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It’s kind of wild how certain movies just stick in the back of your brain because of the faces you see on screen. When you look at the Once Upon a Time in Brooklyn cast, you aren't just looking at a list of actors; you’re looking at a specific era of New York grit captured on film. Released back in 2013 (though it sometimes feels like a lifetime ago), this movie—originally titled The Last Gamble—brought together a group of people who basically define the "tough guy" aesthetic of East Coast cinema.
Some people came for the mob tropes. Others came because they saw a name like William DeMeo or Armand Assante on the poster and knew exactly what kind of ride they were in for. It's a story about Bobby, a guy fresh out of prison who tries to go straight but gets sucked right back into the life by his own family. It’s a classic setup. But the reason we still talk about the Once Upon a Time in Brooklyn cast is because of how these actors grounded a familiar story in something that felt, well, actually like Brooklyn.
The Man at the Center: William DeMeo as Bobby
William DeMeo didn't just play the lead; he was the engine behind this whole thing. If you’ve watched anything set in the five boroughs over the last twenty years, you’ve seen him. He’s got that authentic energy that you just can't fake in a suburban acting class. In this film, he plays Bobby, a character caught between the crushing weight of his father’s expectations and his own desire to move past a criminal record.
DeMeo has always been a bit of a staple in this genre. Think back to his roles in Analyze That or his later work in Gravesend. He’s got this way of playing "conflicted" without saying much. In Once Upon a Time in Brooklyn, his performance is about the eyes. You can see the exhaustion. He’s a guy who wants out but realizes the exit door is locked from the outside. Honestly, his chemistry with the veteran actors in the room is what keeps the movie from feeling like just another low-budget indie. He holds his own against giants.
The Legends: Armand Assante and Ice-T
Let’s talk about Armand Assante for a second. The man is a powerhouse. When you add someone of his caliber to the Once Upon a Time in Brooklyn cast, the gravity of the scenes shifts immediately. Assante plays Joseph, and he brings that Shakespearean-level intensity he’s known for. Remember him in Gotti? Or American Gangster? He doesn't just deliver lines; he commands the space. In this film, his presence represents the old guard, the traditions that are slowly suffocating the younger generation.
Then you’ve got Ice-T.
Most people know him as Fin from Law & Order: SVU, but his roots in gritty urban drama go way back to New Jack City. In this flick, he plays T-Box. It’s not a massive, sprawling role, but it’s an essential one. Ice-T brings a different flavor of street authority to the screen. While Assante represents the Italian-American mob tradition, Ice-T’s character reminds the audience that the criminal landscape in Brooklyn is a multi-headed beast. His inclusion was a smart move—it broadened the scope of the film and gave it a bit more "street cred" outside of the usual Mafia movie circles.
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The Supporting Players Who Made It Real
A movie like this lives or dies on its ensemble. If the guys in the background don't look like they’ve actually walked down 18th Avenue, the illusion breaks.
- Vincent Pastore: You know him as "Big Pussy" Bonpensiero from The Sopranos. Seeing him here feels like a warm, slightly dangerous hug for fans of mob cinema. He plays Luigi, and as usual, he’s fantastic at being both intimidating and weirdly likable.
- Ja Rule: Yeah, the "Always on Time" rapper. People often forget he had a pretty decent run in mid-2000s and early-2010s cinema. He plays Foster, and he actually brings a level of raw energy that fits the movie’s pace.
- Cathy Moriarty: This was a huge get for the production. She’s an Academy Award nominee (shoutout to Raging Bull). She plays Sarah, providing the emotional tether that a movie filled with testosterone desperately needs. Her performance is a reminder that the "life" doesn't just affect the guys carrying the guns; it destroys the women standing next to them too.
Why the Casting Worked (and Why It Didn't for Some)
Look, critics weren't always kind to this movie. Some called it derivative. Some felt it leaned too hard into stereotypes. But if you're a fan of the genre, those "stereotypes" are actually the draw. The Once Upon a Time in Brooklyn cast was assembled to fulfill a specific promise: a gritty, unvarnished look at a world that is rapidly disappearing.
Brooklyn today is all artisanal coffee shops and high-rise condos. This movie, and the actors in it, represent the Brooklyn of the 80s and 90s that stayed alive in small pockets well into the 2010s. When you see actors like DeMeo and Pastore on screen together, there’s an unspoken shorthand. They know the rhythm of the speech. They know how to wear the tracksuits. They know the weight of a stare. That’t something a big-budget Hollywood production often misses when they cast a "pretty boy" lead and try to teach him a Brooklyn accent in three weeks.
