The Hottest-Mess Actor Couples Ever
This feature references substance misuse, addiction, domestic violence, and allegations of child abuse.
There once was a time when celeb romances were shrouded in mystery, presented to the public as pristine and glamorous with no suggestion of anything untoward bubbling beneath the surface. It was thus left to biographers to detail the true nature of those relationships and all the mess and tumult that followed. But in the social media age, celebrities' lives are quite literally on display for all to see.
The days of intrigue are replaced by oversharing, PDA-packed snaps, and, in some cases, even post-coital selfies. In many ways, this openness has helped fans feel closer to their favorite celebs. But in some instances, the oversharing gets so extreme that the public has to practically beg the Insta snap-happy stars to just ... stop. Please?
When it comes to actor couples, there's a particular sort of messiness involved. To begin with, acting often attracts larger-than-life individuals, so pairing two actors together gives a double whammy of disarray, not to mention a clash of egos. It's perhaps for this reason that many stars opt to date folks outside of their profession. But for those who do date other actors, it's often a recipe for disaster. For every wholesome couple who have been hopelessly devoted to each for decades, there are the ones who have faced endless cheating scandals, public screaming matches, and the spilling of deets. If being a hot mess is lit, then these folks are on fire. Can you handle the heat? These are the hottest-mess actor couples ever.
Harry Styles and Olivia Wilde's worrisome fling
The "Don't Worry Darling" drama will no doubt go down in pop culture history as the mess to end all mess. Production for Olivia Wilde's sophomore directorial offering began in 2020. It initially starred the controversial Shia LaBeouf, who was soon replaced by Harry Styles in September. The "Watermelon Sugar" singer's casting appeared to coincide with Wilde's split from her partner of almost a decade, Jason Sudeikis. By January, Wilde and Styles were dating, making this timeline appear rather iffy. "Everyone saw it coming. During breaks, he hasn't been able to stay away and visited her trailer," a source told People. The Harry stans did not want their beloved One-Directioner-turned-actor dating Wilde, resulting in her receiving a barrage of hate online.
The real drama began when Wilde was served with custody papers from Sudeikis when she was promoting her flick at CinemaCon. "We have never in the history of the convention had an incident where a delegate has approached the stage who was not authorized to be there," said CinemaCon, per Deadline.
Matters were further complicated by an alleged feud between Florence Pugh and Wilde. The director's fury was rumored to have been prompted by Styles having previously kissed his leading lady off-screen, per The Sun. Wilde told Variety that the feud rumors were pure fabrication. But, the damage was seemingly done and Wilde and Styles ended their romance in November 2022. Truly, this was one Wilde ride!
TomKat was a hot mess from the start
Almost twenty years later and we are still pondering the all-important question: Why did Tom Cruise jump up and down on Oprah's couch? Back in 2005, Cruise appeared on "The Oprah Winfrey Show" to promote his new film "War of the Worlds," but the interview quickly turned into a debacle that would be forever etched into the legend of memedom. The audience was whipped up into a Beatlemania-esque frenzy as a grinning Cruise waltzed on stage. Later, he inexplicably began jumping on Winfrey's furniture to profess his love for girlfriend Katie Holmes.
But Cruise and Katie's relationship was anything but a fairytale. A Vanity Fair profile revealed that her father, Martin Holmes, didn't want his daughter to marry Cruise and allegedly concocted a plan to have her labeled a suppressive person by the Church of Scientology. But by this point, Holmes was already pregnant with the couple's daughter, Suri, and the wedding went ahead. Scientology whistle-blower Leah Remini alleged that Cruise forbade his bride from nursing their baby on the big day, instead leaving Suri to cry on the floor, per Daily News. There were also rumors that Cruise was keeping his wife hidden from the public.
In 2012, the "Top Gun" star was said to be blindsided when Katie filed for divorce. She was apparently well prepared. Her father, a divorce lawyer, was alleged to have negotiated a strategic prenuptial agreement for her. Three years later, the exes were rumored to no longer speak to each other.
