Charlie O'Leary



“In 2007, when I was a closeted fifteen-year-old, I had a minor brush with YouTube fame.” A multimedia solo performance about how we cringe at our past selves.




Charlie O’Leary is an alumnus of the Project Y Playwrights Group, the Brooklyn Generator, the Advanced BMI Workshop, Crashbox Theatre Company’s Write Play Launch, the 24 Hour Plays: Nationals, and the Fornés Playwriting Workshop. He has been a finalist for the Seven Devils Playwrights Conference, the DVRF Playwrights Program, Sanguine Theatre Company’s Project Playwright, and the Woodward/Newman Drama Award; a three-time semifinalist for the O’Neill National Playwrights Conference; and 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 West End Lounge, and the Duplex. His short works have been published by Methuen Drama and Theatre Now New York. He is currently pursuing his MFA at Iowa Playwrights Workshop.



1. When did you start writing plays? If you had a moment where you realized you wanted to write, what was it?


In high school, I spent hours playing, writing, and designing chaotic fiction, or ARGS – interactive, community-based, 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, via a live event in Boston, which at age 16 I sold my parents as a college visit. ARGs sparked my interest in storytelling and performance, but it wasn’t until I took a playwriting course with Anne García-Romero my sophomore year of college that I realized I wanted to write plays.


2. How did you come to write your OOB play? Was there a particular inspiration behind its creation? How has it developed?


In 2014, I was invited by my friend Alice Roth to participate in her event “Bullsh*t Olympics,” which featured artists sharing their pretentious, embarrassing, and generally bullsh*tty work from days gone by. The “work” I presented was from the mortifying YouTube vlog channel I ran in high school; I combed through my videos and picked the best (worst) soundbites, along with some choice comments, and read them aloud in a tiny art gallery in SoHo. The experience was weirdly cathartic, so I continued developing the piece: first into a three-character short play (presented by Project Y Theatre in 2015), then into a solo work with audience participation. The most recent iteration of the play, containing multimedia elements, was developed last year in Meredith Alexander’s Performing Autobiography course at the University of Iowa, where I’m currently pursuing my MFA.


3. What are 5 words that describe who you are as a playwright?


Dark comedy. Productive discomfort. Metatheatre.


4. What/who are some of the major influences on your writing?


I am influenced by non-theatrical work – ARGs, video games, anime, journalism, music – but most especially I am inspired by the work of other playwrights, particularly those I’ve been lucky enough to get to know as colleagues and friends. Among many many (many many) others, I owe an enormous debt to the playwrights Bixby Elliot, Anne Garcia-Romero, Ken Greller, and Lia Romeo, all of whom have served as mentors to me in this field.


5. What’s one fact someone would never guess about you?


No one would ever guess that I’m turning thirty this year! Would they? Would they?!


6. What are some of your favorite plays?


Oh, this is an impossible question! I’m just going to type up the first 25 amazing plays I can think of, and I’ll kick myself later for all the ones I forgot:

The Antipodes by Annie Baker, Bright Half Life by Tanya Barfield, I’ll Never Love Again by Clare Barron, Indeed, Friend! by Eliza Bent, Revolt. She Said. Revolt Again. by Alice Birch, A Life by Adam Bock, Paris by Eboni Booth, Caught by Christopher Chen, Jacuzzi by The Debate Society, Fairview by Jackie Sibblies Drury, The Tomb of King Tot by Olivia Dufault, Fefu and Her Friends by Maria Irene Fornes, What to Send Up When It Goes Down by Aleshea Harris, Mary Jane by Amy Herzog, A Bright New Boise by Samuel Hunter, Gloria by Branden Jacobs-Jenkins, Locusts Have No King by C. Julian Jiménez, Brahman/i by Aditi Kapil, Mrs. Murray’s Menagerie by The Mad Ones, The Evening by Richard Maxwell, Bootycandy by Robert O’Hara, Peerless by Jiehae Park, Mala Hierba by Tanya Saracho, What the Constitution Means to Me by Heidi Schreck, Tom & Eliza by Celine Song

In writing this list I avoided naming things I’ve worked on as a producer or actor or dramaturg – some favorites there include She by Renee Roden, If on a Winter’s Night by Bixby Elliot, and The Last Tiger in Haiti by Jeff Augustin – but now I’ve named 28 plays and you were probably just looking for three or four – I’m so sorry! – I just really love plays!


7. Any new projects you’re working on or shameless plugs?


Most recently, I adapted my full-length solo play “The Switch” into an audio drama, directed by Ivey Lowe and released by the Fresh Fruit Festival this May.