One of the earliest lessons we are taught as we begin to enter the world of love and dating is to stay away from the bad boys/girls. And that’s also the first lesson that many of us break as we just can’t fight the lurid appeal of a sexy rule breaker. For what it’s worth, celebrities seem to have just as much trouble staying away from the bad boys/girls as us civilians do. It seems that even those who have their pick of a million nice people– and seem to be nice and sweet themselves– will often still gravitate toward the naughty few.

That is what this list focuses on: 14 women– and one man– who, in one fashion or another, can be classified as celebrity “sweethearts” who married someone who was or is a criminal of some sort. Some of them just have long-ago criminal pasts and one-time offenses, while others continued their illicit ways for years– and in a few cases, even got worse as time went on. The crimes represented on this list run the gamut from misdemeanor assault and drug offenses, to rape– of both adults and minors– and even second-degree murder.

It should be noted that not every person on this list was convicted of a crime, but all have either been formerly charged with one or have had pretty blatant ties to criminal activity.

Here are 15 Hollywood Sweethearts Who Married Criminals.

15. Robin Wright married Sean Penn

Robin Wright and Sean Penn 15 Hollywood Sweethearts Who Married Criminals

Robin Wright’s status as a Hollywood sweetheart was cemented when she portrayed one of the biggest fictional sweethearts in movie history: Princess Buttercup in the fantasy classic The Princess Bride. Going on to play the lifelong love interest of Forrest Gump didn’t hurt, either. And so it goes that Wright eventually fell for a bad boy, in this case the notoriously intense Sean Penn.

While the marriage was the second for both actors, in Penn’s case, his ex was none other than Madonna herself– and it was during his infamously volatile marriage to the Material Girl that he got himself into legal trouble. Penn had zero tolerance for all of the press that came with being married to one of the world’s biggest stars at the time, and he would frequently have violent clashes with photographers. After one such encounter, Penn was charged with assault and sentenced to two months in prison.

After spending a few years dating Wright– and giving her two children– Penn briefly left her for another musician, this time folk singer Jewel. But that ended up being short-lived, and Robin Wright became Robin Wright-Penn in 1996. The couple was married until 2010.

14. Sandra Bullock Married Jesse James

Sandra Bullock and Jesse James 15 Hollywood Sweethearts Who Married Criminals

It’s not only one of the unlikeliest pairings on this list, it was one of the most seemingly mismatched marriages in Hollywood history. You have Sandra Bullock, alongtime rom-com queen who is best known for playing funny, sweet characters; and you have Jesse James, tattooed motorcycle customizer and former heavy metal bodyguard. But it’s not for anyone else but the people in a relationship to decide if two people are right for each other or not, and Bullock and James fell in love and tied the knot in 2005.

It’s true that not all buff dudes with tattoos who ride choppers are criminals, but James has had several legal entanglements. Most notably, he was fined nearly $300K by the state of California for customizing motorcycles that had over ten times the legal limit for carbon emissions. James was also taken to court for a half a million dollars in work that he was allegedly paid for but didn’t complete.

Of course, the most notorious “crime” that James has been known to commit is to cheat on wife Sandra Bullock, an offense that cost him his five-year marriage to the beloved actress.

13. Robin Givens married Mike Tyson

Robin Givens and Mike Tyson 15 Hollywood Sweethearts Who Married Criminals

In the mid-80s, a young actress named Robin Givens was making a name for herself in roles on beloved sitcoms like The Cosby Show and Diff’rent Strokes before finally landing a steady gig on hit series Head of the Class. At the same time, a ferocious boxer named Mike Tyson had exploded onto the scene and quickly became one of the most fearsome fighters to ever step into the ring. In 1988, the two rising stars got married– and things didn’t go very well.

Givens described her marriage to Tyson as “torture, pure hell, worse than anything [she] could possibly imagine.” And he was sitting right next to her at the time, in a joint interview with Barbara Walters. The actress claimed that Tyson was physically and mentally abusive, as well as extremely unstable. Tyson would later infamously describe a particular physical encounter with Givens, calling it “the best punch [he’d] ever thrown in [his] entire life.”

But Tyson didn’t face any legal ramifications for anything he did to Givens. The now-retired boxer and sometimes actor wouldn’t formally become a criminal until 1992 when he was sentenced to six years in prison for the rape of teenage beauty pageant contestant Desiree Washington.

