Behind the Scenes of Sid Penrose: Notes from the Writer / Director

Behind the Scenes of Sid Penrose: Notes from the Writer / Director

Like a lot of my story ideas, the concept of Sid Penrose came from a dream. It wasn’t my dream this time, however. This one came from the zzzz’s of a good friend of mine, Doug Cochrane. He presented the idea to me in 2014 and we got to work on fleshing it out. Over the years and through multiple revisions, it became the film below. I recommend watching the film before continuing with the article as there are spoilers.


If you’re still here, thank you! Sid Penrose became this enigma that matured in my brain over the years. He evolved into something different to me as my experiences became more vast. He became the personification of depression–a complete loss of hope. Yet he was also the salvation in that he was offering a way out from under this pain and misery. Was he the good guy or the bad guy in this story? 

Though he was still unnamed, five years later, the idea of this salesman of death had not lost his hold on me. In that five years, I had watched my girlfriend’s family endure the heartache and suffering of losing her brother to suicide. I had no way of comforting them in their grief. But that is when it all clicked for me. This wasn’t a story about death. It was a story about life and finding a way to overcome the obstacles that hold us down and make us lose hope. After all, I have had my own battles with depression, as a creative person, which you can read about here

I dug out the old version of the script and set to work on the rewrite. I needed a way for Charlie to actualize Sid Penrose. I did that by having Charlie draw his pain after seeing an article on Bored Panda where artists did just that–they gave a face to their depression by drawing it.  The drawings are heartbreaking but they are also something real and tangible and unique to their own battles with depression. 

So that was my answer. I’d have Charlie draw Sid into existence. My next hurdle was to find a way to give Charlie a reason not to sign his death certificate. Because sometimes we are so blinded by our despair that reasoning with ourselves is simply not possible. I needed an act of divine intervention if you wanted to call it that. I always had a stain written into the script but I never consciously knew what it signified. But that was my answer. Charlie’s roof was leaking and while it seemed like yet another aspect of his life that was falling apart, it actually ends up being the very thing that saves him. 

Poof! There it was. That was my story. Stories don’t always come to us all at once. It’s fun when they do, but this one needed time to marinate–to settle into its truest form. Writers often talk about simply being a conduit for their ideas rather than the one who generates them. That was certainly the case with this one for me.


While the script did go through a couple more iterations, Justin Strandlund and I went to work on actually bringing this thing to life. We decided that this would be our first West Coast film and to do that, we enlisted the help of a friend who had spent the past ten years producing content in LA. He put together a budget for us and started assembling the necessary crew. It quickly became evident that this would be our biggest undertaking so far and that while we had built up a bit of our own nest egg through various corporate work and paid gigs, we would need some help in raising the funds needed to throw adequate resources at the project.


Fundraising as a filmmaker is not for the faint of heart. It adds a whole other element to the pre-production process. We ended up going with IndieGoGo as our crowdfunding platform because of the fact that we didn’t know for sure we’d be able to raise the amount of money that we were asking for.  

While the site made it fairly intuitive with easy-to-use templates, we still had to spend a great amount of time reaching out to our network of family, friends, and acquaintances asking them for money, which is not something we enjoyed doing. Why would anyone want to just give us their hard-earned money? Well, we were fortunate that people did end up believing in the project enough to donate and we are very grateful!


Once the funds were in place, it was time to cast our film. With only two roles to cast, we felt confident going into it that it would be a fairly easy process. This was only half correct. We used an online casting platform called Breakdown Services and quickly got a slew of submissions for both the role of Charlie and Sid Penrose. After watching Kyle Mac read for the part, we knew we had found our Charlie. He simply was Charlie. Robert Altman is attributed with saying that 90% of directing is simply casting the right person and I mostly ascribe to this sentiment, especially with this film. 

However, the role of Sid proved to be vastly more difficult. We had a whole bunch of “well maybes,” but no one that really stood out. Sid Penrose, being the enigmatic figure that we wanted him to be, had to be special. He had to stand out and be something unique. He had to bring a gravitas to the role but at the same time be completely unpredictable. He had to be sympathetic yet direct. We were less than a month away from shooting and still had not filled the role when we received the self-tape from Bill Kates:

We had found our Sid Penrose and we were ecstatic. It was time for a rehearsal so I drove up to LA to meet Kyle and Bill face to face for the first time. It was clear right away that we had made the right decision in casting them. They not only understood the characters that were written on the page but they brought their own ideas that further crystalized them.

