The mostly true story of America's GAYEST founding daddy.
Starring Jenny Zigrino
With Catherine McCafferty, Guy Branum, Beth Stelling & more
The revolution is coming. This time, it's gay.
America is turning 250. Let’s talk about who drilled the men.
It’s 1778. Washington’s army is falling apart. Enter Baron von Steuben: a Prussian immigrant with the expertise to save the Revolution, the ego to demand credit, and enough gayness to found Provincetown himself.
The Drillmaster is the mostly true comedy about America’s gayest founding daddy. He wants a promotion, a little respect, and a farm where he can settle down with his not one, but two lovers. First, he has to teach an army to march and convince a country built by outsiders that he belongs.
Meanwhile, Alexander Hamilton and John Laurens are making “just friends” increasingly difficult to defend. The love letters are real. How you interpret them depends on how horny the historian is.
Military ambition. Romantic incompetence. A founding daddy who deserves his due.
And the question no history textbook dares to ask: does Lin-Manuel Miranda owe gay people reparations?
A sneak peek of the next big thing.
Jenny Zigrino is the Baron. Catherine McCafferty is Washington. Military discipline is already in trouble. Our October 13 developmental reading at The Elysian in Los Angeles has wrapped. Sign up to hear where we’re drilling next.
21+ · General admission · Tickets sold by The Elysian
Who's Who
“The energy, comedic timing, and distinct character voices suggest a piece with significant potential.”
Freaks of HHN
October 13 reading · The Elysian
Sign up for new show alerts
Executive Producer
Art by Levi Hastings
The history is mostly true. The conversations are very real.
Two sold-out developmental readings at The Elysian, Los Angeles.
Revolutionary camp, comedy, and the Elysian reading.
Read review
Caleb, Jenny, and Jeffrey on creating The Drillmaster, the history behind the comedy, and bringing it to the stage.
Inside the SF Eagle reading with Jenny Zigrino and Caleb Zeringue.
Read feature
The Drillmaster’s return to Los Angeles and the October 13 developmental reading.
Read coverage
Jenny on comedy, The Drillmaster, and bringing queer history to the stage.
Read interview Subscription may be requiredThe October 13 Elysian reading appears in the weekly comedy roundup.
Read coverageHear from the people behind the founding daddy.
“Pounding Fathers” with Jenny Zigrino: The Drillmaster, queerness, and the sex lives of colonial America.
Jenny and Caleb talk queer history, theater, and the romance behind the revolution.
Jenny and Caleb join Sports Byline host Rick Tittle for a conversation about comedy.
Caleb on finding his comedic voice, queer representation, and how The Drillmaster began.
Caleb joins Negin Farsad and Jody Avirgan for “Small Shoe Psychological Warfare.”
Caleb on satire, queer history, and taking stories from stand-up to the stage.
Have questions about the show? Get in touch with our team.
With the sweetness of the midwest and the sharp edge of the east coast, Jenny Zigrino brings a powerful comedic performance to any stage. She combines hilarious anecdotes and sharp, witty observations with a cheeky style that challenges social norms and what it means to be human. Her brutal honesty and undeniable charm create a compelling comedic experience you won't forget.
She made her late night debut on Conan with Conan O'Brien and performed a total of three guest appearances. In 2023 she performed on The Late Late Show with James Corden and was met with rave reviews. She was a Just For Laugh's New Faces in 2016 and since then has been featured on Comedy Central, MTV, HBO, Netflix is a Joke and many others. She starred in films such as Bad Santa 2 alongside Billy Bob Thornton and in the horror comedy Too Late in 2021. She's headlined festivals like Moon Tower, New York Comedy Festival, and High Plains Comedy Festival. She's written and performed several comedy specials including Comedy Central Presents the Half Hours and her latest hour special Jen-Z premiered on Comedy Central Digital in 2023. Her latest appearance on After Midnight with Taylor Tomlinson has been hailed as one of the funniest episodes yet by fans. Her most recent Don't Tell Comedy special is out now.
Caleb Zeringue is a stand-up comedian, writer, and producer. He co-wrote Luigi the Musical, served as its original executive producer, and performed in the cast. The sold-out show was covered by The New York Times, CNN, NPR, The Washington Post, and The Hollywood Reporter. It sold over 3,000 tickets across sold-out runs and played Edinburgh Fringe.
