Why We Can’t Stop Watching the Wealthy Fall Apart
They have the money, the wardrobe, the legacy admissions — all served on a silver, inconsequential platter — and still, they’re crumbling.
May’s book of the month, To Have and Have More, taps into the all-consuming world of the privileged at Derrymore Academy. It confronts the uncomfortable truth: you cannot raise a rich, elitist teen who ends up kind. You pick one — and most people pick the money.
So, why are we still so obsessed with the Blair Waldorf archetype? These characters are the worst, and yet… we can’t stop giving them our undivided attention.
The Trope
We know them. From books, from screens, and from real life. The local “rich-kid-with-zero-consequences” — usually (almost always) white, private school educated, magnetic in that glossy, empty kind of way. They’re untouchable. They’re hollow. And somehow, they’re always the main character.
We watch them teeter toward a meltdown, because their money and recklessness are often buffering a darker core: generational pressure, emotional neglect, or the unbearable burden of having everything laid out for you (tragic!).
And even though we’re waiting to see if they evolve, we already know the answer. The arc, if it comes at all, is minor. But the spectacle is the point.
We Hate Them. Are We Them?
There’s a strange duality at play here — one that borders on disgust and obsession. We think we’re better than these characters. We struggle, we read poetry, we shop at secondhand stores and believe that builds character.
They hide their hollowness behind family money. They act on their worst impulses and somehow still land on top.
But maybe that's what keeps us watching — because these are the rules we wouldn’t dare break.
The Hall of Fame: Elite Characters We Love to Hate
Blair Waldorf, Gossip Girl: The meaner she gets, the more we cheer. She schemes. She manipulates. She marries a billionaire who is even more diabolical.
Logan Huntzberger, Gilmore Girls: Rory’s ultimate rich-boy detour. Entitled, charming, reckless (ie: never forget the The Life and Death Brigade stunt in Costa Rica ) — and rarely told “no.” Justice for Marty. (IYKYK)
Kathryn Merteuil, Cruel Intentions: Sex, lies, coke, and couture. The original evil debutante.
The Roy kids, Succession: Pure chaos in Tom Ford. They’re so tragic it’s almost Shakespearean.
As a wise Janis Ian once said, “It’s not my fault you’re like, in love with me or something.”
Fantasy Meets Familiar
These characters captivate us because they straddle the line between fantasy and familiarity. Their environment not only condones but rewards their recklessness. The rules don’t apply. The scandals don’t stick. And the damage? Untraceable.
So what is it that hooks us?
Is it the resentment — for the access, the power, the permanent get-out-of-jail-free card?
Or is it envy — of their chaotic, fearless energy and ability to walk away unscathed?
Ironically, for characters who are so defined by what they own, they seem almost indifferent to it. Luxury becomes a uniform. When you grow up with abundance, you stop noticing the excess.
But let’s be honest — we’re not exactly immune to it either. We pin designer bags to our vision boards every January. We follow their stories for a taste of the world they get to live in daily.
Reflections from To Have and Have More
By the final chapters of To Have and Have More, I found myself (begrudgingly) feeling empathy for Emery. Sure, her parents’ money could buy her out of nearly every scandal and into any Ivy League school — but the racially charged remarks she endures at Derrymore cut deeper- there is no amount of money that can hide the innate racism of her classmates and their families.
Lily’s contrast makes this even sharper. Her financial status never changes, but she’s worked the system at Derrymore, climbed the social ladder, and made herself visible. She isn’t just surviving — she’s excelling, even in a space that isn’t built for her.
Are we satisfied with lacking the wealth in numbers and assets as long as we are giving off the illusion of wealth? Even when the rich fall apart, they have the resources to stitch things back together before it unravels completely. So while they crash and burn, it’s often with a safety net — one that means they never have to really reckon with who they are.
And maybe that’s the real difference. Struggle forces character development. Scarcity builds identity. If suffering “gives you character,” then perhaps wealth strips it away.
Emery is sharp. She’s driven. But can we define who she is beyond the GPA and the scandals? If we tried to build a mood board of her favorite music, movies, humor, style — would it even exist? Or is she just playing the part she was handed?
We hate these characters, but we crave their chaos. They reflect our curiosity, our envy, our worst impulses. And while they may have everything, they often feel like nothing at all.