There is no paucity of romances gone wrong, sour or otherwise positively suicidal (namely, Romeo and Juliet) in the annals of human history. As such, maybe it’s best to keep it narrowed down to some of the more memorable toxic relationships and breakups of the twenty-first century in honor of Valentine’s Day, since this century so rarely gets much love anyway. What follows are this epoch’s most standout bad romances (with many still excluded from the final cut).
Amy Winehouse and Blake Fielder-Civil: In so many ways, this is the most tragic of the tainted loves mentioned on this list, for it ultimately cost Amy Winehouse her life. As she went down the rabbit hole of l’amour fou, Fielder-Civil a lowly bar troll who feigned being some kind “scene insider,” ended up setting in motion all the songs for 2006’s Back to Black before breaking Amy’s heart yet again by dumping her for his ex (and then getting back together with Amy just in time for her fame crest). His destruction of her heart was not just through introducing her to more drugs, but also by getting sentenced to jail time and leaving her to drink and drug on her own as she tried to figure out where it all went wrong. Although there was a period of sobriety that came with her “St. Lucia phase,” Winehouse again fell prey to addiction before her final concert in Serbia. And, as you know, we never got a right proper album from her again (because Lioness: Hidden Treasures really doesn’t count).
Britney Spears and Kevin Federline: It’s only natural that the singer of “Toxic” should appear on this list. And while Justin Timberlake might be the more obvious choice, Britney’s collateral damage in tying herself to K-Fed was far worse. Because Federline was one of the biggest snakes involved in setting her up to fail in such a way so that she could somehow be deemed “worthy” of a conservatorship. What’s more, her illustrious head shaving incident paired with the umbrella outburst—the one that will forever haunt Britney in paparazzi images no matter how far she’s come from that moment—was a direct result of K-Fed withholding her own children from her. Trying to paint her as “unstable” because of her addictions to alcohol and drugs. Yes, Kevin Federline was accusing someone else of being unstable. And in a classic instance of proving patriarchy always wins, Britney was condemned for wanting to spend a few extra moments with her youngest child, Jayden, by taking him into the bathroom of her house so that someone from Team Federline couldn’t yet cart him away during their visit. One wouldn’t be surprised if it was Federline himself who called the police on Britney as part of the vast conspiracy against her to get her 5150’d.
Lindsay Lohan and Samantha Ronson: Another “hot mess” icon of the 00s, Lindsay Lohan, dated many men throughout the decade, but it wasn’t until linking up with Samantha Ronson in 2008 that Lohan began to show the full extent of her passions. Still heavy into the drinking and partying scene (despite her numerous rehab stints), Lohan’s emotions were running high throughout her relationship tenure with Ronson. This, paired with Ronson’s tendency to incite jealousy with her nightlife-oriented career, seemed to activate all the stalker-y, clingy characteristics within Lohan, who even moved next door to Ronson after the end of the relationship. Ronson, incidentally, had changed her locks.
Brad Pitt and Angelina Jolie: While Brad Pitt and Jennifer Aniston could also make the list, the two have actually remained rather close in spite of Pitt’s dastardly infidelity—perhaps what some would call karma against Jolie. And if that’s the case, then maybe Pitt’s own karma was his nasty divorce from the actress-turned-humanitarian, a relationship sprung from stepping out on his own previous marriage. And with a gaggle of children involved, paired with Jolie’s perhaps overly protective maternal nature, things haven’t been easy amid the custody battles that have followed, as well as accusations of Pitt’s abusiveness and alcoholic predilections (how Ben Affleck).
Katie Holmes and Tom Cruise: As one of the most bizarre romances of the 00s—complete with Cruise essentially shouting, “I’m straight! I’m straight! on Oprah’s couch—it was bound to end sooner or later. Even in spite of Scientology’s hold over Holmes, like contractually. The marriage ended in 2012, with Cruise being surprisingly quick to reach a divorce settlement—likely in a bid to keep their names out of tabloids as soon as possible. Part of the settlement included Katie gaining primary custody of their lone child, Suri. With Cruise getting “generous visitation” rights. Sounds sinister. Like the entire dynamic.
Ben Affleck and Jennifer Garner: Another woman who got the fuzzy end of the lollipop in choosing to marry an irascible actor was Jennifer Garner. After a lengthy marriage (in Hollywood time), the two seemed to “inexplicably” divorce, a move initiated by Garner in 2015, amid rumors of Affleck’s infidelity with their nanny, as well as his bout with alcohol addiction. The divorce was called off briefly before being back on in 2017, subsequently finalized in 2018. In 2020, before Bennifer was rebooted, Affleck called the divorce “the biggest regret of my life.” Or was it all what J. Lo would describe as being “on my way to you” with a thirteen-year detour?
