Anya Kai, reporting

In the landscape of American theater, few names carry the historical gravity of Reginald T. Jackson. Often hailed as a “titan of the New York stage,” Jackson’s career is a masterclass in artistic bravery. In 1988, at the height of the AIDS crisis, he founded the Rainbow Repertory Theatre, the nation’s first Black Gay Theater—a feat he jokingly describes as “ballsy,” but one that fundamentally shifted the trajectory of queer storytelling.

As he prepares to debut his new comedy, When We Practice to Deceive, at the 2026 Fresh Fruit Festival, Jackson remains as sharp, structured, and subversive as ever.

The Comedy of Truth: Disarming the Audience

Jackson has long understood a fundamental theatrical secret: if you want to change a mind, you first have to open a mouth with laughter. His new play centers on a “bathroom revelation”—the moment a future mother-in-law discovers the lead character, Lady Jasmine, is a trans woman.

“Humor disarms your audience,” Jackson explains. “It gives you a clean slate to talk to them and make your case. Jesters are usually the wisest persons on stage!” By utilizing the high-stakes, high-decorum setting of an expensive restaurant, Jackson heightens the tension. The formality of the environment ensures that the revelation remains a quiet, private standoff rather than a public spectacle, mirroring the way our most profound personal tragedies often unfold in hushed tones behind polished tables.

A Love Letter to the Trans Community

While the play is a comedy, its roots are planted in a sobering modern reality. Jackson notes that while “regular” Black gay men and women have become more integrated into the cultural fabric, the trans community remains under siege.

Jackson cites the American Medical Association’s classification of violence against trans women as a “full-blown epidemic” as a primary motivation for this script. “I was compelled to write a positive story that shows trans women in the real light of day. This play is a love letter to the trans community.”

In the play, the “deception” used by Lady Jasmine is framed not as malice, but as a survival tactic—one she eventually outgrows as she learns that “chosen family” can be more enduring than blood.

The Architecture of a “Bulletproof” Script

Jackson’s writing isn’t just inspired; it is engineered. Named a National Shakespeare Pioneer by the legendary Joseph Papp, Jackson credits his classical background for his contemporary success.

“I am a very strict writer when it comes to structure,” he says. “I have borrowed from Shakespeare, Chekhov, and Tennessee Williams.” This commitment to a solid foundation is what he taught for 15 years in the NYC school system through his curriculum, Writing on Your Feet!. By transcribing the first drafts of young students and showing them their own words on the page, he helped a generation find their voices while keeping his own perspective fresh and connected to Gen Z’s progressive energy.

Forty Years of “Pushing the Envelope”

Jackson notes with a touch of wit that while his definition of “truth” hasn’t changed in four decades, the public is finally catching up to him.

• The 1980s: He turned King Lear into a Black gay drag queen dying of AIDS in House of Lear.
• The 1990s: He explored the “down low” phenomenon in Straight Boys and put Ball Culture on stage in 1994—decades before it became a mainstream television staple.
• The 2020s: He watches as shows like A Strange Loop and Cats: The Jellicle Ball bring the Black queer experience to Broadway, doors he helped kick open forty years ago.

The Intimacy of The Wild Project

For the run of When We Practice to Deceive (April 23-25), Jackson is relishing the chance to work in the intimate confines of The Wild Project. Having worked on massive stages like The Public, he finds a unique power in being “right in the face” of the audience.

“I want a dialogue,” Jackson asserts. “I do not let them off the hook. We are going to bring the story right to you and drop it on your lap.”

The Final Revelation

As the Fresh Fruit Festival celebrates the evolution of queer storytelling, Jackson’s goal remains focused on the individual. He wants every audience member to leave the theater understanding the imperative of living authentically, regardless of the cost.

“Meet people where they are,” he challenges, “but challenge them to expand their minds and hearts to include things they do not yet understand but know is right.”

Tickets available at https://events.ticketleap.com/events/alloutarts