6 Best Speakeasy and Prohibition Bootlegging Movies

By Vlad Zakh · April 6, 2026

The illicit glamor of Prohibition-era speakeasies fuelled some enduring gangster dramas and comedies. Lawless has bootlegging brothers defying a corrupt deputy, Public Enemies has FBI agents pursuing John Dillinger, and Road to Perdition has a mob enforcer and his son on the run. The St. Valentine’s Day Massacre, Some Like It Hot and The Roaring Twenties round out the six.

Lawless (2012)

TMDB ★ 7.1

Three bootlegging brothers in Prohibition-era Virginia defy a corrupt deputy determined to shut them down.

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

John Dillinger's bank-robbing spree makes him a folk hero the FBI is determined to end.

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 organisation.

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 the mob after witnessing a gangland killing.

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. He started the site because most recommendation pages felt like noise. Here, lists are sorted by who's in the film, where it's from and what mood you're 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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