We learned about Kristen and Dax against our will
Pretty much from the outset of their relationship, Kristen Bell and Dax Shepard have proven themselves the reigning champs of oversharing. For instance, when Bell gave birth to the couple's first child, Shepard tweeted (via Today), "Lincoln Bell Shepard is here. She has mom's beauty and dad's obsession with breasts. Hooray!"
Nothing is sacred with these two. We even learned (against our will) that the couple schedules sex sessions. "You're like, 'I know you're tired, but it's been two weeks, so we really got to get to it,'" Bell told Self in 2021. Then came the infamous moment when they decided to disclose that they rarely bathe their children. "I wait for the stink. That tells you when they need to bathe," Bell half-jokingly told "Daily Blast LIVE." Meanwhile, Shepard also admitted that he doesn't necessarily bathe until he gets really smelly. Ick.
Appearing on her husband's "Armchair Expert" podcast in 2022, Bell confessed that the couple's two children, then aged 7 and 8, still sometimes sleep in the same bedroom as them — but only on the floor. "A few nights ago I began to smell a really raunchy smell. And I'm like, 'Who's farting?'" she recalled. It turned out that Shepard and the kids were all releasing gas. She also told Today that she lies to her children about when their birthdays are, something that she perhaps picked up from the Homer Simpson school of parenting.
Liz Taylor and Richard Burton went for round two
When it comes to old-school Hollywood romances, Richard Burton and Elizabeth Taylor had it all. She was a society gal who loved nothing more than to be draped in furs and jewels, he was a humble Welshman who preferred fish 'n' chips to caviar and wine. What could possibly go wrong?
"She was a dark unyielding largess. She was, in short, too bloody much," Burton said upon first setting eyes on Taylor, per the book "Furious Love: Elizabeth Taylor, Richard Burton, and the Marriage of the Century" (via Vanity Fair). And it turned out that Burton could have too much of a good thing. He and Taylor began an affair after falling in love on the set of "Cleopatra." Tying the knot in 1964, they immediately became a notorious tabloid staple.
Then came the excess and extravagant spending — Burton famously lavished his lady love with ostentatious diamonds, including a $1.5 million Cartier ring. But the relationship grew tumultuous, blighted by arguing and substance misuse (they famously enacted their marital turmoil in "Who's Afraid of Virginia Woolf?"). After divorcing in 1974, they walked down the aisle again in 1975. They parted ways for good a year later, with Burton dying in 1984. Despite the calamity, Taylor said that if her ex-husband hadn't died, she would likely married him for a third time. "The highs were too high," she told Barbara Walters. "It was almost like ... we loved each other almost too much."
If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).
Steve Coogan was one of Courtney Love's greatest shames
Though principally known as a musician, Courtney Love has won acclaim for acting in several high-profile films, including "The People vs. Larry Flynt" and "Man On the Moon." A headstrong and outspoken rock icon, Love seems quite the unlikely match for Steve Coogan, the man who gave us the cult comedy character Alan Partridge. Yet, the pair dated in 2005, to the surprise of absolutely everyone.
At the time, the News of the World (via The Guardian) claimed that Love was pregnant with Coogan's child following a two-week fling. She was apparently embarrassed by her rendezvous with the TV funnyman, which coincided with her decision to seek help for substance misuse. "What does it make me look like that I have slept with Alan Partridge?" the tabloid quoted her as telling a friend. "Given the A-grade stars I've dated it's embarrassing. I mean ... Alan Partridge!" These pregnancy rumors turned out to be untrue.
By Love's own admission, the fleeting romance was nothing short of a hot mess — and far from romantic. "All it was, was a couple of shags at the Sunset Marquis and I did not know he was Alan Partridge," she told Love Magazine (via Evening Standard) in 2013. Charming. In a since-deleted Instagram post, she later branded the affair one of the greatest shames of her life, along with taking crack. Such sentiments couldn't have delighted Coogan. In the words of his comic alter ego, "That's saaaad!"
If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).