Jude Law and Sienna Miller: Mirroring the Affleck/Garner trajectory in many ways, Law and Miller also met on the set of a movie in 2003, specifically the remake of Alfie. After a year of dating, the two were engaged in 2004. But perhaps Miller should have been wary of a too-long engagement, for it gave Law ample opportunity to cheat on her with his children’s nanny (proving, yet again, all the reasons why you shouldn’t go for a man who has already spawned). The news broke in ’05 and the two soon called it quits before reuniting again in ’09, dating for about another year before ending it the final time in February of ’11. But at least they’ll always have that middling 00s movie together. Their “child,” if you will.
Sandra Bullock and Jesse James: Together from 2003-2010, Bullock already made a rookie move in deciding to marry a commoner (something Britney also made the mistake of doing—twice), because, no, being a motorcycle builder and on Monster Garage doesn’t count as “famous.” It wasn’t until ’05 that they were actually married, whereupon James proceeded to cheat with gusto on his wife. Amid the process of adopting a child together, Bullock went on to adopt said child as a single parent—in a maneuver that echoed Jennifer Garner as Vanessa Loring in Juno.
Rihanna and Chris Brown: Before she was known as an empowered woman and the billionaire queen of a beauty and lingerie empire, Rihanna took a wrong turn somewhere around 2009, when she had just achieved meteoric pop star status with Good Girl Gone Bad—which was so successful it got a reissue called Good Girl Gone Bad: Reloaded. The album that came out later in 2009, Rated R, seemed a vast departure from her previous music. Darker, tinged with a more “seen it all,” “treat me rough” aura. There’s no denying Brown’s treatment had something to do with that. And yet, even after being assaulted by him, Rihanna, like so many victims of domestic violence, decided to go back for more circa 2012, even collaborating with him on a song from Unapologetic called, um, “Nobody’s Business.” In the end, Rihanna perhaps came to her senses and put a stop to Brown’s existence in her life by early ’13.
Gwen Stefani and Gavin Rossdale: Something about nannies, isn’t there? And there was certainly something about Mindy Mann for Gavin Rossdale, who carried on a three-year affair with her as Gwen tried to ignore the signs, at times distracted by being pregnant with their third child and all. But maybe not all nannies are sordid minxes, as it was another one in the household who tipped Gwen off to an explicit text exchange that showed up on a family iPad linked to Rossdale’s iPhone [Gavin shakes fist at Steve Jobs here]. The divorce led to Gwen writing one of the most emotional tracks, “Used to Love You,” from her 2016 album, This Is What the Truth Feels Like. And, of course, to turning rather country as she molded her post-divorce reinvention in honor of her new boo, Blake Shelton. Not coincidentally, a vast divergence in type from Rossdale.
Madonna and Guy Ritchie: It took Madonna four years to fully realize her sentiments toward her emotionally and financially brutal divorce with Guy Ritchie in 2008. A contempt and sense of betrayal that would manifest sonically on 2012’s underrated MDNA. While on a world tour to promote Hard Candy with the Sticky & Sweet Tour, news of the divorce broke, with Madonna famously not having a prenup in place to prevent Ritchie from taking roughly eighty million dollars in the settlement. Madonna even chose the same divorce lawyer as Paul McCartney did when he broke it off with Heather Mills—who also evaded signing a prenup. Such is the naivety of trying to believe in love that lasts “forever.” Ultimately, it prompted Madonna to offer some of the most personal lyrics of her career on MDNA, including the ones on “Love Spent,” during which she bemoans, “I want you to take me/Like you took your money/Take me in your arms/Until your last breath/I want you to hold me/Like you hold your money/Hold on to it till there’s nothing left.” Including her son with Ritchie, Rocco, who fled to London during another tour of Madonna’s (Rebel Heart) to assert his preference for living with him instead. Ah, the sting of the Ritchie men.
Miley Cyrus and Liam Hemsworth: As roller coaster-y as one would expect of a relationship with a Sag like Miley, these two were together on and off for ten years after meeting on the set of The Last Song—spurring yet another anthem created by heartbreak, 2013’s “Wrecking Ball.” The duo eventually married in 2018 (engaged for the first go-around in 2012), only to divorce by January 2020. Cyrus quickly went from singing a song like 2017’s “Malibu” (“We watched the sun go down as we were walking/I’d spend the rest of my life just standing here talking”) to 2019’s “Slide Away” (“Once upon a time, it was made for us/Woke up one day, it had turned to dust/Baby, we were found, but now we’re lost/So it’s time to let it go”). Such is the impetuosity of a girl who loves you one minute and then tweets, “I wanna see the new Hunger Games but that means I’ll have to look at my ex for two fucking hours” the next. But again, it’s definitely generated some real bangerz as a result.
