Today we’d like to introduce you to Natalie O’Sullivan Hamilton.
Hi Natalie, so excited to have you with us today. What can you tell us about your story?
I got my start right at home in Chicago with my parents, John and Julie, and my older brother, Chris. Being silly and goofing around until our sides ache and tears stream down our faces has long been a part of the O’Sullivan DNA. I always loved art and performing. I’ll never forget when I confessed I wanted to be an artist to an uncle of mine, he asked what kind and I enthusiastically responded, “A con artist!” – Obviously not understanding what that really meant, but evoking a laugh sure felt good. My parents were always supportive of my endeavors – be it painting, drawing, cooking, they were always down to let me give it a shot and see what stuck. I was a strong student in school who yearned for extracurricular – something, anything to get my ya-yas out. It wasn’t until I took a photography class in eighth grade that my teacher saw something in me – had I ever heard of improv before? I loved Whose Line Is It Anyway? And Saturday Night Live was a staple growing up in our house. She recommended my mom sign me up for a summer boot camp at the renowned Second City Theatre where they offered improv and sketch comedy classes for fellow goofball teenagers. Looking back on it now, I was probably disrupting the class with my antics and impressions and this poor lady wanted me to get out of there so the rest of the more serious students could focus. And boy, was she right! I felt so at home on stage with other gawky weirdos like myself, wearing ironic t-shirts with fish on them that said “JUST FOR THE HALIBUT” and dark-rimmed glasses to showcase how smart I was. I never went to a sleep-away camp, but comedy camp was pretty groovy.
I continued performing throughout high school and knew that acting and comedy were absolutely what I wanted to pursue. School was always a crucial venture for me. I took academics very seriously, and when faced with choosing a college where I could chase my hopes and dreams, I ended up picking the wrong one. It’s cool! It happens. Being a miserable student made me realize even more what my priorities were, and how they weren’t being met. I knew two weeks into my first semester at college that I had made a mistake. I chose to tough it out and finish the year, but I also submitted my application for a different college in the middle of my freshman philosophy class. WWDD – What Would Descartes Do? Probably algebra (not my thing). Thankfully, I was accepted and started school in the fall in downtown Chicago, my kinda town, surrounded by other creatives and performers who were truly living what they loved. It was kismet – this was the right place for me.
While I was matriculating (how collegiate!) I got such a range of experience in the worlds of theatre, television, and film. It was highly encouraged for students to collaborate outside of their majors and see what cool fun crazy art we could make working together. At school, I was featured in several students films, a live television show, and even provided voiceover for an Adult Swim online video game. Outside of school, I cut my teeth performing with my improv troupe across city stages, winning a few improv competitions, and even writing and starring in a superhero sketch revue on a Second City stage, right back where I started! I loved my experience at my alma mater so much, I actually started working at the school as an admissions representative. I was able to travel the country and talk to students who were just like me.
I balanced working and traveling with performing on stage as much as I could, be it improv, sketch, or avant-garde theatre pieces. I met fellow performers at venues all over Chicago, and in 2013, unbeknownst to me, I met my future husband Ian at an underground comedy show. What a boon! Ian and I continued to work on comedy shows together (read: family-friendly Christmas shows, to be more specific!) in Chicago until fate took us both to the East Coast – he to New York City, and I, Rhode Island. In Providence, I found an improv guild where I could write, perform, and even teach to my heart’s content. It was lovely to once again get my ya-yas out, but eventually I quit my school job and moved to Brooklyn to pursue acting and comedy for real. It was time. It was a lot of hard work, but it was always worth it to know that I was living what I love. It takes a lot of trust to get up on stage with someone and know they’ll support you, no matter what crazy shenanigans you’re about to pull. I always felt safe on stage with Ian. I always felt at home with him. I always knew he had my back. Of course I fell in love with him. Now THAT’S kismet!
While in New York, I worked as a production assistant throughout the city, jumping from photo shoots to art installations to commercials, from TV shows to comedy specials to cooking shows. I worked long hours with hard labor but I was just happy to be working and networking. I took the chipper Midwestern approach of “I will work sun up to sun down with a big ol’ smile on my face!” to every production I helped with – thankfully, someone saw that as an asset. I was asked to be an associate producer of a reality TV show. I was surprised but ready for the challenge and for the last six months I’ve been working nonstop to help make that show happen. From a PA in 2020 to an AP in 2021, I feel that I have truly bossed up and changed my life.
