#664: The Roaring Twenties

1939 gangster classic takes a look at one of America’s craziest decades

june gloom
4 min readMar 18, 2025

Initial release: October 23, 1939
Director: Raoul Walsh

America has always spent a lot of time looking back. The 1980s has enjoyed a revival of reputation in the last fifteen years that simply wasn’t possible in the 1990s; that decade, meanwhile, is coming back into style too. As soon as the 1970s ended people were nostalgic for it; the 1950s, too, lingers long in the national memory, though moreso if you were white (and ideally straight.) And by the end of the Dirty Thirties, nostalgia for those halcyon days of the Roaring Twenties was at an all-time high. And why not? War was around the corner, the Great Depression had bottomed out a once-thriving economy, and fascism seemed to be everywhere.

(Hm. I feel like we’ve seen this episode before.)

Raoul Walsh is a guy whose name keeps popping up in mid-century film — gangster flicks, film noirs, westerns, even a few war movies. In a very real sense, he is Old Hollywood, with his eyepatch and a filmography of 160 movies (on both sides of the camera!) across half a century. Some of the biggest, best, or just plain most important movies of the era have his name on them: White Heat, The Big Trail (starring a nearly fetal John Wayne in his first lead role, and also the earliest surviving widescreen flick,) the landmark proto-noir They Drive by Night, and of course — The Roaring Twenties, two parts gangster film, one part 1920s retrospective, and joining together none other than Humphrey Bogart and James Cagney.

The Roaring Twenties isn’t just a period piece, it’s a deliberate look back at the decade from the precipice of war, explicitly described as such by a newsreel-style narrator, who periodically returns to fill in the audience with incredible time-skip montages. While the film’s title is somewhat deceptive — it starts in 1918 and ends maybe just after Prohibition is repealed in late 1934 — the core of it is of course that heady decade of the 1920s, an era where Prohibition not only did nothing to stop the flow of alcohol but empowered organized crime, resulting in an epidemic of ever-increasing gang violence, the dark undercurrent to the dancing and singing and provocative fashion and the rise of Golden Age Hollywood and all the other glitz and glitter of that incredible epoch. Into this heady mix is Eddie Bartlett (Cagney), George Hally (Bogart), and Lloyd Hart (Jeffrey Lynn, fresh off his famous role in Four Daughters), three veterans of World War I who met by accident in a foxhole. Following the war, they each go into a career: Lloyd begins his law practice, George becomes a merchant ship captain, and Eddie, short of options, goes into the taxi business… which soon becomes a front for bootlegging. Oh, Eddie doesn’t touch the stuff himself, no — but he’s more than happy to sell it to nightclub hostess Panama Smith. As Eddie’s wealth grows and the market gets more crowded with tough guys looking to make cheap cash in the booze biz, he happens to run into George, who’s been running booze himself for a rival mob boss. He talks George into switching sides, but it soon becomes clear that George is a bit unhinged. As the decade nears its final, crashing end, Eddie loses everything: all his money, lost on the stock market; his bootlegging empire, succumbing to economic and legal pressures and forcing him to sell his cab company to a spiteful, vengeful George; and the love of his life, who never really loved him back.

The Roaring Twenties is a lot of things at once, but Walsh keeps the plates spinning with incredible cinematography — some of the montage sequences that mark the passage of time must be seen to be believed for their sheer audacity by 1930s standards. Cagney is in fine form as he grows from naive ex-soldier to street-smart gangster to his final form as a run-down wreck. Bogart, in one of his most sinister roles this side of Fred Dobbs, plays a great psychopath in George, a bloodthirsty snake who resents other people having power over him. It’s not just a tale of a gangster’s rise and fall; it’s a tale of the decade, of everything that went into it, good and bad. From our position here watching the world descend into authoritarianism once again, The Roaring Twenties stands as a stark reminder that nothing lasts forever.

Except the 1980s.

-june❤

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june gloom
june gloom

Written by june gloom

Media critic, retired streamer, furry. I love you.

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