31 Photos From Prohibition That Capture Its Wild History

Prohibition, spanning from 1920 to 1933, was one of the most tumultuous and bizarre chapters in American history. It was an era defined by secret speakeasies, daring bootleggers, and federal agents waging war on alcohol.

These 31 photos capture the chaos, creativity, and contradictions of a time when the U.S. tried—and failed—to ban booze. From wild underground parties to elaborate smuggling operations, these images offer a fascinating glimpse into a bygone era that thankfully remains in the past.

Buckle up for a trip through the Roaring Twenties and beyond, when people found ingenious (and sometimes absurd) ways to keep the party alive.

1. Two American soldiers at a bar in Seattle on December 3rd, 1919, just 45 days before Prohibition started.

Two men in uniform stand at a bar with drinks in hand. A bartender stands behind the bar. A sign reads, "There are just 45 drinking days left." American flags decorate the bar, and several people are in the background.

I love the “There are just 45 drinking days left” sign.

2. Patrons make one last run to a liquor store in Chicago before Prohibition starts on January 15, 1920.

Black and white photo of a crowded 1920s bar. Men and women in period attire, including hats and suits, gather around the bar counter filled with bottles. The lively scene suggests a bustling atmosphere typical of the Prohibition era. — NordyNed

The guy on the left’s face says it all.

3. Having one last drink on the last day before prohibition started in 1920.

A group of men, dressed in vintage attire with hats, gather around a barrel labeled "Roll out the Barrel." Most are drinking from mugs. The setting appears to be an outdoor area with a wooden structure in the background. — HelloSlowly

Bottoms up, fellas. It’ll be 13 years before you can do that legally again.

4. Bar during Prohibition on Waterloo Avenue in Cleveland, Ohio, in 1920.

Two men in hats lean over a dark wooden bar in a dimly lit room, appearing to have a conversation. The bar is equipped with taps and there are bowls to the left. The room has a vintage, early 20th-century ambiance. — MyIpodStillWorks

Seems to me that you really wouldn’t want to have ended up in one of these pictures.

4. A federal agent inspects a ‘lumber’ truck after smelling alcohol during Prohibition in Los Angeles in 1926.

Two men unload bricks of grass from the back of a vintage delivery truck. A large rectangular opening is visible in the stacked grass bricks. Another person is partially visible underneath the truck. A building with signs is in the background. — tacchassen

Pretty creative way to try to conceal it. It clearly didn’t work. But still creative.

4. Anti-Prohibition protesters

A black-and-white photo shows a group of men in coats and hats marching on a street at night, holding signs that read "We Want Beer." A large crowd is gathered along the sides, watching the march. — Jneebs

Labor Union members in Newark, New Jersey.

5. Prohibition-era bootleggers in St. Paul, Minnesota (circa 1921).

Two women wearing work overalls and caps stand in front of shelves lined with industrial tools and equipment. One holds a long cylindrical object, while the other rests her hand on her hip. Both wear dust-covered clothes and smile at the camera. — liamlars

I would watch a 10-part HBO miniseries on these two.

8. Group of women defiantly breaking Prohibition laws in 1925.

Four women in vintage clothing stand against a wooden wall, each drinking from dark bottles. They wear hats and dresses, with one in polka dots, enjoying a sunny day. The scene has a nostalgic, early 20th-century feel. — youngvein

As playfully brazen as this may seem, I can’t help but notice those bottles are empty.

9. California prohibition agents confiscating a fuel tank with 250 bottles of tequila hidden in it circa 1930.

Four men stand behind a table filled with bottles labeled “Corno-malt syrup.” They examine the bottles and a metal contraption resembling a still. A framed picture hangs on the wall behind them. Black and white image. — FPG/Staff/Getty

The bottles were being smuggled into the U.S. from Mexico. The man on the far left and far right were arrested with the contraband.

10. A woman is arrested for serving alcohol illegally from her “bootlegger’s life preserver” in 1924.

1920s woman in a dress and fur coat concealing metal containers under her arms, likely as a form of smuggling during Prohibition. The image is in black and white, capturing the fashion and clandestine activity of the era. — ExploreMoreMysteries

I would love to know how much one of those things carries.

11. Cops pouring alcohol into the sewers at Van Brunt St. and Sackett St. in Brooklyn.

Historical photo of men pouring alcohol into a sewer during Prohibition. Two men handle the barrel while others, including a uniformed officer, look on. A vintage wagon and brick building are visible in the background. — Buyenlarge/Contributor

The nonuniformed man watching is New York City Deputy Police Commissioner John A Leach, who famously was guilty of indulging at least once during Prohibition.

12. Kids catching runoff from poured out booze.

Children playing and gathering water from a gutter on a cobblestone street. Some are seated on the sidewalk with buckets and containers, while others stand or gather in groups. The background shows more children and a few adults near buildings.

It’s a well-documented (and disgusting) fact that kids would often rush to catch as much poured-out booze from a bust as they could so that they could sell it back to adults.

13. Cow shoes that moonshiners used during Prohibition to disguise their footprints.

Black-and-white photo showing two views of a novelty shoe with hooves. The top image displays the shoe alone, while the bottom image shows a person wearing it. The shoe mimics animal hooves, attached to a regular dress shoe. — yearlyfiscal

Truly brilliant move to hide your tracks.

14. Some rebellious folks during prohibition in the early 1920s.

A group of people in a 1920s-style setting hold and look at a sign stating "In compliance with the 18th amendment, no intoxicating liquor allowed on the premises," while smiling and holding bottles of alcohol around a table. — iamstephen

I didn’t notice at first, but they’re all lighting the corners of this sign.

