Last Updated on July 18, 2025 by Colby Droscher
The Prohibition Era, spanning from 1920 to 1933, wasn’t just about dry laws; it was about rebellion, creativity, and a nation in flux. With alcohol banned across the U.S., underground clubs flourished, bootleggers made fortunes, and ordinary citizens danced through speakeasies with a cocktail in hand and the law on their heels.
These rare, vintage photos capture the energy, contradictions, and hidden glamour of the time. From jazz-fueled gatherings to daring raids and hidden flasks, each snapshot tells a story of defiance and adaptation during one of America’s most paradoxical decades.
1. Ladies Demonstrate the Art of Wine Smuggling with Grace and Grit
2. Smashing Spirits: Government Agents Destroy Liquor Stockpiles in 1920
3. Federal Agents and the New Normal: “No Booze Sold Here” Becomes the Law of the Land
4. A Mountain of Moonshine: Confiscated Barrels Stacked Sky-High
5. Hidden in Plain Sight: Federal Agent Uncovers Booze in a Lumber Truck
6. Busted at the Bar: Boston Speakeasy Raided During Prohibition
7. Smuggling with a Smile: Women Bootleggers Outsmart the Law in 1921
8. Guns, Grit, and Guts: A Moonshiner’s Wild Kentucky Operation in the Early 1900s
9. Side by Side: Bootleggers and the Law Pose for an Unlikely 1928 Snapshot
10. Down the Drain: Agents Dump Liquor into the Streets During Prohibition
11. Marching for Their Pints: Protesters Demand “We Want Beer” in the Streets
12. A Dry Agenda: Prohibition Party Convention Sets the Stage in 1892
13. “Alcohol vs. Prohibition”: A Stark Visual from 1931’s Dry Crusade
14. “I’m Not a Bootlegger”: A 1929 Plea Near the Mexican Border
15. The Birger Gang: Bootleggers, Bandits, and a Slice of Southern Illinois History
16. The Darkest Strategy of Prohibition: When the U.S. Government Poisoned Alcohol, Killing Over 10,000 People
17. Men Share a Barrel of Bootleg Liquor During the Height of Prohibition
18. Flooding the Streets with Booze: Agents Dump Confiscated Liquor in a Public Display of Power
19. The Bootlegging Belles: Fearless Women Who Ran the Rum Trade Like a Business Empire
20. Al Capone, the Face of Prohibition-Era Crime
21. Moonshiners Wore Cow Shoes to Evade Authorities, And Their Booze Trails Left No Prints Behind
22. How Prohibition Turned Walgreens into a Pharmaceutical Empire
23. “Just Add Water”: Grape Brick Labels That Hinted at Homemade Wine
24. The Booze Returns: Americans Rejoice as Prohibition Comes to an End
Explore more historical content:
The Prohibition Era was just one chapter in a century full of change. If you’re fascinated by history told through powerful images, check out our collection of 25 Iconic Moments in History Captured in Color, revisit the final glimpses of greatness in 19 of the Last Known Photos of Famous Historical Figures, or discover the wild stories behind 15 Vintage Inventions That Never Took Off.
