6 Best Speakeasy and Prohibition Bootlegging Movies

By Vlad Zakh · April 6, 2026

The illicit glamour of the Prohibition-era speakeasy has fueled some of cinema’s most enduring gangster dramas and comedies. In Some Like It Hot (1959): Two musicians disguise themselves as women to escape mobsters after witnessing a bootlegging massacre. Don’t overlook The Roaring Twenties (1939): A war veteran’s rise and fall in the bootlegging trade unfolds across the Prohibition era.

Lawless (2012)

TMDB ★ 7.1

Three bootlegging brothers in rural Virginia defy a corrupt deputy determined to shut down their operation.

Directed by John Hillcoat · 1h 55m · Rated R

Where to watch

Stream: fuboTV, Lionsgate+ Amazon Channel · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube

▶ Trailer Letterboxd

Public Enemies (2009)

IMDb ★ 6.9 RT 68% Metacritic 70

FBI agents pursue the notorious bank robber John Dillinger across a Prohibition-era crime spree.

Directed by Michael Mann · 2h 20m · Rated R

1 win & 14 nominations

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Road to Perdition (2002)

TMDB ★ 7.6

A mob enforcer and his son go on the run after witnessing a brutal betrayal within the organization.

Directed by Sam Mendes · 1h 57m · Rated R

Where to watch

Rent: JustWatch TV, Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

The St. Valentine's Day Massacre (1967)

TMDB ★ 6.6

Rival Chicago bootlegging gangs escalate their war toward a notorious real-life massacre.

Directed by Roger Corman · 1h 40m · Rated NR

Where to watch

Stream: History Vault · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Some Like It Hot (1959)

IMDb ★ 8.2 RT 95% Metacritic 98

Two musicians disguise themselves as women to escape mobsters after witnessing a bootlegging massacre.

Directed by Billy Wilder · 2h 03m

Won 1 Oscar11 wins & 13 nominations

Where to watch

Stream: fuboTV, MGM+ Amazon Channel, Philo, MGM Plus Roku Premium Channel, YouTube TV, MGM Plus · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

The Roaring Twenties (1939)

TMDB ★ 7.7

A war veteran's rise and fall in the bootlegging trade unfolds across the Prohibition era.

Directed by Raoul Walsh · 1h 44m

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Streaming availability data from JustWatch, via TMDB. Availability changes often, so check the service before you plan a movie night.

Vlad Zakh

Founder, Movieix

Founder of Movieix, built to fix a specific annoyance: most recommendation sites are just algorithm-driven noise. Our lists are researched and organized by who's in a film, where it's from, and the mood you're actually in tonight.

6 Best Speakeasy and Prohibition Bootlegging Movies

Lawless (2012)

Public Enemies (2009)

Road to Perdition (2002)

The St. Valentine's Day Massacre (1967)

Some Like It Hot (1959)

The Roaring Twenties (1939)

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