Aaron Jackson Brings Wit and Heart to “Messy White Gays” Off-Broadway

Aaron Jackson’s career has been defined by fearless comedic performances and a commitment to authentic LGBTQ+ storytelling. As he steps into the role of Caden in Drew Droege’s new Off-Broadway comedy, "Messy White Gays", Jackson brings his signature wit and emotional range to a production that promises both outrageous humor and pointed social commentary .

Jackson’s journey as a performer began in New York City, where he quickly established himself in the city’s vibrant comedy and cabaret scene. Known for his improvisational prowess and sharp comedic timing, Jackson gained wider recognition as a member of the celebrated sketch group “The Upright Citizens Brigade” and for his work with “Baby Wants Candy,” a long-running musical improv troupe.

His solo show, "The Teddy Teddy Show", was performed at both the NYC International Fringe Festival and the Hollywood Fringe Festival, where it received praise for its inventive storytelling and Jackson’s dynamic stage presence .

Jackson’s recent breakout role came in the cult-favorite film "Dicks: The Musical", where his comedic energy and thoughtful approach to queer representation helped the movie become a festival hit and a touchstone for LGBTQ+ audiences . The film’s irreverent style and boundary-pushing humor aligned closely with Jackson’s artistic ethos, marking him as a sought-after comedic talent in both stage and screen projects.

In addition to his work as an actor, Jackson recently published his debut novel, "The Astonishing Life of August March". The book, praised for its wit, heart, and nuanced exploration of outsider identity, further showcases Jackson’s versatility as a storyteller and his commitment to centering queer voices.

In "Messy White Gays", Jackson plays Caden, one half of a couple navigating the chaotic aftermath of a murder—just as friends arrive for brunch in Hell’s Kitchen. The play, written by Drew Droege and directed by Mike Donahue, is a biting satire of privilege, identity, and relationships among gay men. Jackson’s performance is anticipated as both hilarious and deeply resonant for LGBTQ+ audiences, who see themselves reflected in the show’s messy, complicated characters .

Jackson joins an all-star cast, including Tony Award nominee James Cusati-Moyer and Zane Phillips, contributing to a production that is already generating buzz within New York’s theatre community for its unapologetically queer perspective and sharp comedic edge .

Throughout his career, Jackson has prioritized projects that affirm LGBTQ+ identities and challenge stereotypes. His work on stage and screen is noted for its inclusivity, humor, and emotional honesty. By embracing roles that reflect the lived experiences of gay men and the broader LGBTQ+ community, Jackson has contributed meaningfully to the ongoing evolution of queer representation in American theatre .

Jackson’s visibility as an artist and storyteller helps foster empathy, understanding, and joy—qualities that imbue both his performances and his writing. As "Messy White Gays" prepares for its Off-Broadway debut, Jackson’s role stands as a testament to the power of queer performers to redefine mainstream narratives and celebrate the complexity of LGBTQ+ lives.

Audiences can catch Jackson’s performance when "Messy White Gays" opens at the Duke on 42nd Street in October 2025—a production that promises both laughter and thought-provoking insight into the messy realities of queer life in New York City .