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Conversations with Caryn Ruby

Today we’d like to introduce you to Caryn Ruby.

Hi Caryn, thanks for joining us today. We’d love for you to start by introducing yourself.
Sure, I’m a writer/performer and script supervisor, and I really really love living in Los Angeles. Growing up in Chicago, I always dreamt of living here among the sunshine and Palm Trees and working on TV sitcoms – where life was FUN! Basically the opposite of my dysfunctional and dreary upbringing. But, since I wasn’t even confident enough to speak in class – even if I knew the answer – I never really believed I could lead such an audacious life. So, for years I completely ignored my true desire.

When I got to high school, I started working out and watching shows at The Second City. I was in awe of how talented the performers were, and think to myself, “I wish I could do that too if only I was smart enough and funny enough.”

Even though I was interested in the performing arts, I ended up double majoring in Psychology and Exercise Science, and following it up with a Master’s in Kinesiology. While these degrees may not seem particularly useful for my current work, I have found that my deep understanding in both fields helps me to work well with pretty much anyone, easily step into different characters’ shoes as an actor, and write dialogue from their unique point of view (although in hindsight, the M.S. was probably overkill).

Yet, I didn’t move to LA until I was 26 because I was still afraid to admit I wanted to work in Hollywood – so I hid behind the idea of becoming a Chiropractor and enrolled in the Los Angeles College of Chiropractic. Right before I was to start, I got cold feet. Like ICE cold. I knew I wanted to help people feel better, but deep inside I knew this wasn’t it. After several financially challenging years as a personal trainer, I switched gears and fell back on my secretarial skills, settling into a day job at a big-name entertainment law firm. Not quite “in” TV, but I was closer than ever and finally allowed myself to study acting, comedy and writing.

Graduating from The Second City Conservatory was deeply life confirming – maybe I could manifest my dream after all! As I continued my studies at The Groundlings and Corey Mandell’s screenwriting program, my confidence grew. I booked some respectable acting gigs, toured with improv and sketch troupes and did stand-up comedy on the road. As YouTube was taking off, I started my own channel and continue to create and collaborate on sketches and short-form comedy – several of which have won a number of awards on the festival circuit.

Yet, there was still something missing. I felt so much joy when I was on set, which made it harder and harder to continue going back to the office. That’s when I realized I needed to find a “crew” type job so I could be on set more often than just when I was cast in something or produced it myself, and I am so grateful to have found script supervising! Not only because this “day job” has turned into a huge passion and the true manifestation of my dreams but also because I was literally not interested in pursuing any other production job! It’s amazing to be on set regularly (hello, happy place), work directly with the director all day, interact with every Key Department Head, and contribute in a meaningful way to all kinds of important and comedic projects.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I think we all wish that it could be a smooth road – I mean who wants to suffer? But unfortunately, the entertainment industry offers many, many opportunities for struggle. While of course, it doesn’t need to be this hard, I do think it’s important to have some struggle and adversity in life so you can truly appreciate it when it’s good. Especially if you’re an artist, I believe challenges can help increase your empathy and give you a deeper understanding to draw from. For me, my biggest struggles have always been in my personal life.

Without going into much sordid detail, my family origin has some generational trauma and more than our share of mental illness wreaking havoc in relationships.

Of course, I’ve also had plenty of professional struggles, but in hindsight I’m truly grateful for all the lessons and much-needed redirection. The first big one was right after grad school. I could not get a job in my concentration of Corporate Worksite Wellness to save my life. I applied and interviewed all across the country but for one reason or another – it was often “overqualified” – I couldn’t land a job doing what I had just spent so much money and time studying. I sometimes think about how my life could have turned out differently if I had gotten that job in corporate fitness in downtown LA. It was the first and only time I was “flown in” for an interview. That was super cool, but the truth of why I wanted this job so badly had nothing to do with the job – it was fine – I wanted this job because it was IN LOS ANGELES! Had I gotten it, the whole trajectory of my life would have been different! I never would have worked at the sports club in Scottsdale – the basis for the first pilot I wrote – or the gyms here in LA where I met all my friends once I did finally move. The crazy thing is that it is entirely possible that I would still be working in some corporate fitness center all these years later and never followed my true passion. I’m so grateful I never got that job!