“Nils Sjoberg” a.k.a. Taylor Swift and Calvin Harris: Ah, and speaking of a bangerz queen… Of course, Taylor has many exes to choose from—a fact she hates jokes being made about—but arguably the least amicable split, creatively speaking, was the one from Calvin Harris (sorry, Jake). After fifteen months together that seemed to start all too well (complete with that illustrious Instagram declaration of their relationship on a giant inflatable swan together), things went south for the musical pair. Particularly after Harris went on a Twitter tirade about Swift wanting to claim credit for the song they worked on together, “This Is What You Came For.” Initially intended to be sung by Swift, the track was taken over by Rihanna (another member of this breakup list). In response, Harris raged, “I figure if you’re happy in your new relationship you should focus on that instead of trying to tear your ex bf down for something to do. I know you’re off tour you need someone new to try and bury like Katy ETC but I’m not that guy, sorry. I won’t allow it.” He also stated, “Hurtful to me at this point that her and her team would go so far out of their way to try and make ME look bad at this stage though.” Oh hell no, this is not what Swift came for.
Johnny Depp and Amber Heard: In what has become a classic case of “he said, she said,” the libel lawsuit that has also arisen out of Depp and Heard’s divorce proceedings adds a fresh layer of bad blood and poisonous venom to the entire affair. Depp, to his surprise, eventually lost the libel case against The Sun (even after appealing), which branded him as a wife beater, in what can be referred to as “Oscar Wilde Luck.” All while Depp and his team continue to call into question Heard’s testimonies and accounts of her years spent with Depp, whose abuse occurred mostly while he was under the influence of alcohol or narcotics. Depp and his legal counsel have further accused that Heard is embellishing what transpired, as well as omitting details of her own abuse toward Depp. The war continues to be waged, with Heard recently calling out Depp for trying to conspire against her to get her fired from Aquaman and the Lost Kingdom after Depp himself was fired from the Fantastic Beasts franchise in the wake of the courts ruling in favor of The Sun re: that wife beater branding. Ain’t love grand?
Robert Pattinson and FKA Twigs: Although Pattinson might have been gentler than Shia LaBeouf, it was still through this relationship that Tahliah Debrett Barnett a.k.a. FKA Twigs endured some of her most brutal verbal abuse via online comments directed at her from Pattinson’s fans. As Twigs would later describe it, “People just called me the most hurtful and ignorant and horrible names on the planet. He was their white Prince Charming and they considered he should be with someone white and blonde.” As other female musicians before her, Twigs would channel this pain into a song like the heart-wrenching “cellophane,” from 2019’s Magdalene.
Kanye West and Kim Kardashian: As the freshest celebrity romance schism of this past year, Kanye has provided no shortage of headline-grabbing moments when it comes to exhibiting a very, “If I can’t have her, this basic white boy can’t” philosophy. As Kanye continues to publicly humiliate himself and Kim—as well as their children—with his rantings, it makes one wonder if Kardashian feels that marrying Ye to elevate the tier of her celebrity echelon was all worth it. Something Davidson will likely be asking himself if he ends up marrying Kim.
Pete Davidson and Ariana Grande: Don’t forget that Pete wasn’t exactly “polite” after the Ari breakup. Not only did he devote an entire comedy special to lambasting her solely because he was bristled by “thank u, next” and the accompanying album of songs mostly about him, but because Grande was candid enough to call it like it was and say, “It was frivolous and fun and insane and highly unrealistic, and I loved him, and I didn’t know him.” As for Pete, he made the vow, “I’m not dating for a while. Unless I meet the love of my life…” So that must mean Kate Beckinsale and Kaia Gerber and Margaret Qualley and Phoebe Dynevor all qualified before this Kim Kardashian phase. Meanwhile, Ari is married to a Davidson lookalike and singing about the best sex of her life. The winner is clear.
Maddy Perez and Nate Jacobs: As the only fictional couple to make the cut on this list, you know Maddy and Nate from Euphoria must warrant some very special bad romance circumstances in order to show up here. Not only because of the toxicity the two bring out in one another, but the fact that violence and venom is the norm in their dynamic, with Maddy repeatedly stating she’s not sure she would be able to “enjoy” a relationship of any other variety. Nate’s own physically abusive tendencies reached a crescendo in the February 13th episode, “A Thousand Little Trees of Blood,” wherein he breaks into her room with a gun in hand, watches her undress and then pretends to play Russian roulette on himself so he can extract an incriminating disc of his father having sex with the underage Jules (Hunter Schafer). And yeah, that last statement should give you some clue as to why he’s so fucked up.
With the twenty-first century likely stamping out humans and, with them, so-called “conventional” versions of love altogether, this could very well remain a somewhat definitive list even as time wears on. And the AI takes over. Oh wait, should Grimes and Elon have made the cut, too?
