Upper East Side in Fiction
upper east side

The Upper East Side has always been one of the most affluent and prestigious neighborhoods in New York. With its exclusivity, beautiful architecture and fascinating residents, it has always been a popular setting for authors. Here are our favorite moments for the Upper East Side in literature.

The Great Gatsby, F. Scott Fitzgerald
The classic novel masterfully captures the booming Long Island of the 1920s, but its wealthy socialite characters are no strangers to Manhattan either. Some of the key action in the plot, in fact, takes place at the landmark Plaza Hotel at 768 Fifth Avenue — it’s the site of the raging argument between Tom Buchanan and Jay Gatsby over both Gatsby’s relationship with Daisy and his shady dealings. And it makes perfect sense that the characters would spend time in a place of such opulence.

Breakfast at Tiffany’s, Truman Capote
Truman Capote once described Holly Golightly as an “American Geisha.” It makes perfect sense she would live on East 71st St, on the Upper East Side, surrounded by Manhattan’s wealthiest bachelors. Capote mixed real venues with fictional ones throughout the novella, but he kept much of the action on the UES. Holly buys a tapestry in the very real Park Bernet Galleries on 980 Madison Avenue and is no stranger to Fifth Avenue. Hamburger Heaven (at 79th and Madison) and Joe Bell’s Bar (Lexington in the East 70s) were both haunts for the book’s characters as well.

The Bonfire of the Vanities, Tom Wolfe
Like American Psycho, Tom Wolfe’s hugely popular novel uses the Upper East Side to capture the spiraling wealth there in the 1980s. Bonfire travels all over New York, as a means to juxtapose the richest and the poorest residents of the city and separate them, neighborhood by neighborhood. Sherman McCoy lives on the Upper East Side and he works on Wall Street – a rich kid, getting ever richer. His life is presented here in stark contrast to the poverty-stricken people of Harlem and the Bronx.

Catcher in the Rye, JD Salinger
Salinger was no stranger to the Upper East Side, having lived at 1133 Park Avenue and 300 East 57th St (which was his final Manhattan address), so it’s no surprise that the parents of Catcher’s anti-hero Holden Caulfield live there too. After his expulsion from the Pencey Prep boarding school, Holden wanders all across Manhattan, on his journey home. One gets the feeling that his disillusionment with materialism and “phonies” has to do with his privileged background, and, one could argue, that his wandering of the city is a means to put off returning to the Upper East Side for as long as possible.

Image courtesy of: Nicholas Wang