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A Photographic Tour of Times Square in the 1920s

The 1920s, known as the Jazz Age, was a period of unprecedented prosperity and social energy in America, and nowhere was this more visible than in Times Square. The district reached its peak as a global entertainment hub, defined by its spectacular theaters, illicit nightlife, and immense, bustling crowds.

The Golden Age of Broadway

The theater industry experienced its most productive decade in history. During the 1927 season alone, more than 250 shows opened on Broadway. The era was defined by lavish musical comedies and groundbreaking productions. In 1927, the musical “Show Boat” opened at the Ziegfeld Theatre, changing American theater with its serious storyline that integrated songs into the plot.

Alongside live theater, magnificent new movie palaces opened, attracting thousands of patrons. The Capitol Theatre and the Roxy Theatre, which opened in 1927, were two of the largest and most ornate. These were not simple cinemas; they offered a full evening’s entertainment that included a live orchestra, singers, dancers, and a feature film for a single ticket price.

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Prohibition and Hidden Nightlife

The nationwide ban on alcohol, known as Prohibition, did little to slow down the party in Times Square. The law simply pushed the vibrant nightlife scene behind closed doors. The side streets surrounding Broadway were filled with hundreds of speakeasies—hidden bars and nightclubs that illegally sold alcohol.

These establishments were often run by notorious gangsters like Owney Madden and Larry Fay. Inside, patrons could drink cocktails, listen to live jazz bands, and dance the Charleston. The constant threat of police raids added a sense of danger and excitement to the atmosphere. This underground scene made Times Square the glamorous, illicit heart of New York City after dark.

Crowds, Cars, and Congestion

The popularization of the automobile transformed the physical landscape of Times Square in the 1920s. For the first time, the streets became choked with traffic, as cars, taxis, and buses competed for space with the still-present streetcars. The sidewalks were constantly packed with a dense mix of New Yorkers and tourists flocking to the area’s attractions.

To manage the chaotic flow of people and vehicles, the city installed its first automated traffic signals in the district. The constant movement, the roar of engines, and the sheer density of the crowds became a defining feature of the Times Square experience.

The End of an Era

The decade of nonstop celebration came to a sudden and dramatic end. On October 29, 1929, the U.S. stock market crashed, triggering the start of the Great Depression. In the days following the crash, anxious crowds gathered in Times Square, staring up at the electric news zipper on the Times Tower as it reported the grim financial news. The boundless optimism of the Roaring Twenties had vanished.

#1 The Theatre district around Times Square, New York, 1920s.

The Theatre District Around Times Square, New York, 1920S.

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#2 The Theatre district around Times Square, New York, looking south, showing the Times Building in the center, 1920s.

The Theatre District Around Times Square, New York, Looking South, Showing The Times Building In The Center, 1920S.

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#3 The Theatre district around Times Square, New York, viewed from the Times Building, showing Long Acre Square in the distance and the Hotel Claridge in the foreground, 1920s.

The Theatre District Around Times Square, New York, Viewed From The Times Building, Showing Long Acre Square In The Distance And The Hotel Claridge In The Foreground, 1920S.

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#4 The Theatre district around Times Square, New York, showing large crowds leaving the theaters, 1920s.

The Theatre District Around Times Square, New York, Showing Large Crowds Leaving The Theaters, 1920S.

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#5 The Theatre district around Times Square, New York, seen from Broadway, 1920s.

The Theatre District Around Times Square, New York, Seen From Broadway, 1920S.

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#6 General view of Times Square public garden, with the Paramount Building to the right and the former Times high rise, 1920.

General View Of Times Square Public Garden, With The Paramount Building To The Right And The Former Times High Rise, 1920.

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#9 News stand for out-of-town newspapers in Times Square.

News Stand For Out-Of-Town Newspapers In Times Square.

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#10 Crowd gathers in Times Square for the 1921 World Series.

Crowd Gathers In Times Square For The 1921 World Series.

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#12 The Paramount Building under construction in New York City, mid-1920s.

The Paramount Building Under Construction In New York City, Mid-1920S.

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#13 Traffic and illuminated advertisements in Times Square at night, seen from 45th Street looking northward, 1921.

Traffic And Illuminated Advertisements In Times Square At Night, Seen From 45Th Street Looking Northward, 1921.

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#15 Raymond Hitchcock rides the Masonic goat in front of the public library in New York to draw attention to the Fashion Bazaar and Beauty show, 1920s.

