Pineapple Street by Jenny Jackson

Honestly, it was the cover of Jenny Jackson’s debut novel Pineapple Street that captured me initially. It had a Great Gatsby feel and, from the first couple of pages, I could tell it was a very character-driven story. The characters weren’t ones I expected though. In fact, they were kind of annoying. Why did you keep reading? Well, the characters were so laughable, so totally not-relatable (except to maybe the wealthiest of New York City), that my reading journey felt like an escapist funhouse. I couldn’t put the book down.

In Pineapple Street, we are introduced to a very Gatsby-esque family: the Stockton family, of old money. We’re immediately given their horrendously selfish personalities, their dysfunction, and the cringe-worthy lives they lead. We meet sisters Darley (the eldest) and Georgiana (the baby of the family), both of whom Jackson propels through their ridiculously rich and privileged social circles. As I said, the immersion into these characters’ lives was semi-annoying, however, I found it laugh-out-loud entertaining. We also meet brother Cord (yes, that is his real name) and his wife Sasha, who married into the family. Sasha could be interpreted as our “realist” voice of the story. We can relate to her confused thoughts, how she truly feels the Stockton family’s culture and values are utterly insane. Yet, we feel her desire to be accepted “within the inner circle” of this family through Jackson’s careful craft. She loathes the Stocktons, yet desires to be accepted by their brash and WASP-like bond.

This story is rich with meaning between words. At surface level, it’s a simple story about a pretentious and advantageous family. Because let’s be honest, not much actually happens plot-wise. But between the lines, Jackson gives us prose full of sharp humor and an escapist feel. Pineapple Street isn’t my favorite book of 2023, but if you’re into “shake your head/what did I just read” laughter, I’d give it a whirl.

Reviewed by Carrie Pung
Hoyt Library