From Succession to hit book Pineapple Street: stories of the super-rich

“I’m 43, on the edge of Generation X and Millennial, and my attitude has always been: money seems cool, I would really like to have some! Literally that unexamined,” Jackson admits with breezy candour. “Yet if you were in your 20s right now and had a trust fund, you would probably have complicated feelings about it. So I wanted to write about generational wealth, from generational perspectives.”  

Jackson’s inspiration was also quite literally on her doorstep: living on Pineapple Street in Brooklyn Heights – albeit in a modest flat – she would snoop on more moneyed neighbours. “I was always walking past this apartment with these giant bay windows and a grand piano and those big Chinese urns – like, who lives there?”

In fact, Jackson was well-placed to imagine: while she may hail from middle-class, small-town Massachusetts, when she moved to New York she was thrust into a world of publishing parties and fancy lunches, as well as sharing an apartment with three investment bankers. These days, she gets insights into her neighbours via her children’s pre-school: they recently held a fundraiser where one of the prizes was a child-sized Tesla. Let’s just say, she’s been keeping notes.  

And this, surely, is a key part of the appeal of stories about the mega-rich: the joy of snooping. Whether we aspire to – or are repulsed by – extreme wealth, many of us can’t resist a good gawp at its excesses – or its studiously understated “quiet luxury”.  

Rich-people narratives

At its most basic, the attraction of rich-people narratives can be the opportunity for pure, vacuous fantasy – the escapism of imagining what it would be like to be stinking rich. There’s a reason many romance novels and steamy bonkbusters feature stupidly affluent heroes: why not dream about being swept into the lap of not only a lover, but also luxury?   

But there’s also something particularly tantalising about glimpsing into an elite world that is full of mysterious codes or strict hierarchies. Much of Pineapple Street is spent watching an outsider figure, Sasha, marrying into the family and experiencing “class shame” for getting things wrong. Jackson has a theory about why we’re interested in etiquette: “I think we secretly believe we will one day be millionaires and so we should probably learn the codes so we’re ready. It is a crazy idea, deeply-baked in part of our psyche.”  

Readers have long relished the chance to get an inside scoop on high society’s rules and ruthlessness, the machinations of who’s in or out, up or down. Social standing becomes a game (one that we might just secretly reckon we could win, if we only had the chance). An appetite for such drama is stoked everywhere from reality shows like Real Housewives or Below Deck to Jane Austen and Edith Wharton, Downton Abbey,  Bridgerton and Queen Charlotte.