Theater Alliance Announces 21st Season


Final Season Under Leadership of Producing Artistic Director Raymond O. Caldwell
Centers Community, Journeys, and Homecoming

(Washington DC) The upcoming 2023-2024 Season from Theater Alliance will explore movements — both how we move through space and how we change the world. 

Starting small, with the walk home from middle school in the Kennedy Center’s performance run of co-production Look Both Ways: A Tale Told in Ten Blocks, the season will build with Holly Bass’s Trans-Atlantic Time Traveling Company, which explores the parameters of freedom from both history and modernity. The third and final production, which will be announced later in the fall, will speak to social, political, and philosophical movements as it travels through a regional tour, in addition to a performance run at the Anacostia Playhouse. 

And these movements come at a particularly resonant time: After leading the award-winning socially-conscious theater as Producing Artistic Director since 2019, Raymond O. Caldwell will step down at the end of the new season. 

“Theater Alliance has long held the philosophy of ‘make it better for the next generation,’” says Caldwell. “Over the past years, the staff and I have worked to build the company. Now it’s time to make space for a new artistic leader.” 

Caldwell, who has recently directed shows at Signature Theatre, Round House Theatre, Olney Theatre Center, and Mosaic Theatre Company, says he plans to devote his time to directing — both in the DC area and nationally. 

“Nothing will change my love for Washington, DC,” he says. “I am wholly committed to this city, its community of artists, and the extraordinary design, performances,  and new play development that happens in the District.” 

Throughout his time at Theater Alliance, Caldwell has bolstered the mission and accomplishments of the company, earning Helen Hayes Awards for productions including Blood at the Root (Outstanding Production, Outstanding Ensemble, Outstanding Direction, Outstanding Choreography, Outstanding Lighting/Projections, Outstanding Sound Design, and Outstanding Lead Performer) in 2019 and Poetry for the People: The June Jordan Experience (Charles MacArthur Award for Outstanding Original Play Adaptation) in 2022. Theater Alliance has raised its national profile in this time, earning support from the National Endowment for the Arts and becoming a core member of the National New Play Network. 

Caldwell says that he is proud of what Theater Alliance has accomplished during his tenure, citing the collaborative efforts of the board, staff, and artists as crucial to his success.  

Recently lauded by City Paper as “Best Theatrical Innovator,” Caldwell was one of the first arts leaders in the region to pivot to digital theatermaking in 2020, when live theater was impossible, centering DC playwrights and performers in a season of new work developed to meet the needs of unprecedented circumstances. 

Last year, in partnership with the U.S. Department of State, Caldwell led an Arts Envoy from Theater Alliance to Kolkata, India, where a cohort of international artists gathered to discuss themes of inclusion, diversity, equity, and accessibility (I.D.E.A.) and create a new work of theater to help audiences and their communities throughout India address these topics. Once back in Washington, DC, a similar program brought students from local colleges and universities together to engage in similar work. The resulting play toured several area campuses last spring.  

Building community has been a throughline at Theater Alliance, and Caldwell has invested deeply in both the geographic community near the Anacostia Playhouse as well as our city’s rich community of theater artists. His community-driven initiatives have included organizational partnerships with Howard University, the Wendt Center for Loss and Healing, Black Swan Academy, Whitman-Walker Health, and more. Currently, Look Both Ways: A Tale Told in Ten Blocks, which Caldwell directed and co-adapted with El Chelito, is enjoying a performance run that progresses from the Anacostia Playhouse this month to the John F. Kennedy Center for the Performing Arts in October, and will go on tour next year. 

The company is conducting a search for the next artistic leader, who will be announced by the end of this calendar year. Caldwell will remain with the organization through the end of the theater season, concluding in June 2024. 


Look Both Ways: A Tale Told in Ten Blocks 
(Kennedy Center Performance Run) 
October 14 – 29, 2023
Adapted by El Chelito and Raymond O. Caldwell 
From the book by Jason Reynolds
Directed by Raymond O. Caldwell
A Co-Production with the John F. Kennedy Center for the Performing Arts 

This story was going to begin like all the best stories. With a school bus falling from the sky. But no one saw it happen. They were all too busy— Talking about boogers. Stealing pocket change. Skateboarding. Wiping out. Braving up. Executing complicated handshakes. Planning an escape. Making jokes. Lotioning up. Finding comfort. But mostly, too busy walking home.

Through these ten stories, National Book Award finalist and New York Times bestselling author Jason Reynolds offers glimpses into the private struggles, strengths, and secrets of students who only know each other in passing. Best enjoyed by ages 8+. 

The Trans-Atlantic Time Traveling Company
Feb. 27 – March 17, 2024
Developed by Holly Bass

Three freedwomen travel through the American south in the 1860s with a medicine show, but unlike other snake oil salesmen of the day, these mysterious women give away their healing potions in an attempt to cure a dangerous disease that threatens to destroy future generations. A devised work of dance theater, The Trans-Atlantic Time Traveling Company combines vaudeville, sampling culture and time travel to engage the audience in a conversation about what it means to be free and ways we can move towards an equitable and just society.

Surprise Final Production
Summer 2024
Directed by Raymond O. Caldwell 

To be announced in conjunction with news of the incoming Producing Artistic Director later this fall. 


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Theater Alliance develops, produces, and presents socially conscious, thought-provoking work that fully engages our community in active dialogue. As the resident theater company of the Anacostia Playhouse since 2013, Theater Alliance is proud to produce professional, award-winning work in Anacostia about social and cultural topics. Through our work, Theater Alliance hopes to create an audience laboratory where the myriad perspectives of DC are face-to-face, confronting issues and tackling difficult questions that affect our diverse community.

Locally, Theater Alliance has twice been finalists for the Mayor’s Art Award, featured in the Greater Washington Catalogue for Philanthropy, received the Capitol Hill Community Foundation’s Keller Award for making significant, ongoing contributions to the life of the community, and awarded two DC Commission on the Arts and Humanities’ UPSTART Grants for capacity building. Nationally, we have received the American Theatre Wing’s National Theater Company Grant, an NEA Art Works grant, and is a proud Core Member of the National New Play Network. Theater Alliance has received 90 Helen Hayes Award Nominations and 20 Helen Hayes Awards.