The Chaotic Celebrity Couples That Got Us Through 2021, Ranked

The Year of Our Lord 2021 has been cursed in almost every conceivable way—and in these troubled times, we’ve all been forced to develop some (more) coping mechanisms. Personally, watching the same three TV shows on a loop and trying to set a new record for pizza consumption got me through 2020, but I’ve found that this year has slowly pushed me toward a deeper relationship with my chosen religion: chaotic celebrity couples.

I’ll admit that I’ve become something of a lapsed Chaothlic over the years, but 2021 has been such a goldmine of jaw-dropping hookups and bizarre publicity stunts that I’ve found myself tithing, once more, to the Church of People Magazine. There was the tabloid-fueled journey from BenAna to Bennifer; Megan Fox and Machine Gun Kelly have been making out everywhere, sometimes alongside their coupled BFFs Kourtney Kardashian and Travis Barker; and remember that time Dominic West and his wife held that weird makeshift press conference on their front lawn, complete with a handwritten sign attesting to the health of their marriage, after he was spotted making out with Lily James? Wild stuff that somehow, yes, all did happen this year, even if it now feels like a decade ago. And we haven’t even mentioned Rita Ora and Taika Waititi.

Has it been a record year for celebrity messiness, or are we all just more bored and desperate for any news that’s entertaining rather than depressing? Whatever the reason, these surprising A-list flings have somehow gotten all of us gossip lovers through another devastating year. But which of them has been the most fun? See our ranking below, from least to most entertaining.

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Olivia Munn and John Mulaney

As instantly viral as the Munnlaney mishegas might have been when the news first broke this spring, a lot of fans’ reactions were both bizarre and disappointing. It seems a significant portion of Mulaney’s fans believe they somehow know him well enough to judge his choices—from getting a divorce, to meeting someone else (Munn), to having a child.

Mulaney has spent years telling jokes about his struggles with addiction; they appear in most, if not all, of his stand-up routines. When news of the comedian’s relapse and subsequent choice to enter a rehabilitation program first broke, everyone—media and fans alike—seemed determined to get their responses “right.” But linking up with Munn appeared to take things a bridge too far; the internet largely turned on Mulaney, framing Munn as an interloping Angelina Jolie and his ex-wife, Anna-Marie Tendler, as a betrayed Jennifer Aniston.

As fun as celebrity gossip can be, the controversy surrounding this relationship has been a glaring reminder that fans can never really know the A-listers we idolize—and that, even so, many will cast judgment on their supposed “faves” should they dare fall off the pedestal.

Megan Fox and Machine Gun Kelly

Yes, technically these kids got together in 2020—but how could we leave them off the list when this was the year that gave us “I am weed”?

This year took Megan and MGK to new heights. They kicked off 2021 with engagement rumors—which Fox countered with an Instagram Story depicting a ring inscribed with the phrase “Fuck you.” They made out in a bathroom at the VMAs next to Kourtney Kardashian and Travis Barker. (More on that chaotic couple in a moment!) They talked about giving each other vials of blood and gave that instantly iconic British GQ interview in which Fox described their surreal first encounter.

“I just remember this tall, blond, ghostly creature, and I looked up and I was like, ‘You smell like weed,’” Fox recalled. “He looked down at me and he was like, “I am weed.’ Then, I swear to God, he disappeared like a ninja in a smoke bomb.”

Was the strange remark that inspired a thousand couple’s costumes a Salvador Dali reference or just stoner talk? You decide!

Sure, this couple’s incessant testimony about their “twin flame” connection is getting a little overdone—and yes, it’s frequently tied up in various publicity efforts, including his music videos and that steamy Skims campaign that featured Fox and Kardashian. But what can I say? The last two brain cells rattling around in my skull still love to see it.

Chrishell Stause and Jason Oppenheim

Say it ain’t so! Chrishell and Jason went public in July, almost a year after she claimed on Selling Sunset that her ex-husband, Justin Hartley, informed her via text message when he filed for divorce. Chrishell and Jason’s romance seemed guaranteed to dominate at least some of Selling Sunset’s fourth season—but now it seems Season 5 will have to document their break-up.

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Speaking with Us Weekly in November, Oppenheim said the pair’s friendship had created a solid foundation for something more. “We had been so open about what we were looking for with each other because we had become close friends. She knew my dating life, and we would almost joke about our each other’s dating lives and what we were looking for and things like that.”