As a stand-up, he's a NYC Queer Comedy Festival finalist. He's performed with Don't Tell Comedy and at Cobb's, The Stand, Gotham, and the Hollywood Improv, and he regularly features for Jenny Zigrino (Dropout.TV, Sirius XM). His comedy is queer and southern, with a sharp streak of honesty and a little bless-your-heart still in it.
With Jenny Zigrino, he co-created and co-wrote The Drillmaster, which sold out The Elysian in Los Angeles. It returns there for a staged reading on October 13 and is in development for Off-Broadway. Full credits and booking at calebzeringue.com.
Jeffrey Jay is a Los Angeles-based stand-up comedian and writer from a town so Texas it's called Texas City, Texas. With a Republican judge for a mother and a father who works on oil tankers, he decided life wasn't tough enough and went into comedy.
As a writer, he's a Consulting Producer on The Game Awards, Head Comedy Writer for Feast of Fun, and has worked on Riverdale and Pretty Little Liars. He's been shortlisted by the BBC Writers' Room and advanced in the Warner Bros. Writing Fellowship, Austin Film Festival, and Sundance. In 2025 he was Creative Director of Mary Lynn Rajskub's comedy special Road Gig.
On stage, he's toured the college circuit since 2011, been named one of The Advocate's top transgender comedians, and been featured in The New York Times. He joins Jenny Zigrino and Caleb Zeringue as a writer on The Drillmaster.
Hannah Elsy Productions is a theatre producer and production consultant based in the UK bringing the shows to the stage and beyond. Hannah is also the founder of Superfanbase, an investment platform for the entertainment sector.
Cast
Increase / Woman
Victoria Elena Nones is a comedian, Second City Musical Improv Conservatory graduate, and founder of Women in Comedy. She has performed at The Second City, The Laugh Factory, Sundance Theater Lab, UCB Los Angeles, iO Chicago, and co created a Podcast with the Founder of The Onion. Her work has been featured by The Washington Post, Chicago Tribune, BuzzFeed, ELLE, CBS, NBC, and PBS.
Guy Branum is an Emmy-winning writer and producer whose credits include Hacks, The Other Two, and The Mindy Project. He co-starred in and co-produced Bros, created and hosted Talk Show the Game Show, and wrote the memoir My Life as a Goddess.
Jeremy Crittenden is a New York-based actor, comedian, and producer whose work spans musical theatre, television, and stand-up. He appeared on Broadway in Paradise Square and has performed in Avenue Q and Anne of Green Gables. His screen credits include The Expanse, Good Witch, and Murdoch Mysteries.
Chad Damiani is a Los Angeles clown, writer, and performer. He created the live show and podcast Stand Up and Clown, performs with the international variety show Stamptown, and helped build LA’s contemporary clown scene. His career began as an announcer for World Championship Wrestling.
Emon Elboudwarej is a Los Angeles film and theatre actor. He began studying theatre while pursuing his PhD in epidemiology at UC Berkeley, and has worked with Berkeley Repertory Theatre, California Shakespeare Theater, and American Conservatory Theater.
Leslie Liao is a stand-up comedian, actress, and writer whose comedy draws on life as a single Asian American woman in Los Angeles. She appears in Netflix’s Verified Stand-Up, has performed on The Tonight Show Starring Jimmy Fallon, and was selected for Just for Laughs’ New Faces showcase.
Catherine McCafferty is an actor, stand-up comedian, and writer originally from Chicago, now based between Los Angeles and New York. She hosts Pretty Gay, produced by Sam Reich and Elaine Carroll, appears in Hulu’s Crush, and co-created, wrote, and starred in the web series Bothered. Her solo show (Not) That Bad has played the Edinburgh Fringe.
Beth Stelling is a stand-up comedian, writer, and actress whose specials include Girl Daddy and If You Didn’t Want Me Then. Her television writing credits include Crashing, Rick and Morty, and Strange Planet. She trained in theatre and improv before emerging from Chicago’s stand-up scene.
You're on the list
One more drill: follow the show on Instagram for cast news and updates.
