Penny Jackson: NYC Novelist, Playwright, and Screenwriter 

Penny Jackson is a New York City-based novelist, short story writer, playwright, and screenwriter whose work spans fiction, theater, and film. Her young adult novel Becoming the Butlers was named a best book of the year by the New York Public Library and was optioned for film by Warner Bros. Her short story collection L.A. Child features a Pushcart Prize-winning title story, and her plays have been staged from Off-Broadway to the Edinburgh Fringe Festival in Scotland. She has also adapted her own short stories into two award-winning short films, My Dinner with Schwartzey and Greetings from Sarajevo, screened at festivals on multiple continents worldwide. This guide covers her career, recurring themes, and where to find her published work today. 

Who Is Penny Jackson?

Penny Jackson is a New York City–based novelist, short story writer, playwright, and screenwriter. Rather than settling into a single medium, she has moved fluidly between forms throughout her career, often returning to the same characters, settings, or emotional preoccupations in different shapes. A novel might become raw material for a play; a short story might later be adapted into a short film. This cross-pollination is one of the more distinctive features of her creative practice.

Her professional affiliations reflect that range as well. She has been a resident playwright with New York Madness Theater Company and holds memberships in organizations that span acting, playwriting, and advocacy for women in theater, including the Actor/Directors Unit of the Actors Studio, the Dramatists Guild, the League of Professional Theatre Women, and the International Center of Women Playwrights. Taken together, these affiliations paint a picture of someone deeply embedded in New York’s working theater and literary communities, not a distant celebrity, but a working artist who shows up, collaborates, and stays connected to peer institutions.

Penny Jackson’s Career, Rooted in New York City

Setting matters enormously to Jackson’s work. She has said that her writing consistently returns to teenagers living in New York City, and that even decades removed from her own adolescence, she keeps finding her way back to that vantage point, using contemporary teenage characters as a way of revisiting and reprocessing her own coming-of-age. That instinct, to treat New York not just as a backdrop but as a character in its own right, threads through her fiction, her plays, and her films alike.

This is part of what makes her work feel geographically specific in a way a lot of contemporary YA and literary fiction doesn’t. Her stories don’t just happen to be set in New York; they are shaped by it, by its density, its social stratification, its neighborhoods, and its particular version of adolescence, which looks different from suburban or small-town coming-of-age stories. For readers and audiences who know the city, there’s a texture of recognition in her settings that adds an extra layer of authenticity.

The Novel That Started It: Becoming the Butlers

Jackson’s best-known work of fiction is her novel Becoming the Butlers, published by Bantam Books. The novel was named one of the best young adult books of the year by the New York Public Library, a significant institutional endorsement in a genre where library recognition can meaningfully extend a book’s shelf life and reach. Its critical reception was strong enough that Warner Bros. optioned the novel for film production, a milestone many novelists never reach, regardless of how well-reviewed their work is.

The novel follows a young protagonist, Rachel, whose family is thrown into disarray after her father becomes fixated on the man who left with her mother, to the point of wearing his clothes, using his razor, and eventually moving the man’s own family into their apartment. Rachel’s journey takes her and her father across the ocean to Madrid in search of her mother, a trip that becomes as much about Rachel’s own identity as about finding her. Meanwhile, Rachel becomes captivated by two glamorous, popular siblings, the Butlers, and works her way into their orbit and eventually into their family. Descriptions of the novel characterize it as a compassionate account of a young girl’s search for family, built around the idea that family is ultimately less about blood ties than about a state of mind.

The success of Becoming the Butlers did more than establish Penny Jackson as a novelist to watch, it set a pattern that would recur throughout her career: a story rooted in family rupture and adolescent searching, told with enough emotional precision to attract serious institutional attention, from library honors to studio options.

Penny Jackson’s Short Fiction and the Pushcart Prize

Jackson’s short fiction has appeared in literary magazines across the United States, England, Ireland, and Scotland, an international footprint that’s notable for a writer whose sensibility is so specifically tied to New York. Publications that have carried her short stories include The Pushcart Prize Anthology, The Edinburgh Review, StoryQuarterly, and The Ontario Review, among others, a list that spans well-regarded literary journals on both sides of the Atlantic.

