From Succession to the Bestselling Book Pineapple Street: Stories of the Super-Wealthy

by The Insights

“I’m 43, borderline Gen X and Gen Y, and my attitude has always been: money is cool, I really wish I had it! Literally that without an exam,” admits Jackson with flippant frankness. “Still, if you were in your twenties right now and had a trust fund, you’d probably have complicated feelings about it. So I wanted to write about generational wealth, from a generational.”

Jackson’s inspiration was also literally on her doorstep: Living on Pineapple Street in Brooklyn Heights — albeit in a modest apartment — she spied on wealthier neighbors. “I was always walking past this apartment with these giant picture windows and a grand piano and these big Chinese urns — like, who lives there?”

In fact, Jackson was in a good position to imagine: despite being a middle-class, small-town Massachusetts native, when she moved to New York, she was thrust into a world of publishing parties. and fine lunches, as well as sharing an apartment. with three investment bankers. These days, she finds out about her neighbors through her children’s preschool: they recently held a fundraiser where one of the prizes was a kid’s Tesla. Let’s say she took notes.

And that, surely, is a key part of the appeal of stories about the mega-rich: the joy of spying. Whether we long for – or are repelled by – extreme wealth, many of us can’t resist a good look at its excesses – or its carefully understated “quiet luxury”.

tales of the rich

At its core, the pull of rich stories can be an opportunity for pure, empty fantasy – the escape of imagining what it would be like to be rich. There’s a reason so many steamy romance novels and bonkbusters feature stupidly rich heroes: why not dream of being swept away not only by a lover, but also by luxury?

But there is also something notably trying to glimpse an elite world full of mysterious codes or strict hierarchies. Much of Pineapple Street is devoted to watching an alien figure, Sasha, marry into the family and experience “class shame” for doing things wrong. Jackson has a theory on why we care about the label: “I think we secretly believe that we’ll be millionaires one day and so we should probably learn the codes to be ready. It’s a crazy idea, deeply embedded in part of our psyche.”

Readers have long relished the chance to get a glimpse into the rules and cruelty of high society, the machinations of who’s inside or outside, up or down. Social position becomes a game (a game we might secretly believe we could win, if only we had the chance). An appetite for such drama is stoked everywhere, from reality shows like Real Housewives or Under Deck to Jane Austen and Edith Wharton, Downton Abbey, Bridgerton and Queen Charlotte.

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