The Worst Celebrity Couples We’re Still Trying to Forget

Long before the days of round-the-clock celebrity surveillance, film fans were routinely caught off guard when beloved stars called it quits on their relationships. The one exception, perhaps, was Elizabeth Taylor, a longtime screen veteran who was as well known for her unlimited talent and piercing violet eyes as she was for her tumultuous offscreen romances. Married a total of eight times, it was Liz's partnership with two-time husband Richard Burton that set tongues wagging most frequently. The on-again-off-again dynamic constantly had fans on the edge of their seats, especially considering reports were rife with references to their volatile relationship, public screaming matches, accusations of affairs and alcohol addiction — although the biggest addiction neither overcame was the unhealthy one they had for each other.

Royal romances are often fraught with tension — made worse by the fact that, up until recently (we're looking at you, Harry and Meghan!), they had to meet the queen's rigid guidelines. Such was the case for Charles and Diana. While the heir to the British throne had fallen truly, madly, deeply in love with Camilla Parker Bowles in the 1970s, he was ultimately married off to an 18-year-old Diana Spencer — a woman deemed vastly superior by the Royal Family thanks to her aristocratic upbringing, chaste personality (read: her virginity) and the fact that, unlike Camilla, she hadn't been previously married. For the duration of their tumultuous marriage, Diana battled an eating disorder, bouts with depression, paranoia and Charles' subsequent affair with his former flame. Their inevitable split in 1996 was big news — and the whole tragic situation was capped off by Diana's untimely death the following year.

Try to find one person in your life who thought Tom Cruise and Katie Holmes made a cute couple. (Spoiler alert: You won't.) From Cruise's cringe-worthy couch-jumping antics on The Oprah Winfrey Show to Holmes' revelation that she'd had a crush on Cruise as a little girl (there's a 16-year age gap between them), there was nothing sweet about this odd, kinda icky pairing. Both fans and Hollywood elite, alike, were left scratching their heads, wondering what could have drawn them together (there were whispers that it was pre-arranged, complete with signed contracts). And lets not forget the dark spectre looming in the background since day one: Scientology. In their five years together, Holmes, once a bubbly TV star riding high after a starring role on Dawson's Creek, became quiet and passive alongside her more ebullient spouse. Years after the high-stakes divorce settlement and custody battle over their daughter, Suri, we still don't know the full story of what went on behind closed doors.

According to sources at the time, it was a whirlwind love affair — at least at first. This was before all the tabloid exposes on Scientology and rampant speculations as to Tom Cruise's sexual orientation. In 1990, Cruise and Nicole Kidman met on the set of their hit film Days of Thunder and exchanged vows later that same year. The duo later adopted two kids. Although it's still unclear as to what exactly drove a wedge between the couple after 11 years of marriage — many point to Cruise's undying devotion to the Church of Scientology. The action star abruptly filed for divorce from Kidman in 2001, the same year the Aussie actress found herself Oscar-nominated for her role in Moulin Rouge!, and Cruise received full custody of their kids, Isabella and Connor. The split was so nasty, in fact, that Kidman allegedly hasn't seen her kids since, even though both are now in their 20s.

Whitney Houston could boast a vocal range few other singers could match and she reigned supreme over the pop charts throughout the 1980s and 1990s, culminating in her blockbuster soundtrack for the 1992 flick, The Bodyguard. This ultimately made her downward spiral during her marriage to Bobby Brown all the more tragic. Brown is often maligned for enabling a fragile Houston's severe drug dependency, which he has since admitted was at its lowest point toward the end of their marriage. Throughout their 14 years together, the couple were consumed by infidelity and drug use. Since her death in 2012 from coronary artery disease and cocaine intoxication, her daughter with Brown, Bobbi Kristina, suffered an eerily similar fate in 2015, dying at the age of 22.

Frankly, it's been a little exhausting keeping tabs on these two. Although it hadn't exactly been smooth sailing to the alter for pop superstar Miley Cyrus and Aussie actor Liam Hemsworth, many devoted fans thought they were finally in it for the long haul after exchanging vows in December 2018. But less than a year later, and the pair announced they'd split — again. Adding to the drama were photos of Cyrus kissing Brody Jenner's ex-wife, Kaitlynn Carter, during a recent trip to Lake Como, leading to speculation that the pop star up and left her hubby over an affair. That being said, we have a feeling this won't be the last we hear of the on-again/off-again pair.

