The real Great Gatsby in Westport

Casey Manzella
Features Editor

While it has generally been assumed that F. Scott Fitzgerald’s iconic American novel, The Great Gatsby was influenced solely by Great Neck, Long Island, history teacher Richard Webb has unearthed another possible influence in the making of his new documentary. “The Great Gatsby has often been linked with Great Neck, Long Island as being its setting and its influences,” he said. “What we’re arguing is, while it is not necessarily untrue, the town of Westport, Connecticut has a very large role in that too.”

Having grown up in Westport, Mr. Webb has long held an interest for all things Fitzgerald. “I grew up about half a mile away from the house the Fitzgeralds lived in during the 1920s so I was literally a neighbor of the Fitzgeralds, just 75 years later,” he said. “I was very familiar with, and interested in, Scott and Zelda from the time I was 14 onwards.”

Since his childhood, Mr. Webb’s passion for the Fitzgeralds has only grown through the making of his documentary. “Mr. Webb is devoting incredible amounts of time and energy to this project and he has been for years now,” history department head Robert Stevenson said. “It’s exciting to see him moving in some awesome directions with it.”

As Mr. Webb has continued to explore the roots of The Great Gatsby he has developed an even greater appreciation for Westport and its history. “All of a sudden you realize, wow, history was made here,” he said. “Real stuff happened here that was of importance. You feel part of a bigger thing; part of a bigger trend. It’s very cool and breath-taking actually. It’s like you walk into a really cool, old house that has secrets.”

The secrets Mr. Webb has discovered in Westport have convinced him of the legitimacy of his thesis. “Well, facts are stubborn things,” he said. “Once you see the facts the rest takes care of itself. You just have to know where to look.”

Many of these facts come from the Fitzgeralds’ honeymoon Westport in 1920. “They’re young,” Mr. Webb said. “They are the first rock stars in American history. They get married in New York and move to Westport, Connecticut for a five month honeymoon. It is such a fast-paced time of heavy partying and wild partying and hookups and romances and car accidents and cops being called and fire departments being called. It’s a very romantic time.”

The Fitzgeralds spent their honeymoon in a small rental house on 244 Compo Road South, which Mr.

Scott and Zelda Fitzgerald spent their honeymoon in this Westport house in 1920. Mr. Webb believes the house is the inspiration for Nick Carraway's house.
Photo by Casey Manzella
Scott and Zelda Fitzgerald spent their honeymoon in this Westport house in 1920. Mr. Webb believes the house is the inspiration for Nick Carraway’s house.

Webb believes is the inspiration for Nick Carraway’s house in The Great Gatsby. Next to this house is the Longshore Country Club, which was formerly the house of millionaire Frederick E. Lewis. Known for his frequent, extravagant parties that so openly displayed his opulence, Lewis is featured as the inspiration for Jay Gatsby in the documentary.

In addition to these tangible pieces of evidence, many find thematic connections between The Great Gatsby and Westport. “There’s friction among the classes in The Great Gatsby,” English department head Heidi D’Acosta said. “I think the haves and have-nots live in very close proximity in Fairfield County. Connecticut has one of the widest gaps in wealth in the country because we live near New York where there are very high-paying jobs. That is definitely reflected in the book.”

While there are a multitude of similarities between life in the 1920s Westport and The Great Gatsby, some believe Westport was only a minor influence on the novel. “I’m sure that every place he went influenced his writing of The Great Gatsby,” English teacher Robert Darken said. “He’s just writing about American people.”

Mr. Stevenson feels similarly. “Fitzgerald is writing fiction and the best fiction probably comes from actual experiences, but those experiences are an amalgam of your life experiences,” he said. “The collection of his life experiences, more than any single place, time or event, probably inspired The Great Gatsby.”

Although Mr. Webb feels Westport is a major influence, he also feels other areas of the United States could be too. “There’s a great quote by Scott Fitzgerald: ‘None of my characters are not Scott Fitzgerald. All of my characters are Scott Fitzgerald,’” he said. “All he wrote about was his personal experience. All his characters were him and in The Great Gatsby he’s bringing to bear all of his experiences, and Westport is one of them.”

While there may not be one single place that influenced The Great Gatsby, Mr. Webb has enjoyed finding proof of Westport’s influence. “As I explored this thesis I began to realize that doing a documentary was a really fun thing,” he said.

Although they may be fun to produce, good documentaries require a lot of work. “A good documentary is about the people who are making it as much as the content they are making it about,” Mr. Webb said. “My documentary is about obsession. I’m so old and I’ve been pursuing this for so long.”

Money is also necessary to bring a documentary to fruition. “You need a lot of money,” Mr. Webb said. “You do this through a series of campaigns called kick-starters and you go on community appeals. We have raised $25,000 to date and we will need, and will get, another $25,000 over some time.”

While that money is used for the obvious costs such as film equipment, there are also many hidden costs. “The large amount of the money goes toward copyright because we’re going to be using two segments from two different Great Gatsby movies,” Mr. Webb said. “We have to pay for the scene shots from that. We also have to pay the Fitzgerald family and the Princeton library for all the photos we’re using. You have to pay for every single photo you use for copyright law.”

While Mr. Webb’s documentary will not be complete until the end of the year, some are not excited to see the influence of The Great Gatsby possibly determined. “I’m not excited to see it settled,” Mr. Stevenson said. “History is more interesting when there are multiple theories and ideas about it. Mr. Webb making the case is the thing that makes it interesting more than whether or not it is truth. The exciting part is that someone working with this material almost 100 years later is still seeing new things in it and finding new connections and meanings.”

Mr. Webb also has greater aspirations for his documentary than to just reveal Westport as the inspiration for The Great Gatsby. “When this idea came out we were told it was not even possible,” he said. “Historians told us this, teachers told us this, everyone told us this. The main thing is that you can never assume that something is true just because you’ve been told so. What I hope this becomes is an instructive lesson in if you really want to figure out the facts, you better check them yourself. Just because you’re told something is true, doesn’t mean it is.”