Meet Bailey Pless | Writer, Comedian, Rapper

We had the good fortune of connecting with Bailey Pless and we’ve shared our conversation below.

Hi Bailey, why did you decide to pursue a creative path?
When I first learned to read, all I wanted to do was be an author. I used to read this gritty 80s reboot series of the Hardy Boys & Nancy Drew where they solved murders & fought terrorists. So of course, for our homework writing prompts, I also wrote stories about solving murders and fighting terrorists. Even on the nonfiction prompts, I would find a way to twist it. For example, if the prompt was “who is your role model and why?” I’d make up a story about my mom kickboxing an arsonist at her office. I don’t know if my first grade teacher was confused by these papers or completely terrified.

As I grew up, I found comedy the same way most do – I made my bullies laugh so they’d tolerate me. People went from calling me a weirdo to repeating my jokes louder to the class and taking credit for them. I was also obsessed with rap music, but not top-ten radio rap like everyone else. I was the only kid at my rural north Georgia middle school who could quote 30 Rock and E-40 in the same breath.

I love comedy & music too much to do anything else. I truly believe it’s the reason I’m alive. Just like I couldn’t turn it off during those first grade writing prompts, how could I stop now? For a while, my backup plan was to become a detective like Nancy Drew, but I’m way too uncoordinated and distracted. If I were to investigate a crime scene but a cool song was playing next door, I would miss every single clue. Best if I stick to playing with fictional stakes, not real ones. Giving people an escape through laughter is the only profession for me.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I stay as busy as possible, because I want my brand to be multifaceted.

I used to spend every free moment *only* writing pilots and specs, but lately I’ve gotten addicted to standup comedy. Telling a joke and hearing a laugh feels a little different than typing a joke and hearing the refrigerator kick on. My ultimate goal is to be a showrunner, so of course I still write — I’ve just found that standup makes me a better writer, plus it lifts my spirits exponentially.

I also produce, edit, and cohost a comedy podcast called The Least Famous Ryan. We have a blast recording it, and it creates a great opportunity for my other creative friends to promote themselves. We improvise bits about everything, roast each other, and have interesting conversations with talented up-and-comers. It’s like a release radar for the next generation.

For my rap music, I go by the name Triple///P. I’m working on an EP of party music with a friend from the IE, Curtis Boy. We already dropped our first single, “My B Go to Work.” Curtis is a mastermind when it comes to hooks. Unlike other comedy rap crossovers, I deliver like a real rapper – you have to pay attention to catch the jokes. If the song came on at a party, you’d think Bay Area, not SNL. It’s crazy, my #1 inspiration is E-40, but my accent is more Yung Gravy. I’m not claiming to be on their level by any means, but the song’s really fun. This whole EP’s gonna be wild.

Regardless of the medium, I’m a writer at heart. In the future, I’m looking to prove myself as a staff writer on a TV comedy and eventually work up to pitching my own shows. For now, I’m using every available platform to create unique content and collaborate with outstanding people.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
TACO STANDS. EVERY. DAY. My friend will eat their weight in chorizo or I’ve failed.

We also have to hit up shows every night. There’s such a mix of local excellence and nationwide names that perform here, you can have a great night out regardless of your budget. I’d check out whatever’s happening at the Palladium, Largo, Elysian, Wiltern, etc. If we’re in the improv mood, you can’t go wrong with The Pack Theater.

For day trips, there are so many hikes around here. My favorites are Point Mugu, Brand Park, and anything in the San Gabriel area. If it’s winter though, we’re going snowboarding at Big Bear. I’ll embarrass myself (very uncoordinated), but it’s so much fun!

But no LA trip would be complete without donuts. Dad’s Donuts in Burbank has the most magnificent, glorious, body-tingling-with-sensation blueberry-filled donut you’ve ever laid eyes on.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I would be nothing without the love and support from my family and friends back home. I’m forever thankful to my parents for encouraging creativity and learning.

Twin influencers Deja and Di-V absolutely transformed the way I view online engagement and my stage presence. If it weren’t for their tough-love critiques, I would still be treating standup like prose and getting no laughs. They, along with our friend Steven Oriee, really taught me how to appreciate being present in the moment instead of letting anxiety wear me down. They also introduced me to my frequent musical collaborator Curtis Boy.

Ryan Reid (“The Least Famous Ryan”) is my podcasting partner whose energy is contagious. He inspires me to work harder and have more fun any time we’re working together. He also likes to do a little bit of everything, and no conversation with him is ever boring. We never would have realized we could make a great podcast together if it weren’t for our friends Aly Bay & Michael Gomez — our fiercest supporters.

Finally, Jeremy “Gumbo” Christian has also given me so many standup opportunities and expert advice along the way. He helped me find confidence and showed me how to push further. You can catch him at shows all over the country and it’s always a great time!

Website: https://www.tiktok.com/@baileyplesscomedy?_t=8pS2lqxx4zy&_r=1

Instagram: https://www.instagram.com/baileyplesscomedy/

Linkedin: https://www.linkedin.com/in/baileypless/

Youtube: https://www.youtube.com/@TheLeastFamousRyan

Other: Spotify: https://open.spotify.com/artist/60NqbFTulezTh2Gl8GAfuy?si=P69ifNQcSECEZ2PGo2lLjw

Podcast: https://open.spotify.com/show/24dEngE3uHxBXX2l1SX6HI?si=4ySzkOXnQOGyD728vljA6g