Honestly, the 1960s were a weird time for gangster movies. Everything was shifting. We were moving away from the "G-Man" hero worship of the thirties and heading toward the gritty, cynical realism that would eventually give us The Godfather. Right in the middle of that transition, a director named Budd Boetticher dropped a movie that most people today have completely forgotten.
It’s called The Rise and Fall of Legs Diamond.
If you’re a film nerd, you probably know Boetticher for his lean, mean Westerns starring Randolph Scott. Those movies are masterpieces of minimalism. But when he stepped into the world of Prohibition-era New York, he brought that same "no-nonsense" energy to the story of Jack Diamond. It’s a movie that feels like it’s vibrating with a specific kind of cold, calculating energy.
Why the movie is basically a psychological study
Most gangster biopics try to make you like the guy. They give him a "heart of gold" or a tragic backstory with a mean mother or a starving childhood in the slums. This movie? It doesn't care about your feelings.
Jack "Legs" Diamond, played by Ray Danton, is a total sociopath.
Ray Danton is fascinating here. He’s got this debonair, matinee-idol look—sharp suits, perfect hair—but his eyes are like two chips of ice. Boetticher actually famously hated Danton. He once said Danton was one of the few actors he truly despised. But weirdly, that tension works for the film. Diamond isn't a hero. He’s a guy who uses everyone—his sickly brother Eddie (played by a young Warren Oates), his wife Alice, his mistresses. Everyone is just a stepping stone.
The "Bulletproof" Myth
One of the coolest parts of The Rise and Fall of Legs Diamond movie is how it handles the real-life legend that Diamond was "bulletproof." In history, the guy was shot so many times he was nicknamed the "clay pigeon of the underworld."
In the film, this becomes his fatal flaw: hubris.
After surviving a hit, Diamond starts to actually believe the hype. He thinks he’s invincible. There’s a scene where he basically tells the National Crime Syndicate—the big bosses like Lucky Luciano (referred to in the movie as "The Chairman" because Luciano was still alive in 1960 and they didn't want a lawsuit)—that they have to pay him.
It’s bold. It’s also incredibly stupid.
What's real and what's Hollywood?
Look, let’s be real: 1960s Hollywood wasn't exactly obsessed with historical accuracy. They "cleaned it up," as Boetticher put it.
- The Arnold Rothstein Connection: In the movie, Diamond rises by becoming the bodyguard for Arnold Rothstein. This is actually true to life. Diamond was a Rothstein protégé before the "Big Bankroll" got rubbed out in 1928.
- The Europe Trip: There’s a weird sequence where Diamond goes to Europe on vacation. In reality, he went to Europe (specifically Germany) to try and score a massive narcotics deal. The movie portrays it more as a getaway where he realizes the world has moved on without him.
- The Brother: Warren Oates plays Eddie Diamond, Jack’s brother. In the movie, Jack basically abandons him when his sickness becomes a liability. The real Eddie was indeed a close associate, but the movie cranks the "cold-hearted" dial up to eleven to show how ruthless Jack was.
Boetticher wanted to make a movie about a "miserable son-of-a-bitch" who you’d admire for two seconds because he was so damn good at being bad, and then immediately feel gross about it. He succeeded.
The Cinematography of Lucien Ballard
You can't talk about The Rise and Fall of Legs Diamond movie without mentioning the look of it. Lucien Ballard shot this thing in gorgeous, high-contrast black and white.
It doesn't look like a standard 1960s flick.
It looks like noir on steroids. The shadows are deep. The jewelry stores and nightclubs gleam with a fake, predatory kind of light. It moves fast, too. Boetticher was working with a 24-day shooting schedule, which is insane for a feature film. That pressure forced him to cut the fat. The movie is a "narrative juggernaut." It rushes from one double-cross to the next without pausing for breath.
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Why it still matters today
You might wonder why anyone should care about a sixty-year-old gangster movie.
Well, it’s basically the bridge to the modern anti-hero. Without Ray Danton’s "chilly" performance, you might not get the detached cool of some of the great 70s crime leads. It also features the film debut of Dyan Cannon (credited as Diane Cannon), playing a flashy little tramp named Dixie. Seeing her and Warren Oates before they became icons is a treat for any cinema buff.
Also, it’s one of the few movies that captures the "fall" of the old-school freelance gangster.
When Diamond returns from Europe, he finds that crime has become a "business." It’s organized. It’s a syndicate. A guy like Diamond—a loud, flashy, independent operator—doesn't fit in the new corporate world of the Mafia. He’s an dinosaur. Watching him struggle to realize his era is over is actually kinda sad, even if he is a jerk.
The Failed Musical?
Fun fact: They actually tried to turn this movie into a Broadway musical in the late 80s. Peter Allen starred in it. It was... a disaster. It closed after only 64 performances. The musical tried to make Legs Diamond a likable, song-and-dance hero. The critics hated it. They realized what Boetticher knew in 1960: Jack Diamond only works when he’s the guy you love to hate.
Actionable Next Steps for Film Fans
If you're looking to actually watch or study this era of crime cinema, don't just stop at the big names. Here is how to dive deeper:
- Track down the Warner Archive release: The DVD and digital transfers of this film are surprisingly crisp. The black-and-white cinematography by Ballard really needs a high-quality screen to appreciate the "chiaroscuro" lighting.
- Watch it as a "Double Feature": Pair it with Budd Boetticher’s The Tall T or Ride Lonesome. Seeing how he applies the same "masculine code" and tight pacing to both a Western and a Gangster film is a masterclass in auteur directing.
- Read "O Albany" by William Kennedy: If you want the real dirt on Jack Diamond's death, this book is the gold standard. It explores the theory that the Albany police—not the mob—were the ones who finally put the "clay pigeon" down for good.
- Compare the "Gangster Cycle": Watch this alongside the 1959 Al Capone (starring Rod Steiger). You’ll see how 1960 was the year Hollywood finally stopped making gangsters look like cartoon villains and started making them look like dangerous, modern men.