Fire: you have to be passionate about what you’re doing. If you phone it in, your audience will know. This is why college theatre productions are often excellent: everybody wants to be there.

As a part of our series about creating a successful career in theatre, I had the distinct pleasure of interviewing Charlie O’Leary.

Charlie is a Chicago-based playwright, lyricist, and librettist. He is an alumnus of the 24 Hour Plays: Nationals, the BMI Workshop, the Brooklyn Generator, Crashbox Theatre Company’s Write Play Launch, the Fornés Playwriting Workshop, the Project Y Playwrights Group, and the Road Theatre Company’s Under Construction Playwrights Group. His plays and musicals have additionally been developed and presented by the Artist Co-op, Brooklyn Rep, CAP21, the Dare Tactic, Dartmouth College, Dixon Place, Dreamwell Theatre, the Flea Theater, the Fresh Fruit Festival, the Habitat, the Iowa New Play Festival, Jersey City Theater Center, Loading Dock Theatre, Middle Voice at Rattlestick Playwrights Theater, the PIT, Pipeline Theatre Company, the Players Theatre, the Samuel French OOB Festival, Shuga Pie Supreme, the Tank, and the University of Notre Dame. His short works have been published by Methuen Drama, Smith & Kraus, and Theatre Now New York, with licensing by Music Theatre International. He has been a finalist for the Alliance/Kendeda National Graduate Playwriting Competition, the DVRF Playwrights Program, the O’Neill National Playwrights Conference, Sanguine Theatre Company’s Project Playwright, the Seven Devils Playwrights Conference, and the Woodward/Newman Drama Award, as well as the recipient of a New York Innovative Theatre Award and an Iowa Arts Fellowship. His song “A Date” (music by Helen Park) was a selection of the BMI Workshop Smoker; his songs have also been performed at places like 54 Below, Don’t Tell Mama, the Duplex, and the West End Lounge. MFA: Iowa Playwrights Workshop.

Thank you so much for joining us in this interview series! Can you tell us the story of how you grew up?

Seventy-five years ago, in my rural hometown in Western Pennsylvania, my grandpa founded Fritz Pianos and Organs underneath his half of the duplex-style house where he and my grandma went on to raise my mom and her three siblings. Half-a-century later, after my grandpa passed away and his sons took over the store, my mom bought our family a Clavinova so that I could learn to play. Piano led to trumpet led to euphonium led to musical theatre led to my first-year advisor’s office at Notre Dame, where an authoritative woman in cat eye glasses told me to pick up a second major so that I would stop wanting to kill myself, or worse, transfer schools. The following year, over in the Debartolo Performing Arts Center, the playwright Anne García-Romero began teaching classes where she assigned plays we hadn’t read in my small Catholic high school — plays by Julia Cho and Tony Kushner and Maria Irene Fornés — plays within whose pages, I later realized, I finally began to grow up.

Can you share a story with us about what brought you to this specific career path?

When I was in high school, I spent hours playing, writing, and designing ARGs, or Alternate Reality Games — interactive multi-platform stories that take place over weeks and months, via YouTube and email and chat rooms — and once, in a game I wrote for, at a live event in Boston, which at age sixteen I sold my parents as a college visit. It was there, in Boston, that I first experienced what it was like for an audience to respond live to my writing. Sixteen years later, I’m still chasing that feeling.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Too many to count! Theatre teachers encouraging me from high school to college to grad school, friends passing along my work to their friends, folks who ran writers groups who took a chance on an inexperienced playwright. Even the short version of this list has at least a dozen people on it.

You probably have a lot of fascinating experiences. Can you tell us the most interesting story that happened to you since you began your career?

August 2022: Biden is president, Monkeypox is raging, I’m living in Iowa. Open on: me, in the basement of Joystick Comedy Arcade, reciting a poem about the time I lost my anal virginity, which was one week prior. On the street after: I smoke a cigarette with a straight man and his brother and his girlfriend and her brother and they all come to my apartment to play that version of Mario Kart where you drink a beer every lap. Dissolve to: I’m walking to L&M Mighty Shop to restock on light blue American Spirits — Wait, did you mean a story about theatre? One time I was in an elevator with Halley Feiffer and she asked where I bought my smoothie. Anyway, I got hit by a car.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I was in the BMI Workshop, as part of the curriculum I was required to write lyrics for a comedy song adapting a scene from Clybourne Park. Out with friends to Bea on 43rd Street, I couldn’t stop complaining about how much I hated the play. I didn’t notice until later that Bruce Norris was sitting exactly two (2) tables away. I already knew the Two Block Rule –always walk at least two blocks from the theatre to talk about the show — but that day, I learned the Two Table Rule — always assume you’re at most two tables away from Bruce Norris.

What are some of the most interesting or exciting projects you are working on now?