If there's one thing Pamela Anderson and Tommy Lee gave us (aside from a certain home video that ushered in the era of celebrity sex tapes — so, thanks?), it's the can't-look-away drama of their chaotic marriage. From screaming matches, accusations of abuse and rampant drug use (at least on his end), once all was said and done it was hard to believe the fractious pair were only married for three short years. Although Anderson and Lee have since revealed they're on relatively good terms now — perhaps for the benefit of their two sons — we shouldn't forget that Lee was once sentenced to six months in jail for battery. Anderson filed for divorce in 1998.

The very definition of a bad romance, the destructive, enabling nature of Kurt Cobain and Courtney Love's courtship mostly played out in the tabloids, but even the major publications couldn't resist writing about the toxic, drug-fueled exploits of rock 'n' roll's royal pair. The relationship was intense, albeit fleeting, with a quickie wedding in 1992 after only four months of dating (by then, Love was already pregnant with their daughter, Frances Bean). What followed was a rapid descent into hard drugs and emotional manipulation on both sides that tragically culminated in Cobain's suicide in 1994.

As it turned out, it was far from a match made in pop music heaven. Although fans of artists Rihanna and Chris Brown were initially thrilled when the two paired off in 2008, it all fell apart a year later after a highly-publicized domestic violence charge. On the morning of the 2009 Grammy Awards it was announced that the superstars would no longer be attending. At the time, it was implied that there'd been a minor car accident and the two were on the mend. So the truth bomb that followed shook their fanbases to the core. Brown had actually been arrested for assaulting Rihanna and leaving her with black eyes and a split lip. He was charged with felony battery and forced to serve five years of counselling and community service. His half-assed PR-stunt apology and defensive Twitter rants lost him a slew of fans. As for Ri-Ri, she's moved on to bigger and better things.

It's hard to separate Charlie Sheen the actor from Charlie Sheen and his 2011 meltdown when he was living with a slew of porn stars he referred to as his "goddesses" and got himself fired from his top-rated sitcom Two-and-a-Half Men due to substance abuse and unprofessional behaviour on set. So it's easy to forget that he was once paired off with model-actress Denise Richards, with whom he has two daughters. In 2006, after four years of marriage, Richards was granted a divorce settlement after having accused Sheen of rampant alcohol and drug abuse and threats of violence. Even now, the Real Housewives of Beverly Hills star claims Sheen owes her more than half a million dollars in child support. When it comes to relationships, Sheen is never "winning."

Ugh. Remember K-Fed? The reviled, multi-hyphenate (read: talentless) rapper-DJ-actor-model-wrestler who somehow wooed the Queen of 2000s Pop right off her feet? Although they only had less than three years of "wedded bliss", Britney Spears and Keven Federline were everywhere. Pass any magazine rack in a grocery store and you were bound to come across tales of their continuous fights, accusations of infidelity and custody battles over their two sons. Federline has never been able to shake the shadow of being called a "gold digger" who left his previous girlfriend while she was pregnant in order to get with Spears. He caught the fragile pop star at a time when she was still learning to assert her independence in the industry and their falling out undoubtedly played a role her public meltdown in 2008 and the loss of custody of her two kids.

While pop star Justin Bieber seems happy with wife Hailey Baldwin, it wasn't always sunshine and rainbows in the love department for the Canuck crooner. As recently as this year, fans were still being pulled in by the unfolding "Jelena" drama that was Bieber's on-again/off-again relationship with singer Selena Gomez. Still fresh in our collective memories are Bieber's frequent run-ins with the law – from physical altercations at clubs to drunk driving arrests – and Gomez's not-so-secret trips to rehab. In 2016, during another "off-again" period, they engaged in an "Instagram war" after Gomez called Bieber out for posting intimate photos of himself with a new girlfriend. The pair were last seen canoodling in early 2018 – shortly before Bieber met and married Baldwin. We're... cautiously optimistic that it's officially over between these two now.