Weeks later, however, sources confirmed to People that after a five-month romance in the public eye, the couple had split. At least this means Selling Sunset Season 5 might have more to offer than the delightfully wicked Christine Quinn.

Kim Kardashian and Pete Davidson

Is this relationship the biggest PR stunt since BenAna took those fashionable pap walks with their dogs? Quite possibly. But is it not also possible that after seemingly one of the most exhausting marriages in celebrity history, Kim Kardashian just wanted to get stoned, ride rollercoasters, and soak in some BDE?

I really could go either way on this one. It is my strong conviction that a lot of celebrity women simply find it refreshing to hang out with a mild-mannered stoner. Then again, would I be surprised to learn that this is all a big conspiracy designed to sell Skims? The happy couple has already staged a pretty compelling product shot in matching PJs, so...

But then again, does it really matter how “real” any of this is? Given the aforementioned reality that none of us will ever know the true nature of a celebrity coupling, if the presentation is good and the narrative is fun, I’m inclined to just go with it.

Rita Ora and Taika Waititi

What’s Rita Ora up to? She’ll be getting engaged imminently, if The Daily Mail is to be believed. The tabloid reported this week that the Kiwi director and his No. 1 are headed to Australia for Christmas, where Ora hopes to receive an engagement ring.

She and Waititi first went public in April, and a month later a photo emerged of the couple canoodling with Tessa Thompson, which turned out to be the perfect image to kick off an extremely bored, pandemic-fried public’s slutty summer. As far as 2021’s surprising celebrity pairings go, this one definitely had shock value.

Speaking about the steamy photos to the Sydney Morning Herald in June, the Jojo Rabbit director insisted his viral moment wasn’t bothering him too much. “I think in the world of the internet, everything goes away pretty quick,” Waititi said. “And also, ‘Is it that big a deal?’ No, not really. I was doing nothing wrong. It’s fine.”

Channing Tatum and Zoë Kravitz

When we first saw photos of these two making flirty appearances in the East Village with a constant rotation of bikes, I declared them the hottest maybe-couple of summer 2021—and I stand by it!

This magical pairing has since confirmed their coupledom. And while they, like others on this list, share a potential commercial reason to stage a relationship—in this case, Kravitz’s directorial debut, Pussy Island, in which the onetime Magic Mike stars as a philanthropist and tech billionaire—I gotta say, I’m totally buying it!

Maybe it’s because they share the kind of chemistry, even just in photos, that makes me want to talk about, like, energy. Or maybe it’s my undying love for a couple that bikes together, especially while looking as mutually hot—which these two seem to do with total ease.

Or maybe I’m still simply charmed by this little bit of banter, shared with Deadline as the two discussed their upcoming joint project. I do love a woman who bullies her man about his choice of footwear—in this case, Crocs. Reminiscing on the time she got Tatum to abandon the look, Kravitz told her co-star, “Just to be clear, there are people out there who can pull off the Crocs thing; I just wasn’t sure you were one of them.”

“She had a good argument,” Tatum conceded. “The one thing I can pull off is listening.”

Hot!

Bennifer: The Sequel

It’s probably glaringly obvious by now that I’m a mark for a good stunt—and as far as stunty couples go, it’s hard to top the one that broke the internet with a single nostalgic butt touch.

Coverage of Jennifer Lopez and Ben Affleck’s relationship was less than charitable when they first hooked up in the mid-aughts, so there’s something poetic about them reigniting things after all these years. There’s also the fact that our path to this reunion involved an extremely complicated love quadrilateral that ultimately sent Ana de Armas and Alex Rodriguez packing. After all the hateful coverage Jen and Ben first endured, which always felt at least a little classist and racist, there’s something thrilling about watching them take an attention-grabbing victory lap by making out in airports and recreating scandalous moments from old music videos.

Ben Affleck Says Backlash Over Jennifer Garner Comments ‘Hurts My Feelings, Man’

I’ll admit, however, that this one was higher on my list until the recent controversy surrounding Affleck’s comments to Howard Stern about his marriage to Jennifer Garner. Affleck has clarified that he was not, in fact, blaming Garner for his struggles with alcohol when he told Stern that he'd “probably still be drinking” if they were still married because he felt “trapped” in the relationship. The actor said his and Stern’s two-hour conversation had been cut down to give an inaccurate impression of his remarks, which could certainly be the case.

Speaking with People, Lopez said the reports about her being frustrated over her beau's comments were “simply untrue.” She added, “I couldn’t have more respect for Ben as a father, a co-parent, and a person.”