12. Angelina Jolie and Jennifer Aniston Married Brad Pitt

Angelina Jolie Jennifer Aniston Brad Pitt 15 Hollywood Sweethearts Who Married Criminals

Brad Pitt has a distinction that not a lot of people can claim: he’s been married to two women who can be classified as “Hollywood sweethearts,” Angelina Jolie and Jennifer Aniston. He also had a high-profile courtship with a third sweetheart, Gwyneth Paltrow. Other than the child abuse investigation that occurred during the early stages of his separation from Jolie (from which he was ultimately cleared of any legal wrongdoing), Pitt does have a criminal arrest in his past.

In 1988, just as Pitt’s star was beginning to rise, the actor was charged with indecent exposure. However, it’s not quite what you think– Pitt was mooning drivers along California’s Pacific Coast Highway when he was busted by police. Fortunately for Pitt, he had good legal representation on his side, and the indecent exposure charge was eventually reduced to a misdemeanor charge of disturbing the peace.

It seems like something to laugh about now, 25-year-old Brad Pitt showing his prized derriere to the public and getting charged with disturbing the peace for doing so– but had the indecent exposure charge stuck, he would’ve had to register as a sex offender.

11. Jada Pinkett Married Will Smith

Will Smith and Jada Pinkett Smith 15 Hollywood Sweethearts Who Married Criminals

Back when he was best-known by the stage name “The Fresh Prince,” Will Smith was a rapper who set himself apart with his clean-cut image and family-friendly lyrics. Among the worst offenses committed by the Fresh Prince in his songs were staying out too late and getting pulled over for driving without a license. As it turns out, the real Will Smith was involved in a run-in that was more like something a much harder rapper would talk about.

In 1989, fresh off a Grammy win, Smith allegedly ordered his bodyguard to attack record promoter William Hendricks. The resulting attack caused Hendricks to need six stitches, and it almost cost him his vision in his left eye. Smith was arrested, booked, and had to spend a night in jail– although it wasn’t that rough, as he spent his brief jail stay signing autographs.

Although the charges were later dismissed, they were pretty heavy– criminal conspiracy, aggravated assault, and recklessly endangering another person. None of it deterred actress Jada SP from marrying Smith eight years later– though having been close friends with Tupac Shakur, Pinkett was no stranger to spending time with rough-and-tumble hip-hop artists.

10. Beyoncé married Jay-Z

Beyonce and Jay Z 15 Hollywood Sweethearts Who Married Criminals

While there is some dispute as to the “level” of Jay-Z’s pre-fame teenage drug dealing– some people have claimed he was moving five figures worth of cocaine every week at his peak– the artist formerly known as Sean Carter has, at the very least, confirmed that he spent part of his youth as a cocaine dealer and it was only by luck that he was able to escape the hard jail time he deserved.

However, by most accounts, he had left his life of crime behind once he became a platinum-selling rapper and the eventual husband of pop queen and Destiny’s Child frontwoman Beyoncé Knowles. That is, except for one high-profile 1999 incident at a club where Jay was accused of stabbing a record executive.

Jay-Z surrendered to police the day after the incident and cooperated fully, pleading not guilty to the incident but still taking a plea deal that reduced the charge to a misdemeanor which only carried a sentence of three years probation.

9. Sharon Tate married Roman Polanski

Sharon Tate and Roman Polanski 15 Hollywood Sweethearts Who Married Criminals

Sadly, the name Sharon Tate is more associated with her killed by Charles Manson’s followers than her acting career. Before being brutally stabbed 16 times– while 38 weeks pregnant– Tate was a promising young actress who earned raves for her role in the cult classic Valley of the Dolls. She was also married to actor and director Roman Polanski, the father of her unborn child.

Eight years after Tate’s murder, Polanski was arrested for sexual conduct with a 13-year old girl with charges that included drugging and raping her. Though he maintained his innocence, he accepted a plea deal that required him to at least plead guilty to having sex with a minor.

After the judge changed his mind and decided to pursue the original charges in full, which would’ve meant 50 years in prison, Polanski fled the country and has never returned– though, astonishingly, Hollywood continues to allow him to make movies and be nominated for Oscars.