The chemistry between William DeMeo and Armand Assante is particularly interesting because it feels like a passing of the torch. Assante is the legend, the guy who has been doing this since the 70s. DeMeo is the guy carrying that legacy forward into a new era of independent filmmaking.
Behind the Scenes of the Ensemble
Interestingly, this movie had a bit of a journey before it hit the public. It was filmed under the title The Last Gamble, and you can still find some old promotional material using that name. The shift to Once Upon a Time in Brooklyn was clearly a marketing play to lean into the epic, nostalgic feel of films like Once Upon a Time in America.
The director, Paul Borghese, also appears in the film. This is a common trope in New York indie cinema—the director is often part of the fabric of the community they’re filming. Borghese has a long history of working with these specific actors, which explains why the performances feel so relaxed. There’s a level of comfort on set that translates to the screen. Nobody is trying too hard to "act." They’re just being the characters.
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Noteworthy Cameos and Faces
If you blink, you might miss a few other faces that have popped up in various crime dramas over the years. The movie is peppered with guys who have played "Mobster #3" or "Undercover Cop" in everything from Blue Bloods to The Irishman.
- Paul Borghese: Not just the director, but a solid presence in front of the camera.
- Louis Vanaria: Another veteran of the genre who brings a level of authenticity to the smaller scenes.
- Robert Costanzo: A guy whose voice you’d recognize anywhere. He’s one of those "character actors" who makes every scene better just by being in it.
The Legacy of the Cast
So, where are they now? Most of the Once Upon a Time in Brooklyn cast has stayed very active in this niche. William DeMeo launched Gravesend on Amazon Prime, which is basically a spiritual successor to this kind of storytelling. It features many of the same faces and the same love for the borough.
Armand Assante is still working prolifically, often appearing in international productions and keeping that legendary status intact. Ice-T, of course, is a television icon at this point, but he still dips his toes into film when the project feels right.
What's fascinating about this group is their loyalty to the genre. They aren't trying to be in the next Marvel movie. They aren't chasing trends. They are the guardians of a very specific type of New York storytelling that prioritizes loyalty, family, and the inevitable tragedy of the criminal life.
Reality Check: Is it a Masterpiece?
Honestly? No. It’s not The Godfather. It’s not even A Bronx Tale. But it doesn't have to be. The value of the Once Upon a Time in Brooklyn cast is that they deliver exactly what the audience wants. If you sit down to watch a movie with this title and this cast, you want to hear the accents, you want to see the tension in the social clubs, and you want to see a guy struggle with a choice between his blood family and his crime family.
The movie delivers on those fronts because the actors believe in the material. There’s no irony here. There’s no winking at the camera. It’s played straight, and in a world where everything is a meta-commentary on something else, that sincerity is actually pretty refreshing.
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How to Dive Deeper into This Genre
If you’ve just finished watching the movie or you’re researching the cast because you’re a fan of the "Brooklyn Mob" sub-genre, there are a few ways to really appreciate what these actors brought to the table.
Watch the "Spiritual Successors"
Check out Gravesend. It’s a series, not a movie, but it features William DeMeo and a revolving door of legendary character actors. It feels like the natural evolution of what was started in Once Upon a Time in Brooklyn.
Look for the Directorial Work of Paul Borghese
Borghese has a knack for capturing the texture of New York. Looking at his other projects will give you a better sense of why he chose this specific cast. He tends to work with people who have lived the life or at least lived in the neighborhoods they are portraying.
Follow the Independent Path
This movie is a prime example of independent film reaching a wide audience through sheer force of will and a recognizable cast. If you're an aspiring filmmaker or actor, studying how DeMeo produced and starred in his own projects is a masterclass in "doing it yourself" in the industry.
Verify the Credits
When looking for the film on streaming services, remember to search for both Once Upon a Time in Brooklyn and The Last Gamble. Depending on the platform and the region, the title might vary, but the cast—that powerhouse lineup of DeMeo, Assante, and Ice-T—remains the same.
The most important thing to remember is that this film is a time capsule. It captures a group of actors who represent a very specific New York identity at a time when the city was changing rapidly. Whether you're in it for the drama or just to see some of your favorite "tough guy" actors on screen together, the cast is what makes the experience worthwhile.