By: Usman Niazi Seo
Independent film has always been a space for risk-takers—directors who use small budgets and creative freedom to challenge the rules of mainstream cinema. Few embody this spirit better than Howard Goldberg. For more than four decades, Goldberg has been weaving humor, surrealism, and experimentation into the American indie film scene. His 2013 feature, Jake Squared, stands as one of his boldest projects—a meta-experiment that turned the camera inward to explore the messy intersection of memory, regret, and self-discovery.
A Story About a Story
On the surface, Jake Squared is about a filmmaker named Jake who decides to make a movie about his own life. That premise alone might sound unconventional, but Goldberg doesn’t stop there. As the story unfolds, Jake’s past and future selves start showing up on set, along with other characters who seem to exist somewhere between memory and imagination. The result is part comedy, part drama, and part surreal dreamscape.
For Goldberg, the film was a chance to blur the lines between fiction and autobiography. While not a direct self-portrait, Jake Squared reflects the questions that every artist wrestles with: How do we understand the choices we’ve made? How do we reconcile the people we once were with the person we are now? And can storytelling itself bring clarity—or does it only make the picture more complicated?
Surrealism Meets Humor
Goldberg’s filmmaking style has always leaned toward surrealism, going back to his cult debut Apple Pie in the 1970s. But in Jake Squared, surrealism takes on a deeply personal dimension. Rather than using surreal elements as background flavor, Goldberg places them at the center of the story.
The presence of multiple Jakes—each representing a different stage of life—turns the narrative into a kind of cinematic funhouse mirror. At times, the film is laugh-out-loud funny, with absurd moments of dialogue or confusion. At other times, it takes on a haunting tone, reflecting the way our past choices can feel both distant and painfully present.
This blending of comedy and surrealism has become a hallmark of Goldberg’s work. It allows audiences to engage with difficult questions—about love, regret, ambition—without the weight becoming overwhelming.
Casting the Inner Life
A project as unconventional as Jake Squared demanded a cast that could handle the strange balance of realism and absurdity. Goldberg assembled a group of actors who could bring warmth and humor to the film’s layered characters, while also leaning into the surreal elements without hesitation.
The ensemble cast helped ground the film’s dreamlike qualities in human emotion. While the concept of multiple versions of the same character could have become confusing, Goldberg’s direction kept the story rooted in the universal experience of looking back at one’s life and wondering, “What if?”
Making the Meta Work
One of the challenges in creating a meta-film is avoiding self-indulgence. Movies about movies can sometimes collapse under their own cleverness, losing touch with the audience. Goldberg avoided this trap by keeping the emotional stakes front and center.
At its core, Jake Squared isn’t just about filmmaking—it’s about the desire to make sense of one’s own story. The act of directing a movie becomes a metaphor for the way people direct their own lives, shaping narratives out of messy experiences. This focus on universal themes allowed the film to connect with viewers who might never step foot on a movie set but who understand the struggle to reconcile the past with the present.
A Continuation of a Career
By the time Goldberg made Jake Squared, he had already built a reputation as an indie filmmaker unafraid of experimentation. His earlier works, from “Apple Pie” to “Eden,” had established his interest in blending surrealism with satire and dark humor. Jake Squared felt like a natural extension of this trajectory—a film that brought together decades of artistic exploration into one deeply personal project.
It also reflected Goldberg’s multidisciplinary approach to art. As a sculptor, writer, musician, and filmmaker, he has always drawn from diverse creative languages. Jake Squared carries that same layered sensibility, combining visual inventiveness, rhythmic editing, and dialogue that often feels like literature brought to life.
Reception and Legacy
Like many bold independent films, Jake Squared divided opinion. Some audiences loved its willingness to take risks, while others found its surreal structure disorienting. But even among its critics, the film sparked conversation—a mark of success for any independent project.
Over time, Jake Squared has found its place as part of Goldberg’s larger body of work. For fans of surrealist storytelling, it offers a fascinating window into the ways film can serve as both entertainment and self-exploration. For indie filmmakers, it serves as an example of how to embrace risk and lean into originality, even when it challenges traditional narrative forms.
Why It Matters Today
In the age of streaming platforms and algorithm-driven content, films like Jake Squared stand out as a reminder of what independent cinema can do. They remind us that movies don’t always have to follow predictable arcs—they can bend time, multiply characters, and embrace the strange logic of dreams.
Goldberg’s experiment with Jake Squared also speaks to broader cultural questions. As people live more of their lives online, with digital footprints that preserve past versions of themselves, the idea of confronting “multiple selves” feels more relevant than ever. In a sense, the film anticipated the way modern life blurs boundaries between past, present, and future.
The Meta-Legacy of Goldberg
Howard Goldberg has never been a filmmaker who plays it safe. With Jake Squared, he took one of the riskiest creative moves in cinema—turning the lens on the act of filmmaking itself—and infused it with humor, humanity, and surreal imagination.
For Goldberg, the film was more than a story. It was a statement about the role of cinema in helping people make sense of their lives. And in that sense, Jake Squared wasn’t just a movie about a movie. It was, like much of his work, a surreal reflection of the human experience.