Charlie Sheen and Denise Richards' disastrous marriage
Charlie Sheen's love life has unfortunately been nothing short of disastrous. From allegedly shooting his ex to his various domestic violence arrests and being accused of exposing partners to HIV, Sheen clearly has a long checkered history with women. So, his marriage to Denise Richards was, admittedly, never going to be smooth sailing. When the Bond girl wed the Hollywood bad boy in 2002, it appeared as though Sheen had finally settled down, and he commemorated the occasion by tattooing his new bride's name on his wrist. But the honeymoon period would soon be over.
While pregnant with the couple's second child in 2006, Richards filed for divorce. In court documents obtained by TMZ, she accused Sheen of domestic violence and alleged that she caught him watching pornography starring what appeared to be minors. Sheen denied the claims, arguing that his wife was instigating a smear campaign against him.
A decade later, the bad blood continued between the exes. In 2015, Sheen went on a bizarre Twitter rant (via Us Magazine) against Richards on Father's Day in which he attacked her parenting skills and unleashed a slew of obscure slurs against her. During an appearance on the "Divorced Not Dead" podcast, Richards opened up about the pair's toxic marriage. "The behind-the-scenes stuff was way worse than what was out there," she conceded. Later, she added, "It was really bad ... I said to myself, 'Would I want my daughters to be married to this man?'"
If you or someone you know may be the victim of child abuse, please contact the Childhelp National Child Abuse Hotline at 1-800-4-A-Child (1-800-422-4453) or contact their live chat services.
If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.
Sienna Miller and Jude Law didn't know when to quit
Back in the 2000s, Sienna Miller and Jude Law were peak British gorgeousness. With their chiseled jawlines (in the seemingly innocent days before the dreaded buccal fat removal) and impossibly posh accents, we were all rooting for them. But what started out as oh-so-good turned out to be oh-so-messy.
From the outset of their romance, which began after they met on the set of "Alfie" in 2003, Miller and Law became tabloid fodder. "We love each other desperately, and it makes me sad that the press are so cruel and negative," Miller told Vogue (via People) at the time. The couple announced their engagement two years later after Law proposed on Christmas day. Things quickly went downhill after that.
Just months after announcing their engagement, Law was caught cheating on Miller with his children's nanny, Daisy Wright. To make matters worse for Miller, the staff member decided to spill the tea to the press. "It was amazing," she told The Mirror. "Jude was a masterful lover who made my whole body tingle." Big yikes. She also revealed that one of Law's children had walked in on the pair having sex. Then came an apology from Law, followed by a reconciliation, then a break-up, and another reconciliation in 2009. They broke up for good two years later. Discussing the cheating incident with Rolling Stone (via People), Miller declared, "Monogamy is a weird thing for me ... because, let's face it, we're f***ing animals."
Ava Gardner and Frank Sinatra's marriage was one bumpy ride
When a smoldering Hollywood bombshell known for her femme fatale roles crosses paths with the toughest guy in town, sparks are bound to fly. As such, the marriage between Ava Gardner and Frank Sinatra has become the stuff of legend.
According to the book "Ava Gardner: Love is Nothing" (via Vanity Fair), Sinatra, who was married, began an affair with the star in 1949. Sparks — and bullets — flew on the pair's drunken first date, which ended with them shooting out street lights and store windows before being stopped by the police (20th Century Fox allegedly bribed the cops to let the A-listers off). At the time, the pair's forbidden rendezvous did not go down well with their peers, with Grace Kelly once remarking, "Ava is such a mess it's unbelievable." But it was the shared mess that drew the lovers together and they wed mere days after Sinatra divorced his wife in 1951. In true diva fashion, Gardner inflamed the media attention by remarking on her hubby's, ahem, endowment in relation to his slight frame.
Unsurprisingly, the marriage was highly tumultuous. Both Sinatra and Gardner had foul tempers, and they frequently engaged in loud screaming matches. "[We] were high-strung people, possessive, jealous, and liable to explode fast," Gardner said, per James Kaplan's book, "Frank." "When I lose my temper, honey, you can't find it anyplace ... He's the same way." This volatile relationship simply wasn't sustainable and Gardner filed for divorce in 1954.
