Caitlin Saylor Stephens

Roberta, a visionary fashion photographer, lands the gig of a lifetime - the cover of Vogue - but quickly learns it could be her downfall. Location is a nightmare. The models are vicious. Hair and makeup is MIA. And the cigarette supply is running dangerously low. As chaos escalates, Roberta must summon her strength and find the perfect light to capture a moment of beauty in a brutal world. Set against the backdrop of a crumbling European estate in the aftermath of Princess Diana’s wedding, Five Models in Ruins, 1981 is a darkly comedic exploration of a woman grappling with the power of her own gaze.

Never before has C, a single 30-something woman, asked her father for anything. Let alone a Christmas gift. But this year is different. After finally gaining the courage to ask her father for what she really wants; a chef’s knife, his refusal to meet her desire inspires becomes the final cut in a long history of paternal wounds, propelling C to sever ties, not just with him, but with every man who’s hurt her. A darkly funny and cutting play about longing, denial, and how capitalism refracts our deepest psychological needs through the things we think we want.

After an accident in their West Village apartment, Nick and Sylvie retreat to a hotel room in a nearby members-only club. Desires collide inside the room as Sylvie, career-driven and ambitious, prepares for a big day ahead while her stoner boyfriend Nick revs up for a wild night out. Modern Swimwear is a provocative new play by Caitlin Saylor Stephens about swimwear designer Sylvie Cachay's life. And the cost of female ambition.

Set in the fluorescent hellscape of an American Apparel store, When We Went Electronic follows two retail workers—Brittany and Bethany—spiraling through a shift as they attempt to piece together the events of the wild night before. Desperate to remember, they resort to electrocuting themselves in an effort to shock their brutal truth out. As their memories blur, contradict, and collapse, the violence of their corporately-controlled lives begins to surface. Darkly comedic and brutally rhythmic, When We Went Electronic is a feminist critique of memory, trauma, and the seductive trap of consumer culture. With pop music and razor-sharp dialogue, the play explores what it means to be seen, exploited, and erased in a world that profits off women’s bodies—and their breakdowns.

After weeks of being trailed by a mysterious car, Ros, a fertile 20-something, finally accepts an invitation to step inside. Once buckled in, the car’s owner—a former video girl-turned-mystic—offers her a haunting proposition: power in exchange for her fertility. As the SUV hurtles across the country toward Omaha, flanked by angels, the women embark on a surreal, high-gloss journey through luxury, longing, and the psychic toll of womanhood under capitalism. Set inside the plush, masculine interior of a moving vehicle, Black Escalade is a darkly mythic road play about speed, sacrifice, and what it costs to belong to your own body.

When C, an independent, cosmopolitan 30-something woman receives a graphic video from her uncle's husband, she’s thrust into an emotional and moral tailspin. Should she stay silent to preserve family peace? Or speak up and risk blowing apart the image of the so-called-progressive family she grew up in? As fallout ensues, C is forced to confront the limits of her own liberal values–and the uncomfortable gap between theory and lived experience. A Picture of the Dog is a volatile, intimate, bitingly funny exploration of power, complicity, and what it means to take a stand during a digital snafu when the perpetrator is close, beloved–and not even straight.

As a global pandemic rages on, Jessica—a single, thirty-something woman—spirals into obsession after the loss of her former flame: her married, middle-aged boss. Desperate to stay connected, she sinks into a bottomless pit of cyberstalking—Zillow, Instagram Stories, criminal record checks. Refresh. Refresh. Refresh.Consumed by her digital addiction, Jessica finally hits rock bottom and realizes the real problem isn’t him—or even her. It’s the internet. Determined to destroy the thing that destroyed her, she hires a genius hacker named Miles to help her take it down. For good. What follows is a surreal, darkly funny quest to unplug from the matrix and rediscover the beauty of living in a world offline.

When Liv meets Pete, a sex-positive, ethically non-monogamous, feminist union organizer, Liv falls head-over-chemically-attracted. But when Petes's violent behavior, misogynistic gospel, and angry social media posts begin contradicting his woke identifiers, Liv starts to question the meaning of language itself. Or if she's just imagining things. A new play about the ethics of love and the red flags we ignore when we're overcome by loneliness.

After a long separation, two mountain lovers reunite for one hot n’ heavy night in a broke-ass bar. But when Oprah-obsessed Joley reveals the scars of a brutal domestic attack, the reunion twists into a reckoning. Now faced with their shared past, a violent present, and one very real corpse, the two must confront their guilt, unearth buried truths, and figure out how the hell to forgive—before the night buries them, too.

On the graveyard shift at a health insurance call center, there’s nothing left to do but get high, get honest, and try to stitch together what’s left of the broken American healthcare system. As the night drags on, cubicle walls collapse, secrets surface, and the workers begin to wonder: who are we really saving—and at what cost? Company Happy Hour is a brutal comedy inspired by the writer’s own experience answering phones at a health insurance company during the Obamacare era.

After a tragic accident in the starting gate, a world-class jockey meets the horse of his dreams in the ICU. A great love is born.

On the eve of his bachelor party, Mike and his best man Greg find themselves at the bottom of the Hudson River beneath an overturned canoe. The two men embark on an underwater adventure to find their friend, Alex, an excellent swimmer, while the bride perfects her look for the big day. Who and what is missing on this fateful night and will their lives ever be the same?

After working as a webcam girl for over a decade, Rina finally purchases a basic economy ticket to Moscow. But on the eve of her journey, her town is hit by a snowstorm, and she and her two sisters must reckon with their truest loves and greatest obsessions in the snowy Siberian landscape. Maybe they'll eventually dig out the car.

After discovering a hidden television in the basement, Jonbenet Ramsey unearths the mystery of her murder, twenty years after her death.