Marc Masterson will retire from City Theatre at the end of the current season, leaving the Pittsburgh artistic home where he was the foundation of a groundbreaking trio of co-artistic directors, with Clare Drobot and Monteze Freeland.

Masterson led City Theatre for 20 years before departing in 2000, then returned in 2018, following the departure of Tracy Brigden.
Along with Managing Director James McNeel, Masterson became part of a leadership quartet formed in September 2021, sharing duties in response to a call to action from the racial justice initiative “We See You White American Theater.”
Following Masterson’s retirement on June 30, 2024, Freeland and Drobot will continue in the shared co-artistic director structure, working alongside McNeel as the organization enters its 50th Anniversary next year.
The press release on January 31, 2024, went back to the early days of the South Side theater company, saying, “Masterson’s career is intertwined with the growth of new play production in America over the past 45 years. He started at City Theatre in 1980 and, shortly afterwards, the budget was reduced to zero due to budget cuts. He was able to restructure the organization and the next year, opened a new location in Oakland. With a focus on new American plays the company grew in reputation and attendance.”
Under his leadership, the release said, City Theatre was one of the first in the country to operate on the Small Professional Theatre contract with Actors’ Equity, which allowed union members to work at small- and mid-sized companies for the first time.”
Before leaving City in 2000, to become artistic director at Actors Theatre of Louisville and subsequently South Coast Repertory, Masterson helped City build a national reputation for new works, featuring playwrights including Maria Irene Fornes and Sam Shepard.
The release noted that “Masterson was a leading voice advocating for the inclusion of mid-sized and small arts organizations in the funding structure of the Allegheny Regional Asset District, and he was a co-founder of the Greater Pittsburgh Arts Alliance.” Among his accomplishments was the creation of the Young Playwright’s program at City Theatre, entering its 25th contest and festival in 2024.
Masterson premiered four shows that moved to Broadway, sent dozens to Off-Broadway and created some of the most produced new plays in the country. “He was an early champion of devised work, community-based work, hip-hop theater and of global majority artists.”
After a national search conducted by the board of directors and Management Consultants for the Arts, Masterson returned to City Theatre in July of 2018. In collaboration with McNeel, Masterson oversaw the theater’s producing efforts during the COVID-19 pandemic, including the creation of the Drive-In Arts Festival at Hazelwood Green and digital productions including directing City’s first original digital movie, Claws Out: A Holiday Drag Musical, written by Freeland, Douglas Levine and Shua Potter, that kept artists and staff employed as the industry endured an 18-month shutdown. His recent City directing credits include The Burdens by Matt Schatz (2019), Downstairs by Theresa Rebeck, What the Constitution Means to Me by Heidi Schreck (2023), Native Gardens by Karen Zacarias (2023), and the upcoming Andy Warhol in Iran by Brent Askari, which will close the current season.
Masterson also worked with playwright and screenwriter Kemp Powers (One Night in Miami) in the establishment of the Kemp Powers Fund for Black Playwrights at City Theatre, an initiative that has so far yielded the commissioning of two new plays by emerging Black writers. Additionally, he helped establish a new planned giving program at City Theatre which includes the pledge of the largest one-time estate gift in the organization’s history. An endowment fund in Masterson’s honor was created at City in 2001, and continues to support artistic initiatives for the organization.
“It has been an honor to be part of this extraordinary company and to be able to work with some of the finest theater-makers in the country,” Masterson said in a statement. “I am excited about the future of City Theatre under the leadership of Monteze, Clare and James, and know that along with the staff and board they will make great theater for this community.”
“Marc’s legacy at both City Theatre and in the field at large is deeply felt. Throughout his career he has championed countless new plays and provided support and counsel to artists and arts leaders alike, and I am so fortunate to count myself amongst their ranks,” Drobot said. “City Theatre would not be the institution it is today without his leadership.”
Freeland added, “When I first joined the City Theatre team over a decade ago, the late great Dr. Vernell Lillie urged me to find Marc Masterson. Fifteen years later, not only did I find him, but he also became an instrumental player in my growth as an artist and an arts leader. A constant source of support and ingenuity, Marc has left an indelible mark on City Theatre, the region, and the world of contemporary plays. I am sure (and selfishly hope) this is just intermission before a spectacular next act.”
“Marc’s contributions to City Theatre, our community, and theater field have been tremendous over his decades of tireless service,” said City Theatre Board President David Betts. “The City Theatre Board of Directors is truly grateful for all that he has done and wish him the very best in his well-earned retirement. We look forward to working with Clare, Monteze, and the entire staff team to continue to sustain the artistic impact that City Theatre has had both on the industry and region.”
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