From speakeasies tucked behind unmarked entrances to intrepid bootleggers with contraband liquor, the Prohibition era was a time of rebellion — and ingenuity. Risky as it was, one thing was clear: The nationwide ban on alcohol was not going to stop Americans from drinking. Instead, it drove the party underground, fueling a shadow economy where jazz, cocktails, and crime thrived side-by-side.
These vintage photos of Prohibition capture an era that changed how people socialized — and how far they were willing to go for a sip of booze.
1. Hey, Who You Calling a Booze Hound?
2. Men Enjoying One Last Drink Before the Start of Prohibition, 1920
3. A Police Officer Inspects a ‘Lumber’ Truck After Smelling Alcohol Coming From It, Los Angeles, 1926
4. A Speakeasy in Boston Gets Raided By Undercover Cops, 1920
5. NYPD Deputy Commissioner John Leach Watches as Barrels of Illegal Booze Get Poured Down the Sewer, 1921
6. A Clever Man Finds a Loophole To Get His Hands on Some Wine
7. A Female Rum-Runner Showing Her Secret Stash, 1920
8. A July 4th Parade Float Against Prohibition Urging the Public to ‘Use a Little Wine for Thy Stomach’s Sake,’ 1921
9. Women From the Temperance Movement Delivering a Bold Message, 1919
10. Americans in Paris Celebrate the End of Prohibition, 1933
11. ‘A Bar in New York City the Night Prohibition Ended, December 1933’
12. Protesters Take to the Streets With Pretty Clear Demands, 1931
13. Chug, Chug, Chug: Flappers Disregarding Prohibition Laws, 1925
14. ‘Prohibition-Era Bootleggers in St. Paul, Minnesota, 1921’
15. A Flapper Serves Drinks to a Crowd of Men After Prohibition Ends
16. ‘Ladies Having a Drink at a Speakeasy Bar During Prohibition, 1920s’
17. ‘Fedora-Wearing FBI Agents Escort Prohibition-Era Gangster, George ‘Machine Gun’ Kelly, to Court in Memphis, Tennessee, 1933′
18. Prohibition-Era Bootleggers Secretly Making Booze, 1930
19. ‘First Beer Delivery in Ohio After Prohibition Is Repealed, 1933’
20. Julius Stroh of the Stroh Brewing Company Celebrates His Company’s First Legal Pour of Beer, May 1933
21. Worst Hangover Ever: ‘The Morning After Prohibition Ended, 1933’
22. Patrons Bidding Farewell to the 18th Amendment, December, 1933. Just Look at the Size of Those Goblets!
23. A Flapper Reveals Her Hidden Flask, a Clever Way Women Smuggled Booze During The Prohibition Era
24. Partygoers Mock the 18th Amendment as They Toast With Bottles Hidden in Plain Sight, 1920s
Wondering what else was going on in the ’20s?
Go back in time with 20 Dreamy Photos That Show Why Paris in the 1920s Was Pure Magic and 35 Photos That Show the Wild Energy of the 1920s. And don’t miss These 9 Vintage Ads From the Roaring ’20s Show How Much Prices Have Changed.
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