Whats a good movie set in the 20s that captures the spirit of New York at the time?

I'm reading The Great Gatsby (required) right now and I want to have a good picture in my head as I do so. I want to avoid watching any of the movies based on it because
1. I don't want any spoilers
2. I hear they're very drear
I have a pretty broad taste in movies so any recommendations are welcome but try to limit it to one.

Can't remember if it is set in New York or not but The Roaring Twenties with Cagney is a pretty good film about the 20's...

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Sergio Leone's Once Upon a Time in America spans a few decades, but the scenes where the characters are young kids are set in 1920s Brooklyn, New York. The film runs at three hours and forty minutes, so it may be a bit long if you just want an idea but it's an excellent film. And the scenes in the 20s happen in the first half of the movie anyway.

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I'm not sure if you want to watch a film not only set in the 1920s but also made in the 1920s, but I've got two. I know you said to limit it to one, but I couldn't choose between Josef von Sternberg's The Docks of New York and King Vidor's The Crowd.

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Gangs of New York has a very good oldschool style. Look for the keyword "bootlegger", since that was very popular during that time - Gatsby is suspected to be one.

Gangs of New York was set in the 1860's, but seeing as you've banned Peehouse, I'm sure you don't care.

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"Don't be so gloomy. After all it's not that awful. Like the fella says, in Italy for 30 years under the Borgias they had warfare, terror, murder, and bloodshed, but they produced Michelangelo, Leonardo da Vinci, and the Renaissance. In Switzerland they had brotherly love - they had 500 years of democracy and peace, and what did that produce? The cuckoo clock."

First of all, does anyone today really know what New York City looked like in 1920-1929? Any movie made from 1930 through today is only guessing what New York looked like in the 1920s.

For instance, there was no Empire State Building back then—excavation for what for a long time would be the world’s tallest building didn’t start until January 22, 1930. Radio City Music Hall didn’t open until 1932. Rockerfeller Center, the largest private building project ever undertaken in modern times, didn’t get underway until 1930.

There was no LaGuardia airport. Fiorello LaGuardia didn’t become mayor of New York until 1934 (through 1945). What was to become LaGuardia Airport started as 105 acre private flying field built in 1929 in Queens on land that was once occupied by Gala Amusement Park. In 1937, ground was broke for a new airport built jointly by the city and the Federal Works Progress Administration. It was named New York Municipal Airport-LaGuardia Field and opened to commercial traffic in 1939.

Can’t go by shots of the Hindenburg over New York—that was in 1937. Can’t tell for sure from movies of the World War victory parade through ticker tape from Wall Street—that happened in 1919.

However, Babe Ruth hit the first home run in the new Yankee Stadium up in the Bronx in 1923. And over in Brooklyn, Ebbets Field opened in 1913 and was home stadium for the Brooklyn Dodgers from 1913-1957. It was demolished in 1960.

The 22-story Flatiron Building on 175 Fifth Avenue was in 1902 one of the first skyscrapers ever built, one of the first to use a steel skeleton, and one of New York’s largest buildings.

From 1918-1929, automobile traffic in New York City increased by more than 500,000 vehicles, but no new highways had been built, causing near gridlock. The Depression brought an end to construction of a West Side Highway, begun in 1927, and the Triborough Bridge, begun in 1929. The Holland Tunnel opened in 1927, but the George Washington Bridge wasn’t finished until 1931. There still was much horse-drawn transportation in New York, and the sanitation department had to remove dead animals and tons of manure from city streets. This, of course, attracted flies and rats that spread disease. There also were many outhouses still in use in sections of the city. Most heating was from coal that polluted the air and deposited soot on all the buildings.

New York City became the most populous urbanized area in the world in early 1920s, with some 6 million residents. City government was still dominated by Tammany Hall, as it had been for the past 70 years. In 1923, New York produced 1/12th of all US manufacturing. America’s ready-made clothing industry was centered in New York, employing many immigrants. The US didn’t begin to restrict foreign immigration until 1924, but Ellis Island became the primary screening center for immigrants in 1892. The nearby Statue of Liberty was erected in 1886.

Some 200,000 African Americans moved to New York in a great migration from the rural South in 1917-1925, attracted to Harlem on the city’s East Side. Jazz was popular, with such Jazz greats as Coleman Hawkins, “Duke” Ellington, “King” Oliver, “Jelly Roll” Morton, Louis Armstrong, and Bessie Smith living in New York.

Jack Johnson, the first black heavyweight boxing champion, opened the Club De Luxe at 142nd Street and Lenox Avenue in Harlem in 1920. Owney Madden, a prominent bootlegger and gangster, took over the club in 1923 while imprisoned in Sing Sing and changed its name to the Cotton Club. While the club was closed briefly in 1925 for selling liquor, it reopened without trouble from the police. Several of the greatest black musicians and dancers performed at the Cotton Club over the years, but blacks generally were not accepted as customers. It closed for good in 1940.

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