Raymond Hitchcock Rides The Masonic Goat In Front Of The Public Library In New York To Draw Attention To The Fashion Bazaar And Beauty Show, 1920S.

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#16 Raymond Hitchcock rides the Masonic goat in front of the public library in New York, 1920s.

Raymond Hitchcock Rides The Masonic Goat In Front Of The Public Library In New York, 1920S.

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#17 Aerial view of Times Square, New York, early 1922.

Aerial View Of Times Square, New York, Early 1922.

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#18 Boxy back taxi accommodating men in tall silk hats, with the Hotel Astor on the left and Claridge on the right, Times Square, 1920s.

Boxy Back Taxi Accommodating Men In Tall Silk Hats, With The Hotel Astor On The Left And Claridge On The Right, Times Square, 1920S.

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#19 Times Square winter scene with cars in snow, a Horn & Hardart automat, and theater marquees, 1920s.

Times Square Winter Scene With Cars In Snow, A Horn &Amp;Amp; Hardart Automat, And Theater Marquees, 1920S.

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#20 A crowd gathers in Times Square to watch the account of the Jack Dempsey and Tommy Gibbons fight, 1923.

A Crowd Gathers In Times Square To Watch The Account Of The Jack Dempsey And Tommy Gibbons Fight, 1923.

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#21 Streetcars are part of the traffic in Times Square, 1920s.

Streetcars Are Part Of The Traffic In Times Square, 1920S.

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#22 A car with wings and a propeller drives through Times Square, New York.

A Car With Wings And A Propeller Drives Through Times Square, New York.

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#23 Times Square looking north from 45th Street with pedestrians, automobile traffic, and advertising signs, 1920s.

Times Square Looking North From 45Th Street With Pedestrians, Automobile Traffic, And Advertising Signs, 1920S.

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#24 View of marquees for the Plymouth, Laurette Taylor, the Music Box, the Imperial, and the Klaw Theaters along 45th Street at night, Times Square, 1925.

View Of Marquees For The Plymouth, Laurette Taylor, The Music Box, The Imperial, And The Klaw Theaters Along 45Th Street At Night, Times Square, 1925.

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#25 A time-lapsed photograph of a night scene in Leicester Square, London, 1925.

A Time-Lapsed Photograph Of A Night Scene In Leicester Square, London, 1925.

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#26 Broadway on a Rainy Night, Times Square, New York, New York, 1920s.

Broadway On A Rainy Night, Times Square, New York, New York, 1920S.

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#28 Times Square, looking north from 44th Street, New York, New York, 1925.

Times Square, Looking North From 44Th Street, New York, New York, 1925.

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#29 Automobiles and a streetcar pass illuminated theater marquees and billboards at night in Times Square, 1926.

Automobiles And A Streetcar Pass Illuminated Theater Marquees And Billboards At Night In Times Square, 1926.

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#31 Steel workers perched on a steel beam during their lunch break during the construction of the Paramount Building on Broadway in Times Square.

Steel Workers Perched On A Steel Beam During Their Lunch Break During The Construction Of The Paramount Building On Broadway In Times Square.

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#33 Two cars leaped from the subway rails of Times Square station, causing a fatal accident, August 1927.

Two Cars Leaped From The Subway Rails Of Times Square Station, Causing A Fatal Accident, August 1927.

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#34 A large crowd waits outside the Warners’ Theatre to see the premiere of The Jazz Singer.

A Large Crowd Waits Outside The Warners' Theatre To See The Premiere Of The Jazz Singer.

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#35 Steamroller breaks up a Communist meeting in Union Square by paving the street where the meeting was held.

Steamroller Breaks Up A Communist Meeting In Union Square By Paving The Street Where The Meeting Was Held.

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#36 Times Square, looking south from 47th Street, with the Palace Theatre on the left, 1929.

Times Square, Looking South From 47Th Street, With The Palace Theatre On The Left, 1929.

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#38 Traffic Policeman, Duffy Square, Broadway and Seventh Avenue, 1929.

Traffic Policeman, Duffy Square, Broadway And Seventh Avenue, 1929.

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#39 Nighttime view of traffic and neon-illuminated theater and cinema signs in Times Square, 1920s or 1930s.

Nighttime View Of Traffic And Neon-Illuminated Theater And Cinema Signs In Times Square, 1920S Or 1930S.

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Written by Dennis Saul

Content creator and Professional photographer who still uses Vintage film roll cameras. Not that I loved London less But that i Love New York City More.

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