Why Can’t Billionaires Throw a Good Party?

By Evelyn O’Brien

Two months after Taylor Swift and Travis Kelce’s “wedding of the century,” new details are still making their way into the celebrity press. But beyond the vows, famous guests, and faux castle, the spectacle raises a more enduring question: Why are the parties of the ultrawealthy so often profoundly boring?

notably not a photo from Taylor’s “wedding” … we’d rather be here, though

While Taylor Swift's PR agents slowly drip feed the public details about the "wedding of the century" that was really anything but, now is a great time to remember what we should have learned last summer at the Bezos' wedding. That is, billionaires are losers that wouldn't know how to throw a good party if their lives depended on it. Whatever you think of the wedding industry, it's not hard to conceptualize that if you have wealth beyond what us laypeople will ever see in their lifetimes, if you're going through the effort of putting on a wedding, it will probably be a lavish banquet the likes of which have not been seen since Biblical times. We are hounded with media that holds up the wedding as the most special and important day of a couple's life, one that carries the expectations of immense beauty and a healthy sum of dollars no matter your class. So to see once again that a billionaire is trying to follow these societal expectations by falling so flat on their face would be comical if it wasn't so depressing.

This reflects something wider that most people seem to be realizing as we plod through the Gilded Age 2.0 — billionaires aren't god's special boys and girls. They're just losers who failed upwards for long enough until enough money fell into their laps that made them feel less bad for being such losers. When you've found yourself landing in a Scrooge McDuck pile of currency, whatever shortcomings you may have are suddenly smoothed over by the fact that you can throw money at things and make people like you no matter how vile you truly are.

I don't use the term loser lightly. Many of us who feel like losers really are not. Millennials and Gen Z especially are feeling the bloodcurdling crush of society's expectations while not being able to reach them because of more hurdles than can reasonably listed (fascism! the economy! student loan debt! all of the talking points!!!), and feeling like you're a loser is kind of a multigenerational ennui potpourri. But we can't truly be losers when the systems that we are navigating are set up so that we lose over and over again.

Now, when you're a billionaire, the 1%, gained all there is to gain and then some, and you can't even use those funds to throw a good party, let alone help the world you've exploited for that wealth? That's peak loserdom.

Last summer Jeff Bezos (the Amazon ghoul, for the blissfully unfamiliar) married Lauren Sánchez, and they walked down a carpet that would not look out of place in a windowless office. Or perhaps bus upholstery from the 70s. They walked down this sad blue carpet in Venice, a city they rented out. A city they rented out. And sure, the bride's outfits were subjectively beautiful (tackiness is a matter of taste, after all, so I admit that it is my personal opinion that most of her wedding outfits were quite lovely,) there is nevertheless still some little reminders of loserdom that went down that carpet. For instance, Sánchez claimed that her custom Dolce & Gabbana dress was inspired by Blue Origin, the private space tech company that her husband founded and owns and put her on a vehicle of in 2025. There's nothing like spending your wedding ceremony thinking about the space company your husband-to-be owns, I guess.

They had the entire city of Venice to roam around in — although probably not in the fairytale manner they may have liked, considering that Venice locals protested the wedding — and yet from the outside looking in, everything seemed so hollow. The photo of Bezos and Sánchez that was plastered all over the tabloid websites shows them smiling and looking away from one another, Bezos' mouth opened in an awkward halfhearted grin. There's that goddamn blue carpet and some trees and smiling guests. They could be anywhere in the world. I repeat — why go through the trouble of renting an entire city when all your public photos make it look as though you were anywhere in the world?

There's a reason for this, of course. Those of us in reality recognize the sheer audacity, the absolute ridiculousness of someone renting out Madison Square Garden for a party, surrounded by barriers, or, I repeat, renting an entire city just for your wedding. But despite these mind-boggling details, most billionaires (and one trillionaire, now) want to keep quiet about their money. Elon Musk played a coy little character for years, becoming something of an Internet icon for his sheepishness and fanaticism of online culture — you know, before the poor little rich boy mask came off. Taylor Swift still tries to make herself seem small and meek, spinning a narrative of how everyone betrays her and she's really just the brokenhearted girl next door even now that she's one of the richest women on the planet. Mark Zuckerberg tried to refashion himself as a cool guy who's hip with what people want by trying and failing to start up the Metaverse. There's a kind of veneer of coolness that billionaires conceive of and then fail spectacularly at executing time and time again. Even the nerdiest person you know is cooler than these billionaires, because the nerdiest person you know gives a shit about something and has a passion. Billionaires reach stratospheric wealth and become so desperate to be relatable, to be seen as culturally relevant, to ask that we don't look behind the curtain at their wealth and instead focus on whatever persona they try to project to the public, but they can achieve none of those things.

Obviously, I don't know who was the brainchild behind much of Swift's wedding. I don't care about her nor her verbally abusive husband generally. But I do care about how this kind of ostentatious flaunting of wealth in a time where 37% of Americans can't afford a $400 emergency in cash, for a party that most guests left looking like they'd been at a funeral — is pretty sad. I'm reminded of the Met Gala, where although most people rightfully point out that this kind of display of wealth is unwarranted in our current economic climate, at least we get some usually good fashion, or a fun cultural touchstone to rip on for a few weeks to distract us from the burning world. There is nothing that has come out about the Swift-Kelce wedding that has made me feel a sense of beauty and awe. I have seen a hollow castle inside a large arena and am left wondering how one of the (apparently) biggest stars in the United States couldn't throw a cool wedding.

It's all so bland and infuriating. The barriers outside MSG that only a handful of people leaned against in the sweltering heat dome the Northeast is currently in (which Swift and many others of her billionaire ilk have contributed to in so many ways, not least being private jet use) suggest that Swift's team thought that the Swifties would be rabidly trying to break into the wedding, when no such mob happened. A faux castle as she marries her prince charming who apparently doesn't always wash his feet. 20-minute vows each. The everyday person has smaller infractions at their weddings that are ripped to shreds by family members and online strangers alike.

If Swift had worn orange and indigo camouflage and skydived into the arena from a helicopter at least there would have been something fun or interesting to talk about and laugh at. But instead I just feel sadness and disgust. It's not necessarily that billionaires should justify their existence — they shouldn't exist at all in the first place. And they certainly shouldn't be aspirational even as they try and fail to show off all the things their money can buy. Indeed, it's affirming as a billionaire-despiser that their money cannot buy taste. It cannot even buy a good party where us peons can laugh at how silly it is to spend money on stupidly rare alcohol and designer clothing that leaves us cackling for weeks. Billionaires are failing at being mockable, their one and only public service. Which means we can eat them now.

You can read another essay by Evelyn O’Brien here.