It was also the first time that it was brought to my attention (by Bill) that this film had a Twilight Zone sort of feel to it. I was thrilled to hear this as I had no conscious intention of making it that way. But it made complete sense considering my affinity for the show (the Rod Serling version). It was then that I knew that this film could appeal to more than just the subsection of people who had dealt with depression and suicide in some form. It could resonate with a wider audience of mystery and supernatural connoisseurs.

Rehearsal isn’t just for the actors. During that trip, I also had a chance to meet with my Director of Photography, Emil Chang, and his gaffer, Emre, to scout the location and discuss a very broad scope of how the lighting and blocking would be set up. This meeting proved to be invaluable as we had just one day to film the 12 pages of script.


A week later I was back in LA to meet with Emil, to work on the storyboards and shotlist. This would be our last chance in person to plan out our shoot day. The meeting went great. We had a game plan in place and went our separate ways. 

Somewhere in between that meeting and our shooting date, which was only about a week away at this point, things began to unravel. I have always put a lot of pressure on myself and this film held a lot of personal feelings for me, which only exacerbated that pressure and stress I was experiencing. 

Two days before the shoot, with Justin, my producer, and 1st AD, scheduled to fly into LAX the next morning, I seriously considered pulling the plug on the whole thing. I was overwhelmed and ready to find a way out of this project that I no longer felt confident in my ability to pull off. If I did so, I’d still have to pay the entire cast and crew what I had agreed to despite the fact that I’d have nothing to show for it. But that was how afraid I was.


Unlike Charlie in the film, I had no “divine intervention” that pulled me through to the other side of that fear, but I made it. Maybe because I had too many people counting on me. Or maybe because I thought that my fear came second to the importance of the story. I honestly don’t know what it was, but two days later, I was on set and making the movie. 

A funny thing happens to me on a film set. All the stress and pressure disappears. It’s no longer in my hands. I’ve done all I can once action is called and it’s up to the actors and crew to do their thing. It’s kind of like magic. And it’s that feeling that drives me to make movies. I love every second of it. I get lost in this illusion of reality. It’s actually not “kind of like magic”–it is magic.


Despite my love for making movies, the words “that’s a wrap” also have a sorcery to them, and hearing those words on this film, at this particular point in my life, meant everything to me. I went outside and cried tears of joy and/or relief at it all being over. I called my girlfriend, Jamie, just to hear her voice–to reconnect me to the real world and release me from the spell that this film had held me under for so long. 

That night, despite feeling a thousand pounds lighter, I became physically ill–like my body had done all it could to get me to this point and now simply gave in to the stresses it had endured. Even still, it was all worth it and it was difficult to wipe the smile from my face.


We’ve said it before but a film is, in essence, made three times. There is the actual writing of it. Then there’s the filming of it. And finally, there is the weaving together of these two elements in the form of editing or post-production. In other words, the puzzle pieces are there–now it’s how we choose to assemble them. Because, unlike a regular puzzle, there are no set parameters that we have to stick to. We can arrange them in whatever order we choose to–the way that best serves the story in a clear and concise manner. 

We ended up spending nearly two years in this purgatory of post-production, which I’m sure I don’t have to tell you is way too long for a short film to spend in post. It just seemed like hurdle after hurdle was set before us causing us to have to find creative ways to pivot and reassess. 

But we persevered because we continued to feel just as strongly about this film as we did when we first set out to make it. And like the story itself, sometimes all we can do is endure and persevere through obstacles and setbacks because there’s something really fulfilling on the other side. I can absolutely attest to that now that the film is out there for the world to see and no longer festering inside of my monkey brain. 

I hope this helps people not only in their filmmaking journey but in their life journey because life imitates the filmmaking process in so many ways. Please consider sharing the film as we truly believe in its message of hope and finding the strength to fight another day.

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