8. Sarah Jessica Parker married Matthew Broderick

Sarah Jessica Parker and Matthew Broderick 15 Hollywood Sweethearts Who Married Criminals

This is definitely a marriage where both parties can be classified as Hollywood sweethearts– and perhaps Broderick is actually the bigger sweetheart of the two, having played the iconic role of lovable troublemaker Ferris Bueller and providing the adult voice of Simba in The Lion King. But Parker is definitely a sweetheart in her own right… and she did marry a criminal.

While vacationing with then-girlfriend and Ferris Bueller co-star Jennifer Grey in Ireland, the car that Broderick was driving veered over into the oncoming traffic lane and was involved in a head-on collision with another vehicle. Grey’s injuries were relatively minor, and Broderick ended up with a collapsed lung, fractured ribs and leg, and a concussion. But the two people in the other car, a mother and her adult daughter, were killed instantly.

Broderick claimed that he had no recollection of the accident or anything else that happened that day, and couldn’t explain why he lost control of his vehicle. There were also no drugs or alcohol in his system. He was initially charged with causing death via dangerous driving, but the charges were reduced to just reckless driving and he only had to pay a $175 fine.

7. Eric Dane married Rebecca Gayheart

Eric Dane and Rebecca Gayheart 15 Hollywood Sweethearts Who Married Criminals

We finally get to a male sweetheart who tied the knot with a female criminal. Eric Dane gained major popularity– and elicited major lust– when he played the role of Dr. Mark “McSteamy” Sloan on the medical drama Grey’s Anatomy. In 2004, McSteamy settled down with actress and former “Noxzema Girl” Rebecca Gayheart, with her biggest non-commercial roles occurring in the films Jawbreaker and Urban Legend.

The courtship between Dane and Gayheart began at the tail end of her probation that came from a 2001 vehicular manslaughter charge. The actress hit a 9-year-old boy with her car as he crossed the street, and he succumbed to his injuries the following day. Gayheart pleaded no contest to the charges, and was sentenced to three years of probation and 750 hours of community service, and had to pay a fine of $2,800.

Dane obviously didn’t dwell on Gayheart’s criminal past, and married the actresses after only 10 months of dating, eventually having two children with her.

6. Whitney Houston married Bobby Brown

Whitney Houston and Bobby Brown 15 Hollywood Sweethearts Who Married Criminals

The music world can be very incestuous, with musicians often staying within their industry in the pursuit of sex and love. It’s also not uncommon for those inter-musician pairings to involve couples that are a bit mismatched, typically involving a sweet girl getting lured in by a bad boy. Still, the entire world was shocked when seemingly innocent pop icon Whitney Houston got involved with– and eventually married– R&B rebel Bobby Brown.

Unfortunately, Houston and Brown’s marriage seemed to bring out the worst in both of them. Houston suddenly started showing signs of drug use, a stark contrast from her squeaky-clean image up to that point; and Brown, who had previously just been a drinker and marijuana user, escalated his drug use to cocaine after marrying Houston. In the mid-2000s, things got even worse as Brown was arrested several times for charges ranging from missing child support payments, to drunk driving, to physically abusing Houston.

To hear both Brown and Houston herself tell it, she already was that “bad girl” before marrying Brown, and finally just decided to show that side publicly. Either way, it was a marriage that ultimately didn’t seem to do either one of them any good.

5. Elizabeth Hurley married Hugh Grant

Elizabeth Hurley and Hugh Grant 15 Hollywood Sweethearts Who Married Criminals

Everyone has made poor judgment calls in their lives. Fortunately, most of us don’t have to deal with our bad decisions being turned into a media circus where we are forced to answer for them on late-night talk shows. That is exactly what happened to actor Hugh Grant when he made the terrible judgement call of not only soliciting a prostitute off the street, but having the “business” be conducted in a publicly-parked car.

His now famous response to Jay Leno asking him just two weeks later, “What the hell were you thinking?” was to simply say, in his charmingly English way: “I did a bad thing. And there you have it.”

Of course, what makes Grant’s mistake all the worse is that he just so happened to be married to actress Elizabeth Hurley at the time, one of the most beautiful women in the world who was just on the cusp of her big breakout role in Austin Powers: International Man of Mystery. Thus began Hurley’s transition from just that voluptuous beauty on Hugh Grant’s arm to being a legitimate star in her own right.

