All the School's a stage.

"On the Town." "Grease." "Cabaret." "Fools." "Damn Yankees." "The Sound of Music." "Much Ado about Nothing." "Tartufe." "Spamalot." "Nice Work If You Can Get It." Theatre thrives at Gilman. Through dramatics, students forge a shared sense of purpose and become an indissoluble team as they work together to mount a production. Theatre is about much more than just story telling; and, it is also about much more than a celebration of the self and one's own abilities. To paraphrase Sophocles, dramatics reflects a spirit moving through a community, both in the audience and onstage, a shared sense of understanding and experience, and an unparalleled unity.

During the course of the school year, the tri-school community produces five plays at the Upper School level—two at Gilman, two at RPCS, and one at Bryn Mawr, not including student directed plays. Middle School thespians mount two productions annually, and even Lower School boys get into the act with myriad class plays each year. Whether on the stage or behind, each performer, musician, or stagehand shares the spotlight.

Class plays give young boys a creative outlet to share information through dramatic storytelling.

The Middle School offers boys the opportunity to act in two annual theatrical productions.

Gilman’s 2015 “Nice Work If You Can Get It” was the show's first production in the state of Maryland, and one of very first high school performances in the country.