Ava Gardner was revered for her acting chops and beauty, but it was her tumultuous relationship with Ol' Blue Eyes himself that truly captivated fans. Already twice divorced by the age of 25, Gardner entered an affair with the older, married Frank Sinatra in 1949 — a fact they didn't exactly try to keep under wraps. From late-night phone calls to the Sinatra home and a dual arrest for a "drunken joyride" that culminated into a "shootout" that left storefront windows damaged by their pistols, the pair exchanged vows in 1951 after Sinatra forced a quickie divorce on wife, Nancy. The two would go on to have numerous affairs behind each others' backs and, by all accounts, the marriage was always fraught with tension. The pair split in 1957.

There was a whirlwind week in 2010 that saw Sandra Bullock win a Best Actress Oscar for her role in The Blind Side, while also learning about some shocking allegations against her husband, former Monster Garage host Jesse James. Several women came forward claiming James had affairs with them throughout his marriage to Bullock. The beloved actress quickly filed for divorce, which was granted in 2012. But Bullock and her loyal fans had the last laugh as the star continues to rake in big money at the box office (ever heard of a little movie called Gravity?) and adopted two kids on her own, son Louis and daughter Laila. Jesse who?

Although fans didn't know it at the time, during the height of their musical partnership, Ike Turner was emotionally and physically abusing wife, Tina. The pair skyrocketed to fame in 1971 with their rousing, Grammy-winning cover of Creedence Clearwater Revival’s “Proud Mary." But, instead of celebrating their considerable achievements, it was Ike's violent behaviour and self-sabotaging ways behind the scenes that consumed the couple and pushed Tina to the brink. As Tina later recounted in her 2018 memoir, My Love Story, all sexual encounters with Ike were “an expression of hostility — a kind of rape — especially when it began or ended with a beating.” Even the 1993 film, What's Love Got to Do With It, doesn't cover half of what happened behind closed doors.

It's been five years years since Amber Heard filed for divorce from embattled actor Johnny Depp. The proceedings have largely played out in the court of public opinion so far, with Heard's allegations of abusive behaviour that occurred throughout their 15-month marriage at the forefront of the news coverage. In court documents, Heard wrote: "I endured excessive emotional, verbal and physical abuse from Johnny, which has included angry, hostile, humiliating and threatening assaults to me whenever I questioned his authority or disagreed with him." Depp has denied all charges. It's a shocking fall from grace in recent years for the former in-demand Hollywood heartthrob who is also facing a lawsuit from two former bodyguards over unpaid wages and accusations of unprofessional and intoxicated behaviour on set.

When former child star Lindsay Lohan and British DJ Samantha Ronson first went public with their relationship in 2008, it was big news. Like, big big. We can't downplay how much ink was spilled over the pairing. Alas, it was only a 12-month romance that saw Lohan go from deeply "in love" to describing her relationship as "too toxic to survive." The couple made headlines thanks to their public screaming matches and hard-partying ways, as the relationship quickly spiraled out of control. When asked in 2018 if she considers herself sexually fluid, Lohan brushed off the question with a casual, "No. I like men." When pressed, she laughed it off, saying "I was living in LA", leading some fans and social commentators to question whether Lohan is now "erasing" her queer relationship.

Former Baywatch star Carmen Electra and NBA superstar Dennis Rodman made waves back in 1998 when they exchanged vows in a gaudy Las Vegas ceremony. While the two certainly seemed to be have a great time at red carpet events, their relationship fizzled soon after the nuptials. Within nine days of uttering "til death do us part," Rodman had filed for an annulment, claiming he had been of "unsound mind." Although the pair briefly reconciled, they officially split four months later. Electra has since told US Weekly that her brief marriage to Rodman was "the worst," stating that the relationship was destructive, manipulative and put her in a bad emotional state.

Few major Hollywood stars have fallen from grace — and sanity — faster than Mel Gibson. The once-beloved Oscar-winner and sex symbol has been on a steady decline since his alcohol-fueled profanity-laced and anti-Semetic arrest rant in 2006 and the fallout from his highly-publicized split from Russian pianist, Oksana Grigorieva. Their turbulent, and reportedly physically violent, relationship officially ended almost as abruptly as it began after recordings were released of Gibson unleashing all his pent-up anger and frustration on Grigorieva, who is also the mother of his daughter. Although Gibson has slowly tried to make a "comeback" in recent years (the Oscars gave him a Best Director nod for 2016's Hacksaw Ridge), it's doubtful he'll ever fully be back in our good graces.

