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5 Books like the Great Gatsby: From Both Sides of the Paper

Jane Howarth itcherFill your bookshelf with five essential books like The Great Gatsby. If you’re anything like me, you get a little bit curious about the people behind the pen, so I’ve collected a few novels that share Gatsby’s themes and a couple of historical fiction pieces to introduce you to the author.
~ Jane Howarth

What Makes ‘Gatsby’ Your ‘Gatsby’?

‘The Great Gatsby’ earned a glowing review, so I know we’ve got plenty of F. Scott Fitzgerald fans around here. But I also know that there are a lot of reasons why people are drawn to the story, from the captivating but flawed characters with their impossible situations to the glamour of their New York.

I’ve picked out three classic novels, also from the 20th Century, and two fictional histories set in Fitzgerald’s time, which will sweep you up in a world of extravagance and impossibility.

‘Brideshead Revisited’ (Evelyn Waugh, 1945)

In a plot that shares a couple of similarities with Gatsby, the upper middle class narrator of ‘Brideshead Revisited’ becomes enchanted by the decadent Sebastian Flyte and his family while studying at Oxford. We watch as he relives his experiences after the end of the era, seeing both their glories and their paths of destruction.

Waugh was inspired by his own wartime experiences and the end of the Bright Young Things he had previously written about. I think it shows, as we watch these glittering party kids change due to circumstances that can’t be avoided and others of their own doing.

Similarity Match: 90%
We’re in a different social circle, but you’ll recognise a few character types and situations as we watch a decadent lifestyle fade away forever.

‘Breakfast at Tiffany’s’ (Truman Capote, 1958)

What is it about glamorous but unreachable New Yorkers? There’s no doubt that ‘The Great Gatsby’ is a book that loves the Empire State, so let’s skip forwards and see how up and coming socialites are living a few years later.

The distant but magnetic Holly Golightly catches the eye of the narrator, who moves into the same apartment block when he arrives in New York City. But it’s not easy to strike up a relationship with a girl whose dates usually pay for the time they spend together.

Similarity Match: 80%
Obsession, New York, the irresistible pull of magnetic but tragic personalities – sound familiar? Fast forward a few decades and ‘Breakfast at Tiffany’s’ is your updated story of a newcomer in the city.

‘The Two Faces of January’ (Patricia Highsmith, 1964)

This one’s a thriller, which shouldn’t really fit the Gatsby profile, but in some ways it feels surprisingly similar. If you’re looking for another tale of obsession and conflicting indicators of social ranking, read on.

A twenty-something drop-out lives on his wits in Greece, spending his inheritance money and getting by with his flawless language skills. He’s about to meet an American conman and his wife who are determined to life a life of luxury while on the run from authorities. It’s all going to plan, until the conman accidentally kills an agent sent to question them, binding these strange characters together.

Similarity Match: 70%
It’s definitely a thriller, but like ‘The Great Gatsby’ it sets us on some kind of inevitable path to destruction, and you can’t miss the undercurrent of obsession.


If You Like The Great Gatsby You Will Like…

Part of the fascination is the author, whose name you’d know even if you’d never so much as touched the cover of one of his books.

You may or may not like my following picks, because fictionalised accounts of historical events aren’t for everyone. I can only read them if I make a special mental category of things that are slightly factual, slightly not – but that’s good enough for me.

Two authors are about to take us back to the early 20th Century, where we’ll meet a few of the people from Fitzgerald’s circles.

‘The Paris Wife’ (Paula McLain, 2011)

Paula McLain imagines life from the perspective of Hemingway’s wife as she gets to grips with life at the heart of the Paris literary scene. Among the real life figures we meet along the way are Zelda and Scott Fitzgerald, sending us into one influential phase in all the authors’ lives.

The writing echoes the rhythm of the ‘Great American Novel’ as you’d find it in Hemingway or Fitzgerald’s work, setting a pace that the reader can’t meddle with. And this is probably an unintended consequence, but with the main players coming from a similar society, you’ll spot similar character traits to the ‘Gatsby’ line-up.

It’s meant to focus on Hemingway from his wife’s perspective, but ‘The Paris Wife’ absorbs so much of American literary society you’ll feel like you’re entering ‘Gatsby’ and Fitzgerald’s world.

‘Gatsby’s Girl’ (Caroline Preston, 2013)

Caroline Preston profiles F. Scott Fitzgerald’s first love and sometime muse. We meet the author as a teen who falls for the slightly younger Ginevra, and the author takes us on an imagined turn as we watch Ginevra uncovering the similarities between herself and characters like Daisy Buchanan.

Not so much mimicking the pace of the narrative as the pace of Fitzgerald’s life, ‘Gatsby’s Girl’ will make you take another look at Daisy – yep, it’ll also inspire a re-read of ‘Gatsby’.


It Looks Like You Can’t Have Glamour without the Decay

We just can’t move for cocktails and destruction in here today, but would you like an introduction to a captivating fictional character, or a real one? Personally, I go through phases of each, so I’ll pick one from each side of the desk and go for ‘Gatsby’s Girl’ and ‘Brideshead Revisited’.

Know exactly which books similar to ‘The Great Gatsby’ you’d add to the list?

Let us in on your favourites in the comments.

Hi, I’m Jane, BA (Drama, Film and TV) and MA (Cultural and Creative Industries). When I’m not writing about creative things, I’m designing or planning them. If you’re brave enough to risk an avalanche, look behind the stacks of books and DVDs and you’ll find me balancing a cup of tea, a handful of knitting and a cupcake.
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