“[It] made me out to be the worst, most insensitive, stupid awful guy,” Affleck later said of his interview with Stern. “I would never want my kids to think I would ever say a bad word about their mom.”

Controversy aside, however, I cannot deny that the second coming of Bennifer has been one of my greatest sources of delight for most of this year.

Olivia Wilde and Harry Styles

Can you believe that Olivia Wilde and Harry Styles holding hands at that wedding, in turn shocking a nation, happened this year? Neither can I, but we must weather this surreality together. (And yes, before you ask—they, too, have a project to promote together: Wilde’s Don’t Worry Darling, in which Styles was tapped to replace Shia LaBeouf.)

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WildeStyle had supposedly been a thing for a while by the time we all got a look at those wedding pics back in January, and reports conflicted as to how and when things had ended between Wilde and her ex-husband, Jason Sudeikis. But even in the days before the hookup was officially official, the excitement was palpable. Our very own Kevin Fallon captured the situation perfectly at the time:

“All I know is that things are gross in the world right now and the news cycle, even the celebrity one, has been increasingly unpleasant,” he wrote. “But oh-so-briefly, I saw leaked photos (that probably should never have been taken at a private event, but there they were anyway) of two extremely likable people holding hands at a wedding, and I thought, well that’s nice. That feeling, to me, was newsworthy.”

Since then, the couple have been seen supporting one another at various events, making out on a yacht in Italy, and (possibly, probably) sharing jewelry. It’s always nice to see two people living while they’re young. And as for Sudeikis? Don’t worry, after spending a year as the world’s sexiest mascot for divorced dad energy, he seems to be doing just fine now.

Porsha Williams and Simon Guobadia

Remember that time “Porsha” was trending above “Israel” and “Palestine” on Twitter for more than 24 hours? That’s how you know a celebrity couple’s chaotic union has a vise grip on our collective throats.

Less than a week after Simon Guobadia announced his split from Real Housewives of Atlanta star Falynn, Williams announced her internet-breaking engagement to her co-star’s ex.

Falynn has made clear she does not blame Williams for how her marriage ended. “Simon and I were the ones who were married to one another,” she said in a June interview. “We’re the ones who created a family together and built a life with one another. I blame the both of us. He is to blame, I am to blame, and that is all. Whatever came after that—not saying it was right, not saying it was wrong—but no, no one has that power.” She has since announced her engagement to Jaylan Banks—with whom Guobadia has previously accused her of having an affair. The drama never stops.

Kourtney Kardashian and Travis Barker

Of all the seemingly unorthodox celebri-couples that have captivated the internet this year, it’s hard to think of one with more powerful “Sk8er Boi” energy than Kourtney Kardashian and Travis Barker, whose thumb-sucking amore became borderline inescapable in 2021.

For some, this couple might have already overstayed their welcome. But Barker’s vulnerable disclosures about the relationship have only made their narrative more compelling from this writer’s armchair. Consider, for instance, Barker’s explanation of how Kardashian helped him overcome his trauma from a 2008 plane crash that killed two of his friends.

“It’s still something very new to me, but having something that gives me the strength and hope to be able to overcome things that were so traumatic in my life, it just says a ton,” Barker told Nylon in September. “She’s definitely that for me. I’m invincible when I’m with her. It’s like, I never dreamed, I never even considered flying again.”

By the time the couple announced their engagement in October with photos from the rose-filled beachside proposal, three words seemed to sum up a nation of gossip lovers’ reaction: We’re feeling this.

Andrew W.K. and Kat Dennings

Getting engaged just one month after going public with your relationship? As Andrew W.K. and Kat Dennings might say, “When it’s time to party, we will always party hard.”

I might be biased as someone who attended one too many house parties in college, but pound-for-pound and Instagram post-for-Instagram post, Andrew W.Kat has provided a certain sect of millennial fans a distinct kind of joy.

Compared to some of the (delightfully) exhibitionist couples on this list, Dennings and Mr. Wilkes-Krier have kept things pretty low-key, sharing adorable photos that expertly toe the line between aspirational celebrity relationship and relatable Instagram fodder.

The two announced their engagement in May, and it didn’t take long for some fans to begin asking—based on the rings they wore in some photos—whether they were already married. As much fun as staged stunts and oversharing are, we also simply love a couple that keeps us guessing—especially one with such complementary and enviable manes.

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