4. Veronica Bennet (aka Ronnie Spector) married Phil Spector

Phil Spector and Ronnie Spector 15 Hollywood Sweethearts Who Married Criminals

The music industry has a lot of figures that have very complicated legacies, people who have contributed great art to the world but also have some very troubling skeletons in their closets. Phil Spector is such a figure, a man who is rightfully considered one of the most influential people in the history of pop music– but one whose dark side includes involuntarily imprisonment, psychological abuse, and second-degree murder.

Veronica Bennet, better known by the stage named Ronnie Spector following her marriage to the producer, was one of the most famous voices of ’60s pop music. As the lead singer of The Ronettes, she was the singer of such megahits as “Be My Baby” and “Baby, I Love You.”

However, the marriage between the Spectors was far from idyllic. Ronnie said she suffered years of psychological torment at the hands of Phil. She was kept in their mansion against her will and finally had to literally escape barefoot.

That wasn’t even the worst offense the increasingly reclusive producer would commit, as he would later be convicted of murdering actress Lana Clarkson, a crime for which he is currently serving a life sentence.

3. Denise Richards married Charlie Sheen

Denise Richards and Charlie Sheen 15 Hollywood Sweethearts Who Married Criminals

Charlie Sheen didn’t waste too much time settling into the role of bad boy both on-screen and off, already in the position to parody his reputation via his police station cameo in Ferris Bueller’s Day Off in 1986. The actor was also a notorious ladies’ man, and seemed like he was enjoying the freedom to bed young actresses, models, and adult stars way too much to ever actually settle down.

Finally, in 2002, it seemed as though a woman was finally going to tame the notorious Hollywood wildman who, only a few years prior, was hospitalized due to a cocaine overdose. Denise Richards, who had appeared in cult classic films Wild Things and Starship Troopers and was the Bond Girl in The World is Not Enough, had managed to get Sheen to put a ring on it. They even had a traditional Roman Catholic wedding.

Among the reasons that Richards would later end their marriage after less than four years were Sheen’s erratic behavior that included drug use and death threats. Sheen would later be arrested for assaulting his next (ex)wife, Brooke Mueller, as well as additional drug-related charges.

2. Marilyn Monroe married Joe DiMaggio

Marilyn Monroe and Joe DiMaggio 15 Hollywood Sweethearts Who Married Criminals

Marilyn Monroe was one of the original Hollywood sweethearts, capturing the fascination of an entire nation with her natural charm and unfathomable beauty. It was the whole “men want her, women want to be her” thing.

Who better to marry Hollywood’s most beloved woman than professional sports’ most beloved man? And so, for a year in the mid-50s, the impossibly perfect couple of Marilyn Monroe and baseball star Joe DiMaggio existed to enrapture their collective fanbases– which was basically every living person at the time.

To say that Monroe’s life was as troubled as her choice in men would be an understatement. In addition to an affair with John F. Kennedy that was all but officially confirmed, Monroe’s marriage to DiMaggio was that of a Hollywood sweetheart marrying a man with some pretty obvious mafia ties. Not that Monroe needed the extra clout, but in the mid-20th century, there were few greater positions of power than to be in the good graces of the mob.

1. Aaliyah married R. Kelly

Aaliyah and R Kelly 15 Hollywood Sweethearts Who Married Criminals

In the case of R. Kelly marrying young pop star Aaliyah, it was a man essentially becoming a criminal by marrying a celebrity sweetheart. With Aaliyah only being 15 at the time, the pair’s marriage was eventually deemed unlawful and later annulled. But having Aaliyah’s debut album– produced by Kelly and having him lurking in the background of the album cover– titled Age Ain’t Nothing but a Number seemed to suggest a man who was almost flaunting their inappropriate relationship.

Kelly’s preference for teenage girls didn’t end with Aaliyah, as stories have circulated for years that the “I Believe I Can Fly” singer is frequently on the lookout for his next underage ingenue. In 2002, Kelly was indicted on 21 counts of child abuse after photos were allegedly found in his possession of an underage girl, as well as a video that reportedly shows him urinating on her.

The 50-year-old musician is currently at the center of another scandal after three different sets of parents came forward and accused him of keeping their daughters– one who is only 18– prisoner in a manipulative “cult”, though there has yet to be sufficient evidence for an official investigation into the matter.

Can you think of other sweethearts in Hollywood who married criminals? Let us know in the comments!

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