Remember this shocking pairing between the King of Pop and the daughter of the King of Rock 'n' Roll? Everything about the relationship of Michael Jackson and Lisa Marie Presley screamed "forced" — from their hasty 1992 wedding (a mere 20 days after Presley's split from first husband, musician Danny Keough) to the supremely awkward on-stage kiss at the 1994 MTV Video Music Awards. During their marriage, Jackson faced child molestation accusations and turned his new wife for emotional support. For her part, Presley became increasingly alarmed over his fluctuating health and addiction to drugs. Although she "wanted to save him," Presley ultimately filed for divorce in 1994, putting an end to one of Hollywood's most unlikely pairings.

Here's one relationship that definitely got off to a questionable start. At only 14 years of age, impressionable child star Melanie Griffith started dating 22-year-old Don Johnson. It's hard to believe that something so undeniably inappropriate (and not to mention illegal!) was allowed to fly under the radar for as long as it did. But, that's Hollywood, folks. Unsurprisingly, their first marriage deteriorated quickly after only six months. By then the relationship had spiraled into a drug-fueled haze. After a couple of years of therapy, Griffiths acknowledged her “addictive personality" traits — however, she reconnected with Johnson in 1988 and the pair married for a second time, only to divorce again.

Sean Penn could have easily appeared on this list more than once, but it's his stormy relationship with Madonna that we remember most. Far from a perfect match, the entirety of their relationship was marred by accusations of infidelity and domestic violence — not to mention a brief stint in jail which Penn served after a physical altercation with a photographer who was hot on their tail. With their contrasting egos and quick tempers, Penn and Madonna seemed doomed to fail from the start, with some reports claiming that the pop star's inner circle loathed the Oscar-winning actor, likening him to a spoiled brat. We wonder if Robin Wright would agree?

Although he's back in the spotlight for his golf prowess, there was a significant stretch of time where Tiger Woods' domestic situation got more media play than any of his record-breaking athletic achievements. Not that we feel sorry for him, or anything. In 2009, the National Enquirer dropped a bombshell that left the sports world reeling. It turned out Woods had been cheating on his Swedish-born wife, Elin Nordegren, with a New York City nightclub manager. It only got worse from there as dozens more women stepped forward claiming they'd had affairs with golf's hottest commodity, leading to lost sponsorship deals from the likes of Gatorade and AT&T. In a TV apology Woods said, "I thought I could get away with whatever I wanted to." Nordegren, for her part, was ready to move on and was granted divorce and custody of the couple's two kids in 2010.

Although married to his first wife at the time, renowned playwright Arthur Miller embarked on an affair with Marilyn Monroe in 1955. The duo married the following year and, while they appeared to adore one another in public, there were plenty of problems behind closed doors – including a series of notes Monroe happened upon in which Miller wrote disparagingly about his wife and their "disappointing" marriage. Adding to the overall tension were Monroe's two failed pregnancies, for which she received little emotional support from Miller. The actress, by this point, had become addicted to pills and retaliated against Miller's lack of interest by having an affair with costar Yves Montand. The plan ultimately backfired as Miller shrugged off his wife's infidelities. The ill-matched pair filed for divorce in 1961. The following year, Miller didn't even attend Monroe's funeral.

Consider this more of an honourable mention: From the "Billy Bob" tattoo to the vials of each others' blood they wore around their necks, it's no wonder that the three-year marriage between Billy Bob Thornton and Angelina Jolie garnered so much media attention. They were weird. But were they toxic? By all accounts they were genuinely in love with one another and, to this day, speak highly of each other and their time together. (Which is more than we can say about Jolie and Brad Pitt.) While some were a little weirded out by their 20-year age gap and penchant for public displays of affection (if you'll recall, there was a lot of tongue, in hindsight they don't seem as poorly matched as they did when they first exchanged vows back in 2000.