15. Buying Kosher wine for ‘Sacramental Purposes’ in the 1930s.

A man in a suit and hat walks on a sidewalk carrying two bottles. Behind him, a shop window displays numerous jugs under a banner reading "Kosher Wine for Sacramental Purposes.

You see, Officer. These bottles are for religious ceremonies.

16. Women marching in 1933 calling for the end of Prohibition.

Black and white photo of a 1933 protest. A group of people marches, holding signs that read, "WE WANT BEER." The crowd mostly wears dark clothing, and several American flags are visible. — HawkeyeTen

Every movement needs a simple, catchy slogan.

17. Anheuser-Busch company car selling ice cream to stay afloat.

A vintage black-and-white photo depicting a man at an ice cream truck with "Anheuser-Busch Ice Cream" and pricing details on its side. A man in a shirt and cap serves two young boys in the background. Vintage cars are parked nearby. — Sketchitout

Not sure I’m buying that the words ice cream shouldn’t be in quotes.

18. A haul of prohibited alcohol after a raid on speakeasy bars in New York in 1923.

A black and white photo shows several men in early 20th-century attire standing around open crates and boxes filled with bottles of alcohol. The scene appears to be from the Prohibition era, with boxes stacked against a brick wall in the background. — Dhorlin

I can’t tell if that guy in the center is holding a gun or a bottle, but he looks like he’s about to test the cameraman.

19. Crowd gathering around confiscated and smashed still equipment in Chicago, early 1920s.

A historical black and white photo showing a large group of adults and children gathered in front of a building. They are surrounded by barrels, coiled tubing, and containers, possibly related to distillation or brewing equipment. — Chicago History Museum/Contributor/Getty

Not a smile on the bunch.

20. Contraband beer being poured into the streets from barrels during Prohibition.

A group of men in hats stand along the sides of a street watching a stream of liquid flow from a large barrel. Some hold bicycles. The scene appears to be from an early 20th-century urban setting. — Hulton Archive/Stringer

The restraint of every person in this photo not to just reach down and grab a scoop.

21. Two men pouring alcohol down the drain during prohibition circa 1920.

Two men in white shirts and hats pour bottles of alcohol into a street drain during Prohibition. They stand on a sidewalk with vintage cars and trees in the background. — Hulton Archive/Stringer

It’s pretty telling that every person pouring out hooch in these photos seems miserable.

22. U.S. Federal Agents pouring out wine in Los Angeles on October 26, 1920.

A historical black-and-white photo showing a crowd of people watching as a worker empties a barrel of liquid, likely alcohol, from a cart onto the street. The scene suggests prohibition-era confiscation or disposal. — Bettmann/Contributor/Getty

Apparently, U.S. Federal Agents dumped out a total of 900 gallons that day.

23. Woman at a soda fountain pouring alcohol from her hollow cane in 1922 during Prohibition.

Vintage photo of a woman sitting at a small café table, wearing a coat and hat. She holds a spoon and appears to be stirring her drink. Behind her is a large painting of a Coca-Cola advertisement with two people. — Bucks_trickland

As they say, “Necessity is the mother of invention.”

24. Farewell 18th amendment

A group of people raise glasses in a bar, celebrating. A sign behind the bartender reads "Farewell 18th Amendment." Bottles line the shelf, and the crowd appears joyful. The image is colored, capturing a historic moment of celebration.

Look at the size of that chalice on the left!

25. The night prohibition ended on December 5th, 1933.

A crowded bar scene from the Prohibition era, with men and women in 1920s attire, holding up drinks and smiling. A bartender stands at the bar, arms raised in celebration. The setting is lively and jubilant. — floudbc05

The happiest night that no one remembers.

26. Later that night, when prohibition ended in 1933.

A man in a coat and hat lies asleep on the ground next to a pile of empty alcohol bottles and cartons. The scene appears to be outside, at night. — FinnBiscuit181

In his defense, he does look pretty comfortable.

27. Really celebrating the end of Prohibition.

A group of men in suits and hats are gathered around a piano, drinking from bottles, mugs, and a barrel. One man plays the piano while others enthusiastically pour drinks. The setting appears lively and jovial.

Needless to say, the end of prohibition was enjoyed.

28. “Beer, we have it.”

A vintage black-and-white photo showing men standing on a truck loaded with crates of beer bottles. The truck has a sign reading, "BEER - We have it," followed by a phone number. Other people stand nearby, with one man seemingly drinking.

That guy in the bottom right looks like he needed one.

29. Huge crowds welcoming the return of beer in Los Angeles on April 7, 1933.

A large crowd of people wearing hats and coats line up outside Belmont Grill under a sign that reads "The Most of the Best for Less." Old-fashioned cars are parked on the street. The scene is black and white, suggesting a historical setting. — HsJuggernaut

31. Popular radio performer Jack Pearl Toasting the End of Prohibition.

A man in a uniform enthusiastically raises a mug while standing on barrels with a sign reading "GOOD OLD DAYS ARE BACK AGAIN!" Two men in suits watch. There's a Michel beer poster and wooden crates around them, suggesting a celebration or event. — Bettmann/Contributor

To celebrate the return of the good old days, Jack Pearl and Cliff Hall performed in front of the Michel Brewery in Brooklyn.

Tags: prohibition U.S. History

31 Photos From Prohibition (1920-1933) That Perfectly Capture the Chaos of the Time