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Prolific Portland playwright Kevin O’Leary has found inspiration in everything from classic literature to recent politics. He’s written 25 plays in 36 years and he’s far from finished.

O’Leary’s latest creation, “Alice’s Threshold,” was inspired by his own “feeling of dread upon seeing the plight of all the homeless in my hometown.” It will have its premiere run from Sept. 30 to Oct. 10 at Coffee by Design in Portland.  

Playwright Kevin O’Leary. (Photo by Tiki Fuhro)

The drama tackles the thorny issue of the city’s unhoused population by highlighting the dire condition of a single mother living on park benches in Portland’s Deering Oaks. In his efforts to respectfully “get it right” about the issue, O’Leary researched the subject by interviewing several professionals involved in addressing such problems. 

A cast of three will include familiar faces from the local theater scene.

Over the years, Marie Stewart Harmon has become the one performer O’Leary refers to as “the chief interpreter of my words.” She studied under and later worked with the author since her high school days and, in an interview, expressed admiration for O’Leary’s passion to create good theater. Though she notes that the author can sometimes appear to be a bit of an eccentric, she feels lucky to have received the “gift” of roles written for her by him.

Harmon views her character Alice as “a very strong, stubborn, defiant and loving woman” facing difficult circumstances. She said she learned about the nature of Alice’s plight through her own research, as well as O’Leary’s, and is enthusiastic about working again with two of her favorite actors.

Marie Stewart Harmon as Alice Fromier in the world premiere of Kevin O’Leary’s “Alice’s Threshold.” (Photo by Kat Moraros Photography)

 Sean Ramey, whom O’Leary describes as “brilliant,” will fill the role of a sympathetic but nonetheless by-the-book judge. This will be the sixth O’Leary play in which he has performed.

Tyler Costigan, in his second O’Leary role, will play Alice’s well-intentioned but inexperienced case manager.

James Hoban, better known to many Mainers for his acting, will direct this new play, his second time helming one of O’Leary’s plays. He said he admires O’Leary for his bravery and willingness to take on difficult issues with an enduring sense of “humor, heart, and empathy.” Hoban asserts that “theater needs to be less observational and more conversational” to create “a better understanding of things we might rather avoid.” 

Both the author and director expressed gratitude to Coffee by Design for the use of their space. Hoban described it as having an “industrial feel and rough edges” that should fit the play well. Harmon went so far as to call it a “guerrilla space.”

O’Leary, Hoban and Harmon said they hope the play will suggest more constructive involvement and less indifferent avoidance to the audience when they encounter people who are unhoused among us. 

Steve Feeney is a freelance writer who lives in Portland.

From left, Tyler Costigan, Marie Stewart Harmon and Sean Ramey in “Alice’s Threshold.” (Photo by Kat Moraros Photography)

“Alice’s Threshold,” a play by Kevin O’Leary, will be performed Sept. 30-Oct. 10 at Coffee By Design, 1 Diamond St., Portland. Ages 16+. Tickets $25. To purchase tickets, go to eventbrite.com.