A good documentary entertains, but a great one illuminates as often as it plays to our need for a certain edutainment. It can be difficult for a documentary filmmaker to step outside his chosen subject, to provide a bit of objectivity on whatever he’s covering. But those who can offer both their personal and professional estimations on any given idea are the ones who can truly engage with their audiences on multiple levels. And their films are better able to convey both the truth behind public assumptions and researched facts.

And when it comes to placing a subject within a particular framework, specifically in regards to its influence and modern mystery, the life and times of singer Sly Stone are perfectly suited for this kind of examination. When actor-director Michael Rubenstone set out to discover what happened to Sly Stone after his sudden departure from the mainstream and his mammoth success as part of Sly and the Family Stone, it would be 12 years of trying to locate a man who didn’t necessarily want to be found.

During a rough stretch in his own life, Rubenstone set out west to California to try to get work as an actor, and on the way, he rediscovered an old friend in the form of Sly Stone and his music. Once there, he found some work, but the thought of Sly never left his mind. His fascination with and love of the man’s work led to the formation of an idea, one that would come to define the next decade of his personal and professional life. That idea was “On the Sly: In Search of the Family Stone,” a documentary that was to finally reveal what had happened when Sly abruptly disappeared from public life.


The infectious joy that Rubenstone obviously holds for Stone’s music is the driving force behind his desire to meet the man. At the start of his journey, you can feel the life and ecstatic wonder pouring out from him as he begins a slow climb to his goal. With interviews from family members and various musicians who performed with him, Rubenstoneslowly begins to get an idea of who Sly was-and it isn’t always a flattering portrait. In fact, the more he digs, the more bizarre and convoluted the actions and motivations of his hero become.

Through concerts, reunions and the odd important tip from past associates of Sly’s (including a gloriously crazy visit to former manager David Kapralik’s home on Maui), Rubenstone pieces together the history that leads from Sly’s time with the Family Stone to his his last public appearance at the 1993 Rock and Roll Hall of Fame induction ceremony for the band. For every bit of ground that he gains in his search for more information, there are moments when the entire enterprise seems to grind to a halt-and the film seems destined to document a valiant failure. But Rubenstone’s determination and adoration of this man keep him going despite all obstacles.

We see the frustration on his face as each setback is revealed, but we also see the joy when new information seems to land at his feet. And though this experience would cause him to question himself and the direction of the film, that love for music never abandons him. He sees the fan and the professional battle it out for control of his actions, with the fan invariably winning out every time-and to see this kind of unmitigated wonder drive a man to pursue his dream is a miracle not easily overlooked. Throughout “On the Sly,” we’re given multiple versions of Sly Stone. Someone even goes so far as to liken his actions to an actor taking on different roles for different people in his life.

In the end, we’ve seen so many variations of the man that we’re unsure which is the true personality. But that hesitancy regarding the veracity of what we’re seeing doesn’t hamper Rubenstone’s enthusiasm for the project. If anything, with each course correction, he’s filled with a renewed resolve to finish this film no matter the consequences. And in that regard, this film is as much about his own determination as it is the investigative hunt for Sly.

“On the Sly: In Search of the Family Stone” offers no easy answers about who Sly Stone was and what caused him to fall from the spotlight. There are passing references to drug and alcohol abuse and the waning mainstream popularity of his music, but these facts are less important to Rubenstone than the mental state of a man who would rather live in an RV than set down permanent roots. This film doesn’t diminish the legacy of a once-great musician, but it certainly brings up questions that some people would rather not acknowledge. In his quest for information about his musical idol, Rubenstone asks these hard questions and discovers the turbulent and volatile life of a man who seems to have abandoned his genius.

Joshua Pickard covers local and national music, film and other aspects of pop culture. You can contact him on Facebook, Twitter or by email. The opinions expressed in this column belong solely to the author, not Nooga.com or its employees.

Updated @ 9:08 a.m. on 4/10/17 to correct typographical errors.