Right now I’m most excited about An Axemas Story, which opens at the Players Theatre in NYC on November 30th. I started writing book for this show in 2020 after two friends from the BMI Workshop, Patrick Spencer and Anthony DeAngelis (who wrote great Clybourne Park songs), approached me and said: “Let’s write a musical parody of 80s slasher films, set on a Christmas tree farm, and told from the perspective of the trees.” I said: “What?” And then a few hours later I said yes. Here’s a synopsis:

“It’s Christmastime in Tree Town, and all the trees are dying to look their best. But after a string of disappearances, Small Paul (the puniest tree in town) and Noel (who the narrator forgot to cast) begin to question Tree Town’s relationship with the venerated Farmer Todd. Will this unlikely duo crack the case before the annual Christmas Pageant?”

So if you want to ring in the Christmas season with a darkly silly musical for adults, full of tree puns, Reagan-bashing, and 80s-inspired songs performed by some of the most hardworking and hilarious young actors in the city — come check it out! Tickets are available on TodayTix, TDF, and other platforms, or you can learn more at

You have been blessed with success in a career path that can be challenging. Do you have any words of advice for others who may want to embark on this career path, but seem daunted by the prospect of rejection, lack of support, or failure?

In grad school, my professor Megan Gogerty would often say: “Process is all.” You have very little control over what happens with your career. Every break you get — and it’s usually a series of them, a bunch of little breaks rather than one big one — will involve some element of luck. You can go years without reaching what might seem like the most baseline goals — so if you’re focused on getting into a certain festival or winning a certain prize, you’re likely to be disappointed. But if you embrace process and continue making theatre in whatever form you can, someday, you’ll look around at all your friends who stuck it out and marvel at how successful they are — and this will be uncomplicated, because a rising tide carries all ships.

Which tips would you recommend to your colleagues in the live performance industry to help them to thrive and not “burn out”?

Learn to say no. I’m terrible at this. But if a project doesn’t (a) feed your soul, (b) advance your career, or © pay your bills, don’t do it. Every project you do should give you at least one of those three things.

Thank you for all that. This is the main question of our interview. What are your “5 Things You Need To Create A Highly Successful Career in Broadway, Theater or Live Performances” and why? If you can, please share a story or example for each.

If you want to succeed in theatre, all you need to remember is F.A.R.T.S.:

Fire: you have to be passionate about what you’re doing. If you phone it in, your audience will know. This is why college theatre productions are often excellent: everybody wants to be there.

Audacity: you have to be willing to fail. You have to be brave and bold and willing to mess it all up. If the work doesn’t scare you at all, you’re probably on the wrong track.

Rigor: respect your audience’s time and present them with work of substance. Spend an hour on every minute the audience watches onstage. If you think you’re getting away with something, you’re not.

Truth: as storytellers, we are always trying to better understand ourselves, each other, and the world. Only stories with a core of emotional truth can help us do that.

Support: theatre is a collaborative art; the connections you form with other artists, short-term and long-term, are what will allow you to thrive in this challenging industry.

For the benefit of our readers, could you describe how the skill sets you need in a theater performance are different than the skill-sets you need for TV or Film?

In writing, the conventional wisdom is that film is a visual medium while theatre is an aural one, with TV somewhere in between. There are obvious and major exceptions to this, and it’s not a true dichotomy (plays have visuals! movies have sound!), but it tends to hold true that a playwright’s best tool is their ear, while a screenwriter’s is their eye.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Massive wealth redistribution (i.e. no more billionaires), make it intersectional, and nothing for police/prisons/military. Everyone would be better off, even the ex-billionaires (because fewer people would tweet about guillotining them).

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Love is paying close attention.” For many years I attributed this to Cheryl Strayed, but I don’t think she said it, or at best this is a bad paraphrase of something she said. But still — it’s true! Being present — paying attention, closely observing — is a way to show care. This is true in theatre as in life.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

I’d love to get coffee with Larry O’Keefe and pick his brain about writing Bat Boy. I love that show so much; it straddles this incredible line between satire, horror, and sincerity. Especially after dipping my toes in these waters with An Axemas Story, I’d be fascinated to learn how he pulled it off.

How can our readers continue to follow your work online?

You can check out my website at, or I’m on Twitter/TikTok/Instagram as @TheBathYears. I’m also posting tree facts on Instagram as @AnAxemasStory from now to December 17th.

This was very meaningful, thank you so much! We wish you continued success!

Thanks, Savio! Good vibes your way!


  • Savio P. Clemente

    TEDx Speaker, Media Journalist, Board Certified Wellness Coach, Best-Selling Author & Cancer Survivor

    Savio P. Clemente, TEDx speaker and Stage 3 cancer survivor, infuses transformative insights into every article. His journey battling cancer fuels a mission to empower survivors and industry leaders towards living a truly healthy, wealthy, and wise lifestyle. As a Board-Certified Wellness Coach (NBC-HWC, ACC), Savio guides readers to embrace self-discovery and rewrite narratives by loving their inner stranger, as outlined in his acclaimed TEDx talk: "7 Minutes to Wellness: How to Love Your Inner Stranger." Through his best-selling book and impactful work as a media journalist — covering inspirational stories of resilience and exploring wellness trends — Savio has collaborated with notable celebrities and TV personalities, bringing his insights to diverse audiences and touching countless lives. His philosophy, "to know thyself is to heal thyself," resonates in every piece.