Other struggles include two multi-car, car-totaling accidents with broken bones, financial issues, long-term relationship endings, and a regrettable time when I let a misogynistic improv teacher destroy my confidence to the point where I quit the Second City House Team I had been so excited to join.

But no matter what happens in life, I believe the job of an artist is to find a way to follow your true passion, whatever that looks like. If you ignore your purpose for too long – like I did – at some point, the universe might just step in and shake you up until you hopefully recognize you’re on the wrong track. Looking back, even though I’d probably do a few things differently now, I am thankful for all the struggles and shakeups.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I’m truly blessed because as a multi-hyphenate I get to work and find joy in multiple ways. One project that I am really proud of is the limited-series podcast I just released, “Script Supervisors: Unsung Heroes of Film & TV.” Nobody had ever done a podcast exclusively on script supervising before, and this craft and our people are truly deserving of more recognition and understanding. Plus, I’m really proud of the unique 2-part episode format I created, featuring over a dozen smart and funny script supervisors, many who have worked on Academy and Emmy Award-Winning and nominated films and TV shows.

As a script supervisor, I love working on comedic projects not only because comedy is my passion but because it’s a chance to bring all my experience as a comedy writer and performer to the job. Being fluent in the language of comedy, I can contribute much more than continuity notes. I deeply understand comedic timing and joke structure, the rule of three, etc. and can always report whether a particular joke landed. Plus, I’ll never spoil a take by laughing – no matter how funny it is! My favorite is when I can combine my skillsets, and on occasion I’ve been able to contribute to script rewrites and joke pitches, and a few times have been offered the chance to help out in front of the camera. However, because it is nearly impossible to simultaneously script supervise and act, I usually have to pass.

As a writer/performer, I’m all about dark comedy with a social or political message and am happy to share that my most recent parody short “Vadgevertising,” (where I play a misogynistic ad-man whose “specialty” is incredibly sexualized ads) has won seven festival awards to date and just screened in the Wildsound Film Festival Special Dark Comedy showcase of the best films of 2022. Another project I’m really proud of is the 15-episode web series “Baked Goodes,” that I co-created with an extraordinary team of 4 women and one awesome man, which was named an “Afternoon Delight” by Decider and “What to Watch on Marijuana’s Biggest Holiday” in Newsweek Magazine.

Not that long ago the general consensus seemed to be that everyone had to choose ONE THING and stick to that ONE THING for the rest of your life. Like are you a writer OR an actor? Behind the camera OR in front of the camera? But that way of thinking is not conducive to the creative process of a lot of people I know and I’m so glad it seems to be changing! I love that I get to be a multi-passionate creative and explore all my different interests, and can’t wait to see what’s next! For one, I am especially looking forward to shooting more in VR and on LED stages. After script supervising several times in Virtual Reality, it’s clear that’s the future of film and TV production and I am excited to be a part of it!

We’d be interested to hear your thoughts on luck and what role, if any, you feel it’s played for you?
There’ve definitely been a few strokes of luck where I was in the right place at the right time – or maybe it was fate. Years before I started writing tv pilots and spec scripts, I won a copy of Final Draft software in a raffle at the Topanga Film Festival. I truly believe it was the Universe pointing me in the right direction. That software is expensive(!) and having it from the beginning really expedited my trajectory. Another lucky happenstance is that early in my acting career, a co-star who was a Second City Conservatory graduate said I was funny and should enroll there too – which was all I needed to hear, having grown up admiring the performers at Chicago’s Second City! So, I signed up the very next day – and snagged the last spot in the Improv for Actors course, which led me to the Conservatory and then to Groundlings and then to performing and touring with several improv and sketch comedy groups. I feel extremely lucky to have had the opportunity to go on tour several times both with comedy troupes and stand-up comedians. I worked really hard, but also, I think it was tremendously lucky to have been born in Chicago where I was exposed early on to the alternative comedy scene and later was able to move to Los Angeles where I had access to some of the best teachers in the world.

For sure a lot of the circumstances in my life are due to legit good fortune, and I’m truly grateful (really!), but I also think we each have a part in creating our own luck – or lack thereof. Like if you’re on the right path (for you), there are bound to be confirmational signs along the way, but if not…your signs will show up differently (like massive car accidents in my case) to show that something’s not right. Then, it’s up to you to take action and change course – and hopefully without too many broken bones!

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Image Credits
Aymae Sulick, Ashly Covington

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