6 Best Speakeasy and Prohibition Bootlegging Movies

By Vlad Zakh · April 6, 2026

Drama intensethought provoking

The illicit glamour of the Prohibition-era speakeasy has fueled some of cinema’s most enduring gangster dramas and comedies.

Lawless (2012) 01

Lawless (2012)

IMDb ★ 7.1

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

Public Enemies (2009) 02

Public Enemies (2009)

IMDb ★ 7.0

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

Road to Perdition (2002) 03

Road to Perdition (2002)

IMDb ★ 7.6

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

The St. Valentine's Day Massacre (1967) 04

The St. Valentine's Day Massacre (1967)

IMDb ★ 6.6

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

Some Like It Hot (1959) 05

Some Like It Hot (1959)

IMDb ★ 8.2

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

The Roaring Twenties (1939) 06

The Roaring Twenties (1939)

IMDb ★ 7.7

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

Vlad Zakh

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.