Meet Brian O’Sullivan | Singing Comedian & Commercial Actor

We had the good fortune of connecting with Brian O’Sullivan and we’ve shared our conversation below.

Hi Brian, what was your thought process behind starting your own business?
When I was 10 years old, I wanted to be Jim Carrey. The idea of making people laugh for a living was always extremely intriguing to me. After getting a degree in theatre from UNC-Greensboro, I moved to Chicago to further hone my skills by studying improv with Second City, iO, The Annoyance Theatre, and Comedy Sportz. I had grand ideas that my acting career was going to just fall into my lap because I had “done the work” and taken all of these classes, and dedicated so much time and energy to the craft. But, shockingly, that is not how an acting career typically goes. So, I needed to come up with a backup plan to pay for bills while I waited for this acting career to takeoff; preferably something outside the realm of the hospitality industry (though that has always been an on again off again part of my life post graduation). As a child, I also really loved listening to “Weird Al” and his comical songs. In fact, I would often write parodies of songs on the radio and sing my lyrics on top of the radio whenever the original song came on. Back then I didn’t have the means to find instrumental tracks or even stream the original song whenever I wanted; I had to wait for the specific song to come on the radio, and hopefully record the song to a cassette that I could then rewind and playback whenever I wanted to. In college, after writing silly songs for my friends for nearly 10 years, I decided to learn the guitar, so I could just play the songs whenever I wanted. So, when acting didn’t immediately take off for me, I started renting out theatres around Chicago, and would do all my own publicity and fill the shows with friends from work, or friends of friends, or just anyone who would take a flyer (I did a lot of barking around town as a 22 year old). I filmed a few of these shows, and within a year, I found myself with a college agent, and shortly after that, I began touring the country, headlining colleges and comedy clubs as a “singing comedian.” It all sort of really took off from there. So, my main source of income was sprung from necessity to perform, as well as my pure driven passion to make people laugh.

Alright, so for those in our community who might not be familiar with your business, can you tell us more?
I find it funny how often I will tell someone I’m a singing comedian, and they look at me like I’m speaking another language. Aside from it being exactly what it sounds like, it’s also pretty popular in comedy: “Weird Al”, Flight of the Concords, Stephen Lynch, Bo Burnham, Tim Minchin and even The Bloodhound Gang or Tenacious D. I play the guitar and sing funny songs that I wrote. And if people aren’t laughing, I play the guitar and sing songs that I wrote. I think there is a little piece of every act I mentioned above in my own style and performing. I am most popular online for my parodies (Weird Al), I play guitar and can carry a tune (Stephen Lynch), my original material often makes you think (Bo Burnham), and I love using the English language to keep my material clever (The Bloodhound Gang). When I first began performing, I really only knew of Weird Al and Stephen Lynch. One was world famous for highly produced, very hilarious, song parodies, and the other guy was a regular performer at comedy clubs, colleges, and had one or two tv specials. So, I knew that was an avenue that I could also pursue, without needing to be signed to a record label, or have a band perform with me every night (although, that would be a dream!). So that’s what I did. A comic, but with a guitar. A one man show fit for a small hole-in-the-wall comedy club, or a 500 seat theatre at a college campus. I began touring colleges, after showcasing at a regional conference for the National Association for Campus Activities (NACA). I became busy enough in my second year, that I had to quit my waiting tables job just because I was not in town often enough. Traveling the country as a solo act, with no crew, and no one in charge of you but yourself, was always very rewarding to the artist and performer in me, but also isolating, being in my mid-twenties, having moved out to Hollywood to become the next Jim Carrey, only to now rarely find myself in Hollywood at all. But through it all, I have retained a strong sense of discipline; making arrangements in both performance styles and traveling, all on my own with rarely anyone else’s physical guidance. It all definitely made me more independent, but also allowed me to show myself how mature and responsible I was becoming as a young adult. In fact, in the nearly 15 years I have now been doing this professionally, I can say that I have only ever missed a show one time. And it’s because the plane didn’t take off, due to weather. BUT that show was rescheduled for a a couple of weeks later, so really, I’ve never missed a show. Just had one delayed a little bit.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
I’ve been in Santa Monica for the last 14 years, so when my friends come to visit, we do the normal LA must-sees (Chinese Theater, Walk of Fame, Hollywood sign, Disneyland, etc…), but I like to keep it local if I can. I really enjoy performing or going to see shows at The Laugh Factory or The Comedy Store, but I love the Westside Comedy Theatre in an alley behind the promenade in Santa Monica. It’s such an intimate space, and the people that run that spot are just friendly people who love comedy. It’s like hanging out with friends at a party, and the audience all just feel like friends of your friends that you now get to hang out with. I also love there is no drink minimum there, which makes the comedy feel more special for some reason. Otherwise, we’ll definitely go check out the Santa Monica pier and beach. Usually wander down to Muscle Beach in Venice Beach. As for food, I genuinely love every spot I have waited tables at in the past in Santa Monica. So, whenever friends come to visit, it gives me a good excuse to go get my old favorites (and sometimes catch up with old friends who may still be working there). Those spots include Stella Barra Pizzeria, Blue Plate Oysterette, and Cassia. I also love checking out live music at Harvelle’s or TRiP of any given night of the week.

Who else deserves some credit and recognition?
I mentioned it earlier, but Jim Carrey was the sole reason I thought that a career of making people laugh was even a possibility. Then in college, I auditioned, and got into a local improv club called The Idiot Box. Unbeknownst to me at the time, the owners of that club, Jennie Stencel and Steve Lesser, would not only become some of my absolute best friends I would ever make, but they also became my main mentors in comedy. I owe a great deal of gratitude to the both of them for kickstarting the professionalism of my comedy career. Until I met them, it was all just for fun and to make people laugh. They helped me understand more about why and how comedy works, and encouraged me to write and perform in ways I had never considered before. I also owe a huge debt of thanks to one of my best friends from high school, AJ Schraeder. To this day, he is still one of the absolutely most brilliant comedy minds I have ever witnessed. He and I would write a lot of comedy as extracurricular work in high school drama, and we meshed very well. He loved to write more than perform (though he’s an incredible performer in his own right), and I loved to perform more than write. So we often wrote stuff to our strengths. He actually even helped me write a one man show when I was in college that was a 45 minute, 17 character, parody of classic theatre plays, in which I played all of the characters in real time, basically throwing myself around the stage, and sweating profusely, as I barreled from one character to the next through every scene. I also have to credit my mom, dad, and entire family. They all have been incredibly supportive of me and my endeavors since I was a child, and no one in my family ever doubted whether or not I could or would do this for a living. I like to joke that I would be funnier if my family wasn’t so supportive of me, but I guess I’ll take the lack of trauma for a healthy, productive head on my shoulders any day. There are dozens of others that have supported me throughout my career, and I would not be where I am today without their support along the way.

Website: www.brianosullivan.com

Instagram: @bocomedy

Twitter: @bocomedy

Facebook: www.facebook.com/bocomedy

Youtube: YouTube.com/brianosullivancomedy

Image Credits
James Reese (main photo only)