City Theatre Announces Season Directors and Artistic Department Restructuring

City Theatre Company, Pittsburgh’s home for contemporary plays located on the South Side, has just announced the directors for its 2025/2026 season as well as changes
to the artistic department structure.

In the fall of 2021, City Theatre announced a new shared leadership model, promoting artistic staff Clare Drobot and Monteze Freeland to co-lead the organization alongside
artistic director Marc Masterson and managing director, James McNeel. After Masterson
retired in 2024, Drobot and Freeland shared the Co-Artistic Director title for the 2024/25
season. With Freeland moving on from City Theatre to serve as Artistic Director at
Alumni Theater Company in May, the board of directors has voted to make Drobot
the sole Artistic Director of City Theatre, leading alongside Managing Director James McNeel.

“There is no greater champion for new plays in Pittsburgh than Clare Drobot,” said Board President Barbara Rudiak, “and we are thrilled to appoint her to serve as Artistic Director. Clare is a tireless advocate for playwrights, intentional and meaningful community engagement, equity on and off stage, and for ensuring that theater is not only relevant but evolving to meet this changing world. Some of City Theatre’s most daring and ambitious projects – from originating F**k7thGrade by Jill Sobule and Liza Birkenmeier to this season’s Another Kind of Silence – are a result of her tireless efforts and vision.”

A trained dramaturg, Drobot joined City Theatre in 2015 as Director of New Play Development. Prior to being appointed as Co-Artistic Director, she also served as Associate Artistic Director to Masterson. In addition to her new play development work through commissions, productions, and the Momentum Festival, Clare was integral to the creation and implementation of the organization’s City Connects community engagement initiative, which was created in early 2017 and has featured partnerships with over 120
nonprofit organizations. Rounding out the artistic department this season to work with Drobot (and longtime Director of Education and Accessibility Katie Trupiano) is Artistic Associate Melva Graham and freelance Associate Producer Miso Wei.

“It’s an honor to continue to collaborate with James, the staff, and board to champion and shape City Theatre’s artistic vision. I’m deeply grateful to Monteze and Marc for our work together and can’t wait to introduce audiences to these vibrant theatrical worlds,” Drobot shared. “The six dynamic artists—four of whom call Pittsburgh home—at the helm of these productions are leaders in the field. Get ready for an electrifying season with three world premieres, a hit Broadway comedy, and a reinvestigation of one of City Theatre’s most iconic titles.”

Furthermore, City Theatre is officially announcing the directors for the 2025/2026 season, featuring an eclectic mix of first-time and returning artists to the organization. Building on recent collaborations with Carnegie Mellon University’s School of Drama, five season directors are on faculty at CMU.

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