Her short story collection, L.A. Child, published by Untreed Reads, gathers stories about men, women, and teenagers navigating unpredictable lives across a striking geographic range, from London to Boston to Hiroshima to India. The collection’s title story won a Pushcart Prize, one of the most respected honors in American short fiction, awarded annually to outstanding work published in small presses and literary magazines. Winning a Pushcart Prize is the kind of recognition that doesn’t necessarily translate into commercial visibility, but it carries enormous credibility within literary circles, signaling that a writer’s short fiction holds up against the best being published in any given year.

Penny Jackson’s Life in the Theater

If fiction established Penny Jackson’s reputation, theater has arguably become the primary engine of her creative output in recent years. Her plays have moved through a substantial circuit of New York and international venues, from HERE Performing Arts Theater and the Lion Theatre on Theatre Row, to the Edinburgh Fringe Festival in Scotland, to the 14th Street Y and Emerging Artists Theater.

Several of her full-length plays stand out:

• The Battles of Richmond Hill, staged at HERE Performing Arts Theater in 2019, won the Southwest Theater Productions Playwrights Competition in Austin, Texas, and was later published by Next Stage Press. A monologue from the play was also anthologized in an Applause Books collection focused on material for actors over fifty, a detail that speaks to Jackson’s range in writing for characters across the age spectrum, not just teenagers.
• I Know What Boys Want, produced at both the Workshop Theater and the Lion Theatre, was recognized by the theater review site Theater Is Easy and by NYTHEATER.com as one of the best Off-Broadway productions of its year, and was reported as the best-selling play of 2014 for Indie Theater Now.
• Safe won Outstanding Playwright honors at the Planet Connections Theatre Festivity, and went on to be produced at the Edinburgh Fringe Festival and at 59E59 Theaters as part of the East to Edinburgh Festival, a rare trans-Atlantic production trajectory for an independent play.
• Louise in Charlestown, a full-length solo show, was produced at the Hudson Theaters in Los Angeles and at the United Solo Festival in New York, one of the largest solo theater festivals in the world.

Jackson’s shorter, one-act work has been similarly prolific. Plays like Directions, Phoenix, A Different Place, A Gift from the Memorial Shop, The Glorious Gloria, and Before have been produced at venues including Nylon Fusion Theater, Emerging Artists Theater, the Kraine Theater as part of the FRIGID Festival, and the Atlantic Theater. Before is a particularly notable entry: it won first prize in a gun control–themed play competition sponsored by the University of Illinois–Urbana, was featured in Necessary Exposure, an exhibit at Dixon Place Theater spotlighting female playwrights, and was later selected by Applause Theatre as one of the best American short plays of its year. It’s a reminder that Jackson’s work isn’t limited to coming-of-age family drama; she’s also engaged directly with charged social and political subject matter.

Penny Jackson: From the Page to the Screen

In the last several years, Penny Jackson has extended her storytelling into short film, adapting two of her own published short stories into award-winning films: My Dinner with Schwartzey and Greetings from Sarajevo.

My Dinner with Schwartzey premiered at the Bermuda International Film Festival, an Oscar-qualifying festival, in 2019. From there, it built an unusually broad festival footprint, screening in England, Mexico, Sweden, Italy, Japan, Australia, France, Canada, and multiple U.S. cities including Austin, Marina del Rey, Fort Worth, and Las Vegas. The film accumulated more than thirty award nominations and roughly two dozen wins, including top honors at the French International Film Festival, the Manhattan Film Festival, the NYC TV and Film Festival, the Long Island International Film Festival, and the Top Indie Awards.