We moved out of Brooklyn in summer 2020, looking forward to big skies, a warmer climate, and a thriving film scene in Austin. Before we left Bed-Stuy, we made a talk show from our apartment called 100% SWEATPANTS that is an amalgam of interesting facts, life stories, and goofy bits and characters. Writing, producing, and performing our own comedy has always been our bread and butter – whatever makes us laugh, we want to share that with the world. I’m so thankful I have a comedy partner and life partner who supports me in every endeavor, who faces every challenge with me head on, and who’s always had and continues to have my back.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
That’s a funny question! The answer is a flat “no”. Smooth is too cool and sleek for me. I’m no James Bond! There’s always been bumps along the way. Navigating what you want to do for the rest of your life is a very hard decision to have to make at 17, and I think it’s messed up that we are asked to do that as a society. We put pressure on students to figure it out and let me tell you, I’m such a different person than I was when I was 17. I worked in academia all throughout my 20’s and in that time, I made several attempts to figure out what it is that I wanted to do for the rest of my life. Did I ever expect to produce a reality television show? Nope! Did I want to work at a college for the rest of my life? Absolutely not. So how did I make the leap from one to the other, and why? I had to trust my gut, and deep down I knew I couldn’t talk to students about the merits of pursuing their goals of working in the arts when I was giving 40+ hours of my life every week to something else. It was scary, but I chose to quit my salaried jobs where I felt safe and had health insurance to work as a freelancer in film and TV production. It went against all the fibers of my being that screamed “JOB SECURITY! REGULAR PAYCHECKS! A 401K!” – I cried when I knew I had to leave that behind and figure it out. It took grit. I didn’t have a regular job for months in Rhode Island and New York. I drove for Lyft. I taught improv. I worked overnight installing paper art displays, climbing 20 foot ladders and building scaffolding. Eventually, I found myself on sets with other hardworking folks who love film and TV and I learned what it takes to make shows happen. I stayed relentlessly positive because I knew I was growing, and I wouldn’t take it back for anything. I’m happy I had new experiences in new places with lots of different people, and I could draw from that to build my comedy. I hope I talked some students into living their best lives though, and I hope they pay it forward.
Appreciate you sharing that. What else should we know about what you do?
Currently, I work as an Associate Producer for Pillow Talk: Happily Ever After? Yes, there is a question mark in the title! This is a 90 Day Fiancé spin-off show where former couples from the show watch current seasons and react or relate to them. I will toot my horn in saying I have surprised myself again and again through working on this season, having zero previous experience working on a reality show before. (Should I toot my horn about that?) I rose to the occasion, learned so much about what it takes to be a producer, and thankfully Pillow Talk is a comedy so I do get to have a lot of fun with the cast at work. Thank you endlessly to my executive producer who saw something special and took a chance on me, because I truly love the work I get to do.
Outside of Pillow Talk, I collaborate with my husband Ian on comedy writing and general goofballery. We constantly bounce ideas off each other and are hoping to produce a cheeky short we’ve written in the coming months. We are currently working with our Chicago friends from Mr. Bunker’s Conspiracy Time Podcast on some super special episodes that will be debuting later this year!
One mark I’d like to think I left on New York City before I moved – I acted in a handful of music videos! I was totally “the girl in the music video”. How cool is that? It was such a treat and I was honored to have even been asked. I worked with Sweet Avenue, MAKESHIFT, Ticker Tape, and Resistor, all local New York bands.
I’m proud to have been a finalist for Red Bull Theater’s 10th Annual Short New Play Festival with my play Miniskirt. I wrote this play one night while in quarantine, inspired by Noel Coward’s Private Lives. I was one of eighteen finalists chosen out of over 500 submissions, and I hope someday to put my ten-page farce up on stage.
My love of supporting other people’s ideas is what sets me apart. I get a thrill out of being a collaborator with fellow creative folks and enjoy putting my sweet and silly spin on something. Sprinkles on the cupcake, that’s what it is. The cupcake’s already sweet enough, but sprinkles make it charming.
Are there any important lessons you’ve learned that you can share with us?
I think the greatest lesson I’ve learned in my life can be put as plainly as Ms. Frizzle from The Magic School Bus used to say – “Take chances, make mistakes, get messy!”
Contact Info:
- Email: osullinat@gmail.com
- Website: https://natalieosullivan.com/
- Instagram: @cottontailbandit, @sweatpants100
- Other: https://natalieosullivan.com/sweatpants100
Image Credits
Justin Lynk, Anthony Pasini, Julie O’Sullivan
