44 Vintage Photos Of Speakeasies, The Underground Bars Of Prohibition-Era America

Published December 7, 2022
Updated December 10, 2022

While Prohibition was in effect in the United States from 1920 to 1933, speakeasies popped up across the nation as places where people could buy alcohol illegally.

Shortly after the end of the first World War and leading up to the Great Depression, two monumentally important periods in American history co-existed: The Roaring ’20s and Prohibition.

It seems strange that an era known for its surging economy, lavish parties, jazz, and the Harlem Renaissance covers the same gap of time as the era in which the production, sale, and transportation of alcohol was almost entirely banned across the United States — until you account for speakeasies.

Men Sharing A Drink
Pussyfoot Is Coming Sign
Dumping Liquor In The Gutter
People Outside Krazy Kat
44 Vintage Photos Of Speakeasies, The Underground Bars Of Prohibition-Era America
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Speakeasies were, in essence, illicit bars and clubs that sold alcohol to their clientele. As the Mob Museum acknowledges, however, these "discreet" spots were Prohibition's worst-kept secrets. By the end of the 1920s, there were more than 32,000 of these "gin joints" in New York alone.

In fact, speakeasies were so prominent that they came to define pre-Depression America more than anything else. Many of the iconic images that the 1920s conjure up — flapper girls, mob bosses like Al Capone, Jazz-Age noir — stem from the culture that speakeasies created.

The Not-So-Secret World Of Prohibition-Era Speakeasies

Naturally, many Americans were upset when the 18th Amendment and the Volstead Act made it illegal to sell alcoholic drinks. This led to a massive and entirely underground business known as bootlegging — the production and sale of illegal alcohol.

The Prohibition movement came about as a result of growing waves of religious revivalism in the 1800s that ushered in calls for temperance and other "perfectionist" ideas like the abolitionist movement to end slavery.

While we can look to the latter as a positive example of this growing ideology, the Prohibitionist movement can largely be considered a historic failure.

Bootleggers Cart Toppled

Buyenlarge/Getty ImagesA wrecked car belonging to bootleggers, who were carted off to prison. 1921.

The push for Prohibition came from a few large sects: the Woman's Christian Temperance Union, the Anti-Saloon League, and factory owners who wanted to reduce workplace accidents and make their employees more productive during their egregiously long shifts.

The rise of evangelical Protestantism also saw saloon culture as corrupt and ungodly, and a large number of women additionally felt that alcohol ruined families and marriages.

Initially, Prohibition was a temporary measure instituted by Woodrow Wilson in order to preserve grain for food production during wartime, per HISTORY. Congress later introduced the 18th Amendment, which was officially ratified on January 16, 1919.

By then, 33 states had already implemented some kind of Prohibition legislation.

But the United States government struggled to actually enforce Prohibition over the course of the nearly 14 years it was in place. At first, the IRS was put in charge of enforcement, but the responsibility was later transferred to the Justice Department and the Bureau of Prohibition.

The "Drys" raided hundreds of illicit bars during the '20s and early '30s, but the overwhelming number of speakeasies that popped up across the country made the task effectively impossible.

Like modern drinking establishments, speakeasies ranged from hole-in-the-wall dive bars with rough seats and a few choices of beer to lavish, extravagant clubs with tableside service. They also offered something that prior drinking establishments hadn't: the chance for men and women to drink together.

In short, people who wanted to drink were still finding ways to do so — which meant there was money in making alcohol, even if it was technically illegal.

And given that alcohol production and operating speakeasies was already an illicit activity, it was the perfect industry for enterprising organized crime bosses to stake their claim and get rich.

How Prohibition Led To A Surge In Organized Crime

There were a couple of factors that allowed speakeasies to thrive during Prohibition, but perhaps the two largest were the massive number of gang members working to transport alcohol and the fact that only 1,500 federal agents were given the job of enforcing the alcohol ban.

That number breaks down to roughly 30 agents per state. Again, there were more than 30,000 speakeasies in New York alone. By some estimates, that number was actually as high as 100,000.

Organized crime gangs immediately seized the opportunity. Within one hour of Prohibition going into effect, six armed men stole $100,000 worth of "medicinal" whiskey from a train in Chicago.

All across the country, gangs were stockpiling booze supplies, but one gangster in particular made his name — and his money — in dealing out illegal alcohol and even lauded himself as a sort of contemporary Robin Hood: Al Capone.

Al Capone

ullstein bild/ullstein bild via Getty ImagesGangster boss Al Capone and his attorney Abraham Teitelbaum in 1931.

"I'm just a businessman," Capone would say, "giving the public what they want."

Of course, the "businessman" was a far cry from the hero he portrayed himself as, as evidenced by the infamous 1929 St. Valentine's Day Massacre in which Capone ordered seven Chicago rivals to be gunned down by his gangsters.

Still, at the height of his activity, Al Capone was raking in tens of millions of dollars every year from his illegal booze business.

In New York, Charles "Lucky" Luciano found similar success when he brought together some of the biggest Italian and Jewish mobsters to control the city's bootlegging industry.

Lucky Luciano

Bettmann/Getty ImagesCharles "Lucky" Luciano drinking wine in New York City.

Arnold Rothstein, the man who fixed the 1919 World Series, profited from importing Canadian booze across the Great Lakes, down the Hudson, and into New York. And in Cleveland, the Mayfield Road Gang made their mark on history by rum-running speedboats across Lake Erie.

Some of these guys, like Meyer Lansky, avoided Capone's fate by wiring money to Swiss brokers to cover their tracks.

By the time Prohibition was repealed in 1933 with the passing of the 21st Amendment, gangs and especially gang leaders had stores of cash that allowed them to continue to live extravagantly well into the Great Depression — and they continued to make a profit thanks to loansharking and other booming criminal activities.

It's little wonder why Winston Churchill, looking at American Prohibition from across the sea, called the law "an affront to the whole history of mankind."

After this look into the notorious speakeasies of the Prohibition era, check out photos that showcase flappers, the "It Girls" of their day. Then, explore the aftermath of Prohibition's repeal — and the spontaneous parties that popped up across America.

Austin Harvey
A staff writer for All That's Interesting, Austin Harvey has also had work published with Discover Magazine, Giddy, and Lucid covering topics on mental health, sexual health, history, and sociology. He holds a Bachelor's degree from Point Park University.
Cara Johnson
A writer and editor based in Charleston, South Carolina and an assistant editor at All That's Interesting, Cara Johnson holds a B.A. in English and Creative Writing from Washington & Lee University and an M.A. in English from College of Charleston and has written for various publications in her six-year career.