We were lucky to catch up with Jack Mccafferty recently and have shared our conversation below.
Jack, looking forward to hearing all of your stories today. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.
I feel like the only way to get ahead in the film industry is to take risks. To bet on yourself. If you’re not willing to bet it all on yourself, then why would anyone else? This was my thinking when I set out to make my first feature film, Dreaming of You.
I have never had a lot of money. For the most part, I would work just enough to afford to make a small project that would take up a lot of my time. Then after the pandemic hit, I found myself in an odd situation. I had weirdly been one of the few people who actually got a better job than I had prior to the world shutting down. It was a contract gig, but once it ended, I suddenly had more money than I ever had before. Not a lot by most people’s standards, but certainly more than I was used to having.
Now, a sensible person may have put that money to smart things. Maybe make a dent in my student loans. Maybe buy a car so I wouldn’t be forced to keep taking the bus everywhere. Well, I guess I’m not a sensible person, because I knew that I would never forgive myself if I didn’t give myself the chance to make a feature film. I had to bet on myself even if it meant I’d go broke doing it. I was willing to risk ending up working at Chipotle to pay rent and eating mostly rice and beans for dinner for three years (yes, both those things happened) if I could finally make a movie.
So, I put 15 grand of my own money into making my first feature film, Dreaming of You. I then raised 10 grand more from Seed&Spark from some amazing people. We shot the film, and I spent all my time working on it. It would be mild to call it a labor of love. It was a full time job. Took up all my time. And even after making it, it took even more money to get it to festivals for people to see. I don’t know how much I invested after it was done, but I think it’s close to the original 15 grand investment by now.
But, I wouldn’t change a thing. Because I got to premiere my film at the world famous TCL Chinese theatre. We then went on to get an honorable mention for the grand jury prize at Dances with Films. For a film with our small budget, that’s insane. Sitting in that theater, listening to the audience laugh, I knew the risk paid off. My team and I had made something really special.

Jack, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I became a filmmaker because the only thing I ever truly loved doing was making people laugh. You couldn’t pay me to do my French homework, but I would spend hours and hours cutting out scraps of paper to make my own makeshift stop-motion video for a single 20 second gag. I hosted pretty much everything at my highschool. Talent shows. Fashion shows. Anything that could get me in front of an audience. This led to me starting standup at 16. My buds and I would shoot sketch shows on our flip cameras (RIP) and by the time people were looking at colleges, my father had signed me up to tour Drexel University as a film major. I started a sketch show my freshmen year and got the school’s most prestigious scholarship all because the dean saw the show and loved a dick joke I wrote. I am very proud of this.
Post school, I’ve made a ton of shorts, animated web series and projects that have won awards at festivals and online venues. Now, I even have a feature under my belt and am working on another. I’ve come a long way from the kid who spent so many days in detention for being “disruptive.” If I could travel back in time to talk to that kid, I’d say, “Keep doing what you’re doing. This all pays off.”
My filmmaking style now stems from my want to use my emotional truths in life to tell stories that will both make people belly laugh and feel things on a deeper level. The old cliché is “I laughed. I cried.” Well, I want to make films like that. Humor and heart. And mix in cool fun stuff that I would have wanted to watch growing up. A lot of my work involves animation and mixed media because that stuff is just fun to me. I guess at the end of the day, I still just love making stuff because it makes me feel like a kid in the back of the classroom giggling to himself as he prepares a bit to share with the rest of the class.

What can society do to ensure an environment that’s helpful to artists and creatives?
The best way society can support new creatives is to take a chance on their work. I know we all like our comfort zones, especially when it comes to the media we ingest, but if we want new voices to come up in our culture, we need to listen to them when they’re still small. Watch an indie film you stumble upon on Tubi. Recommend it to friends. Buy a film on Vudu that doesn’t have a multimillion dollar budget. Go to a film festival screening. There’s gold in those hills. Especially go to film festivals as the energy there can be a lot of fun. Yes, some days you just want to watch the same old episode of the Office for the millionth time. But you could also spend that time watching some off the radar thing that may end up being your new favorite. And then, once you find that new filmmaker or artist, you can brag about how you knew about them before they got big. You then get the hip cool bragging points for supporting new talent. Don’t you want to seem hip and cool?

Is there a particular goal or mission driving your creative journey?
At this point, the goal of my career is to be able to keep making stuff. I know, that’s a classic answer, but it’s true. I just want to be able to make my projects. It’s what I love and if I can do so in a sustainable way, then I’ve won. Making a living by entertaining people has always been the goal. Selfishly, it makes me feel good to make others feel good. I’m also not cut out for typical work. I’m much more suited for silly crap.
Contact Info:
- Instagram: https://www.instagram.com/sexyjackmccafferty/
- Youtube: https://www.youtube.com/@JackMcCaffertyFilms




Image Credits
Robert Tapaltsyan
Anthony Marotta
Jack McCafferty