Angelina and Billy Bob were peak Y2K hot mess
Billy Bob Thornton may not be too keen on featuring in this rundown. This is, after all, a man who once vehemently objected to being called an actor, despite being ... an actor. But he and Angelina Jolie were undoubtedly one messy power couple making their mark on Y2K culture.
The acting duo were married from 2000 to 2003 and were renowned for oversharing, having discussed their sexual escapades in detail to the press. And, of course, there was the matter of their infamous blood necklaces and the rumors they had a love dungeon. During a talk at Loyola Marymount University's School of Film & Television in 2014 (via The Hollywood Reporter), Thornton addressed the controversy surrounding his relationship with Jolie. "That whole time was quite a whirlwind," he reflected, before clarifying that the dungeon rumors were false, while the blood vials were very much real — though exaggerated by the media.
Jolie was 24 when the couple got married — twenty years younger than her groom. Quite notably, Thornton was also engaged to Laura Dern at the time of their union, and the "Jurassic Park" star was reportedly blindsided by the news. Speaking to Elle, Jolie discussed the backlash she faced at the time. "It wasn't a need to be destructive or rebellious," she explained. "It's that need to find a full voice ... It may come out very strange, it may be interpreted wrong, but you're trying to find out who you are."
Ben Affleck and J-Lo's roller-coaster romance
There are, of course, now two Bennifers. But the Bennifer that goes down in pop culture infamy is the one that immediately conjures the words "Gobble, gobble." Yes, Ben Affleck and J-Lo were the hottest of hot messes in the aughts, but few predicted that this particular portmanteau would be resurrected decades later.
In 2002, the pair met on the set of the widely panned bomb "Gigli," in which Affleck affects a stereotypical Italian-American mobster accent and Lopez plays a lesbian who inexplicably agrees to sex with a man. Truly, the 2000s were a problematic era. Then, Affleck appeared in J-Lo's music video for "Jenny From the Block," famously kissing her derriere. Following "Gigli's" release, a media frenzy erupted and the couple found themselves plastered on tabloids all over the country. All the while, their respective movie careers suffered. "I was actually in the very worst position you can be in in this business, which is you can sell magazines but not movie tickets," Affleck told The Hollywood Reporter. After an engagement and another flop thanks to "Jersey Girl," the couple split in 2004.
But, fast forward eighteen years, and all hail Bennifer 2.0. Having wed in 2022 after a brief reconciliation, Affleck and Lopez continue to generate headlines, not to mention memes. Notably, the couple went viral at the 2023 Grammys after Affleck was snapped looking bored. Reclaiming the negative publicity, Lopez poked fun at her hubby's sullen countenance on Instagram, proving that the memed can become the memer.
Will and Jada spilled the deets no one wanted to hear
For many years, Will Smith and Jada Pinkett seemed like a sweet and wholesome power couple (not to mention chic — lest we forget those fire twinning ensembles of the '90s). But social media is arguably the worst thing that ever happened to these two ... Well, that and The Slap, but that's a story for another day.
In a 2020 episode of Pinkett's Facebook series "Red Table Talk," she infamously divulged that she had been seeing another man. What made this clip go viral was the fact that she disclosed this information in the presence of her husband, who was a guest on the show. At one point, Smith stated that the affair is nobody's business ... then proceeded to discuss said business. "I got into a different kind of entanglement with August," Pinkett said in reference to rumors that she was having an affair with August Alsina, who is 21 years her junior (she and Smith were separated at the time). She also said that the relationship was the first time in ages that she actually felt good. Ouch.
Moreover, in his 2021 memoir, "Will," Smith divulged that he and his wife went to a tantric sex expert to help mend their marriage. During one session, he confessed that he wanted a harem of women, which included Oscar-winner Halle Berry and ballerina Misty Copeland. All this oversharing has led to a Change.org petition begging the couple to stop discussing their sex life.
