During her stint in jail, she told Dr. Phil that she was high for most of her appearances on Teen Mom.

2 Andy Dick

Comedian Dick has a long history of problems with alcohol. He even did a stint on the TV reality show Sober House with Dr. Drew.  Though he’s been to rehab, the problems persist and likely contributed to his many, many run ins with the law. In 1999, he ran his car into a pole and ended up with a hit and run charge, a DUI, and charges for drug possession. None of those charges resulted in more than probation for the NewsRadio star.

Since then, he’s repeatedly been cited for indecent exposure. He pulled down a teenager's top, and groped a bartender and patron, leading to multiple charges but no jail time.

Though no charges were laid, he’s also been ‘escorted’ out of  public events, stand-up gigs and even The Jimmy Kimmel Show. And just last November, he added grand theft to his resume when he snatched a necklace from a guy on Hollywood Boulevard and rode away. Jail time may be next for Dick.

1 Flavor Flav

The cartoonish reality star was pulled over  just this year for speeding.  Police soon discovered  he already had 16 suspensions of his license. Yikes.

Yes, it’s been an interesting life for Flav, who had already been in and out of prison by grade eleven. He’s been charged several times for domestic abuse (one involving a knife), as well as drug-related crimes, and once spent 90 days in jail after shooting at a neighbor - which wasn’t too bad a sentence considering he was charged with attempted murder.

In 2002, he spent an additional nine weeks in jail for parole violations for several drug and physical abuse convictions. As for the most recent vehicular violations, Flav had an excuse. He was racing to his mother’s funeral.


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