Greetings from Sarajevo, adapted from Jackson’s play Directions (which itself premiered at Nylon Fusion Theater in 2012), had its world premiere at the YoFi Festival in Yonkers in November 2020. It has since won several honors, including multiple awards for its screenplay, along with recognitions for acting, cinematography, editing, musical score, production design, and sound from outlets like the Southern Shorts Awards.

What’s notable about this stage of Jackson’s career is the pattern of adaptation and reuse: a short story becomes a play, a play becomes a short film, and each version finds its own audience and its own set of accolades. It’s an efficient, almost sustainable model for a working writer, one that treats a strong story not as a single-use asset but as raw material that can be reshaped for different mediums and different rooms full of people.

Recurring Themes in Penny Jackson’s Work: Family, Identity, and Reinvention

Across novels, short stories, plays, and films, a few threads recur consistently in Penny Jackson’s work:

Family as something chosen, not just given. From Becoming the Butlers, where a teenage girl works her way into another family entirely, to the domestic upheaval at the heart of that same novel’s plot, Jackson repeatedly explores how people construct family bonds outside of strict bloodlines, and how fragile or improvised those bonds can be.

Adolescence revisited from adulthood. Jackson has been candid that her fascination with teenage characters is inseparable from her own process of revisiting her adolescence. Even her most contemporary teenage characters function, in part, as vehicles for her own retrospection, which may explain why her depictions of teenage longing and social maneuvering feel emotionally specific rather than generic.

Displacement and searching across geography. Whether it’s Rachel and her father traveling to Madrid, or the international scope of L.A. Child’s stories spanning London, Boston, Hiroshima, and India, Jackson’s characters are frequently in motion, searching for someone or something across unfamiliar geography.

Social and political engagement. Plays like Before, which grew out of a gun-control-themed competition, show that Jackson’s interests extend beyond interpersonal and family drama into more overtly political territory, without abandoning the character-driven approach that defines her other work.

What Jackson’s Career Suggests About Building a Creative Life

For writers, playwrights, and filmmakers trying to figure out how to sustain a career without mainstream fame, Penny Jackson’s trajectory offers a few instructive patterns.

First, there’s the value of institutional validation over viral visibility. A New York Public Library best of the year honor, a Pushcart Prize, an Edinburgh Fringe production, a Warner Bros. option- none of these guarantee household-name status, but together they build a body of credibility that opens doors, attracts collaborators, and sustains a decades-long career.

Second, there’s the discipline of working across mediums without losing a throughline. Jackson doesn’t pivot from fiction to theater to film as separate, disconnected pursuits; she treats them as different lenses on the same recurring preoccupations: family, adolescence, displacement. That consistency likely makes it easier for audiences, critics, and producers to recognize her voice regardless of the format.

Third, her career underscores the importance of place. By staying rooted in New York City’s literary and theater scenes, while still sending work out to international magazines, festivals, and competitions, she has built a career that is locally grounded but not provincial.

Where to Find Her Work

Readers interested in Jackson’s fiction can find Becoming the Butlers and her short story collection L.A. Child through major retailers and her publishers’ pages. Theatergoers in New York and beyond can keep an eye on productions from companies she’s worked with, including New York Madness Theater Company, and watch for restagings of works like The Battles of Richmond Hill, I Know What Boys Want, and Safe. Her short films, My Dinner with Schwartzey and Greetings from Sarajevo, continue to make the rounds on the festival circuit, so film festival programs remain a good place to catch them.

Conclusion

Penny Jackson’s career is a reminder that a creative life doesn’t have to be built around a single breakout hit or a single medium. It can be built, instead, through steady, cumulative work: a novel that earns a library honor and a studio option, a short story that wins a national prize, a play that travels from an Off-Broadway stage to the Edinburgh Fringe, a short film that collects two dozen festival awards on its way around the world. Few writers manage to sustain output across fiction, theater, and film simultaneously, and fewer still manage to do it while keeping a consistent emotional and thematic voice. Penny Jackson has done both, quietly, persistently, and almost entirely on her own terms, working out of the city that keeps showing up as the true setting of everything she writes.

Frequently Asked Questions