In 1977, Frank Sinatra wasn't exactly looking for a comeback, but he definitely needed a change of pace. He was "Old Blue Eyes," the Chairman of the Board, a guy who had spent decades playing the suave romantic or the wisecracking leader of the Rat Pack. Then came Contract on Cherry Street. It wasn't a glitzy musical or a big-budget Hollywood epic. Instead, it was a three-hour television movie—his first and only one—and it was surprisingly mean, gray, and fed up.
Watching it today feels like peering into a specific, gritty pocket of New York City history that doesn't exist anymore.
If you’re looking for the Sinatra who snaps his fingers and winks at the camera, you’re in the wrong place. This movie is about a New York City Police Inspector named Frank Hovannes who is tired of seeing his colleagues murdered while the justice system basically shrugs its shoulders. It’s a precursor to the "angry cop" tropes we see everywhere now, but back then, seeing a star of Sinatra’s magnitude playing someone this disillusioned was a huge deal.
The Reality Behind Contract on Cherry Street
The movie is based on a 1975 novel by William H. Hallahan. It’s important to understand the vibe of New York in the late 70s to get why this resonated. The city was broke. Crime was skyrocketing. People felt like the rules didn't work anymore.
Sinatra’s character, Hovannes, loses his partner to a mob hit. When the official investigation gets bogged down in red tape and legal technicalities, Hovannes decides to go rogue. He assembles a small, elite team of officers to start taking out mobsters outside the law. It’s a "vigilante cop" story, but it plays more like a procedural tragedy than a Death Wish clone.
Honestly, the pacing is a bit of a slow burn. Since it was a TV movie, it had to fill a massive time slot. That means we get a lot of scenes of guys in cheap suits sitting in dimly lit rooms, smoking, and talking about the "way things used to be." But that’s actually the movie’s secret weapon. It feels lived-in. It feels like 1977.
Why Sinatra Took the Role
By the late 70s, Sinatra’s film career had cooled off. He hadn't made a movie in seven years. He chose this project specifically because he liked the book's tough-guy realism. He didn't want to be a caricature; he wanted to show he could handle a heavy, dramatic lead without the tuxedo.
He also brought along some heavy hitters. The cast includes Martin Balsam, Harry Guardino, and Richard Castellano (the guy who played Clemenza in The Godfather). This wasn't some cheap TV production. It was a serious attempt at high-stakes drama.
Breaking Down the Visuals and Atmosphere
The movie was shot on location in New York. You can practically smell the exhaust and the damp pavement. Director William A. Graham didn't try to make the city look pretty. He captured the graffiti-covered subways, the crumbling storefronts, and the oppressive grayness of a winter in the city.
There’s a scene early on where the camera just lingers on the faces of the cops at a funeral. You see the genuine exhaustion. It’s not "Hollywood" sad; it’s "I’ve-done-this-six-times-this-year" sad. That authenticity is what makes Contract on Cherry Street stand out from the polished police procedurals of the era like Kojak or Columbo.
- The Cinematography: It’s grainy. It’s handheld in spots. It feels like a documentary at times.
- The Music: Jerry Goldsmith did the score. If you know film music, you know Goldsmith is a legend. He didn't go for a jazzy, Sinatra-style soundtrack. He went for something tense and driving.
- The Dialogue: It’s full of "cop talk." Lots of jargon, lots of cynical quips, and very little sentimentality.
Where the Movie Stumbles (And Where It Wins)
Let’s be real: at three hours, it’s a marathon. Modern audiences might find the middle hour a bit sluggish. There are subplots involving the internal politics of the mob that feel a bit like they belong in a different movie.
However, the payoff is worth it. When the "contract" actually starts to play out, the tension ratchets up. You start to see the toll vigilante justice takes on Hovannes. He’s not a hero. He’s a guy who is slowly losing his soul because he thinks it’s the only way to save his city.
There is a specific moral ambiguity here. The film doesn't necessarily cheer for Sinatra’s character. It asks if he’s becoming the very thing he’s trying to destroy. In 1977, that was a pretty sophisticated theme for a television audience.
The Supporting Cast is Incredible
Martin Balsam plays Ernie Gantz, and his chemistry with Sinatra is the heart of the film. They feel like two guys who have known each other since the academy. They don't need big speeches to communicate. A look or a shared cigarette says everything.
Richard Castellano brings that same grounded, terrifyingly normal mobster energy he had in The Godfather. He doesn't play a villain; he plays a businessman whose business happens to be murder. It’s that lack of melodrama that makes the violence feel more impactful when it finally happens.
The Legacy of Cherry Street
Why does this movie still matter? Well, for one, it's a time capsule. If you want to see what the Lower East Side actually looked like before it was gentrified into high-end boutiques and $15 lattes, this is your movie.
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But more than that, it’s a masterclass in "Late-Period Sinatra." He’s older, he’s grumpier, and he’s using his natural gravitas to carry a story that could have been very thin in the hands of a lesser actor. He doesn't sing a single note. He doesn't even smile much. It’s a performance of restraint.
Impact on the Police Genre
You can see the DNA of Contract on Cherry Street in later shows like Hill Street Blues or even The Wire. It moved away from the "case of the week" format and focused on the systemic rot and the emotional fatigue of the job. It was gritty before "gritty" was a marketing buzzword.
How to Watch It Today
Finding a high-quality version can be a bit of a hunt. It pops up on retro cable channels or budget DVD sets. Because it was a TV movie, it didn't always get the 4K restoration treatment that Sinatra’s big studio films received.
If you find it, watch it in a dark room with no distractions. Let the atmosphere sink in. Don't expect an action-packed blockbuster. Expect a somber, thoughtful, and occasionally brutal look at a man trying to fix a broken world with broken tools.
Actionable Takeaways for Movie Buffs
If you're planning to dive into this 1970s gem, here is how to get the most out of the experience:
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Check the Runtime
Make sure you’re watching the full version. Some television edits cut it down to two hours, which ruins the pacing and removes the character development that makes the ending work. You want the full 150+ minute experience.
Context is Everything
Before watching, look up some photos of NYC in 1977. Understanding the "Ford to City: Drop Dead" era of New York history will help you empathize with Sinatra's character's frustration.
Compare to The First Deadly Sin
If you enjoy Sinatra in this, watch his final film, The First Deadly Sin (1980). It’s a perfect thematic companion piece—another dark, rainy New York cop drama where he plays an aging man facing a world he no longer recognizes.
Listen to the Score
Pay attention to Jerry Goldsmith’s work here. It’s a great example of how a composer can elevate a "small" TV project into something that feels cinematic.
Watch for the Character Actors
The 70s was the golden age of "that guy" actors. See how many faces you recognize from The Sopranos, The Godfather, or Law & Order. It's a fun game of "who's who" for crime film fans.
Contract on Cherry Street is a reminder that even the biggest stars in the world sometimes need to strip away the glamour to find something real. It’s a tough, unsentimental piece of filmmaking that deserves a spot on the shelf of any serious crime cinema fan.