Tori Spelling and Dean McDermott left us bewildered
There's no end to the messiness that is Tori Spelling and Dean McDermott. The pair found themselves in the spotlight after it was revealed that McDermott cheated on Spelling in 2014 with 20-something Emily Goodhand. His one-time lover ended up spilling the deets to Us Magazine, stating, "He told me he and Tori had a sexless marriage. I believed him."
Rather than keep the matter private, McDermott decided to explain exactly why he cheated on his wife on the "Daddy Issues" podcast (via TooFab). "For me, it wasn't about [Tori], it was about inadequacies with myself," he confessed. "I felt so bad about myself, I felt like a piece of s***, I needed to do that to feel some kind of power." Moreover, Spelling brought her daughter into the proceedings. "My daughter saw something and it really upset her," she told the "Women on Top" podcast regarding the couple's negative publicity. "She said, 'Daddy, I saw something online that said that years ago you cheated on mommy.'" While she acknowledged that her daughter was too young to be told the truth about the affair, she said that she was prepared to tell her what really went down one day.
Since then, things have been increasingly messy with these two. In 2023, divorce rumors began swirling, only to be quashed when Spelling posted Instagram snaps of McDermott having a family dinner with the couple's kids. As of this writing, sources told Entertainment Tonight that the couple was undergoing marriage counseling.
Anjelica Huston put up with Jack Nicholson's nonsense
After meeting at a party in 1973, Anjelica Huston and Jack Nicholson entered a whirlwind romance that lasted almost 20 years. Although the two were madly in love, their relationship was highly tumultuous. For instance, Huston longed to marry her long-term boyfriend, but when she brought up the matter, he brutally shot her down. "He said, 'Marry you? Are you kidding?'" Huston recalled in her memoir, "Watch Me." "I wept all the way back to L.A. and sobbed for three more days after that. Jack just didn't get it."
Nicholson cheated on Huston throughout their relationship. The actor admitted to his numerous infidelities in an interview with Vanity Fair, boldly declaring, "Of course, I lied to her. It's the other woman I would never lie to." Matters were further complicated when Nicholson got one of his many other women, Rebecca Broussard, pregnant. This was particularly painful for Huston, who longed to be a mother but couldn't conceive. Discussing the debacle with Parade (via HuffPost), Nicholson revealed that when she found out, a furious Huston marched onto the set of one of his movies and attacked him. "Anjelica can punch!" he recalled. "Meanwhile, Rebecca [Broussard] didn't want me to separate from Anjelica. Well, they both have good taste."
Brazen as Nicholson may be, Huston eventually gave up hope of trying to change her cad lover and the pair called it quits in 1989. Pals have since expressed their fears to Radar that Nicholson will die alone.
If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.
Ewan McGregor and Mary Elizabeth Winstead's off-set drama
Ewan McGregor long seemed like the boy next door. The affable Scottish actor won scores of fans for his roles in "Star Wars" and "Moulin Rouge." So when rumors swirled that he was cheating on Eve Mavrakis, his wife of 22 years, the public was aghast. In 2017, The Sun published snaps of McGregor locking lips with his "Fargo" co-star Mary Elizabeth Winstead, who is 13 years his junior, at a trendy London eatery. Soon after the photos were leaked, he broke up with Mavrakis and went public with Winstead.
To make matters messier, his daughter, Clara, had some strong words for him and his lover. After Clara posted a photo of her mom sunbathing on Instagram (via The Mirror), a fan remarked that the attractive Mavrakis likely has numerous male suitors. Clara replied, "Nah I keep her away from a**hole men who leave my goddess of a mother." Then, she turned her attention to Winstead. Commenting on a fan page that suggested the actor was beautiful, an increasingly shade-throwing Clara wrote, "Most beautiful and talented woman on earth? Oh man, y'all are delusional. The girl is a piece of trash." Oof.
Despite his daughter's apparent reservations, McGregor went on to have a son with Winstead, whom he wed in 2022. Discussing the drama with GQ, he said, "A divorce in a family is a bomb going off in everyone's life." And a bomb it was. Choose life? More like choose chaos.