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As a performer, playwright, producer, director and artistic director, Monteze Freeland has for years been among the busier folks on the local theater scene.

But Freeland’s current job, as artistic director at Alumni Theater Company, brings him full circle in some sense to his earliest days in theater, back before he even came to Pittsburgh — even as Alumni wraps its season with a production of the hit musical “Once On This Island,” Friday, July 31, to Sunday, Aug. 2, at Oakland’s Charity Randall Theater.

Freeland grew up in Baltimore, where from ages 10 to 18 he trained and performed with The Arena Players, the nation’s oldest continuously operating Black community theater (founded in 1953).

He graduated from Point Park University and embarked on a career that, though long centered at Pittsburgh’s City Theatre, touched a wide swath of troupes and stages.

Freeland has been a key contributor at Mark Clayton Southers’ Pittsburgh Playwrights Theatre Co., where he’s artistic producer and curator of its current season. In 2021, the debut of Freeland and composer Michael Meketa III’s “Kalopsia: The Musical” was the first in-person show at the New Hazlett Theater since the pandemic began.

The same year, Freeland became a co-artistic director at City, where he’d direct shows like the 2024 hit “Fat Ham.” And just this year, he played the lead in Pittsburgh Public Theater’s production of “Primary Trust,” that venerable troupe’s final mainstage show before its imminent merger with Pittsburgh CLO.

By that time, Freeland was several months into his new day job at Alumni. The company had been seeking a new AD since founder Hallie Donner retired in 2024. The idea of a company dedicated to training young Black performers and producing shows featuring them echoed Freeland’s formative experiences at Arena Players.

“I was really thinking about my purpose in life and what I hope to leave behind as a legacy, and what I felt like could be fulfilling,” he says. “ATC always aligned, because it was like having that version of what I grew up with.”

The Larimer-based nonprofit works with 45 students grades 6 to 12 from around the region. About 80 other members have studied at Alumni over the years, including professional-level members who still perform in shows and take classes.

This season, Freeland’s second with the company, is Alumni’s 18th. Its theme is coming-of-age stories. One was “Akeelah and the Bee,” the stage adaptation of the popular film. Closing the season is Lynn Ahrens and Stephen Flaherty’s “Once on This Island,” the 1990 Broadway hit based on Rosa Guy’s novel “My Love, My Love; or, The Peasant Girl,” itself a retelling of the fairy tale “The Little Mermaid” set in the Caribbean.

“I did this play when I was 12 years old and it never left me,” says Freeland.

“The Human Heart” is one of his all-time favorite songs. And the character who sings it for Alumni will be played by another blast from Freeland’s past.

Kim Exum is known as the longest-tenured Nabulungi in the 2011 Broadway smash “The Book of Mormon.” She’s also a Baltimore native who was a youthful colleague of Freeland’s at Arena Players, where she once played Dorothy to his Wiz in “The Wiz.”

“We haven’t shared creative space in over 20 years,” Freeland says.

He recruits seasoned pros like the New York City-based Exum in part as inspiration for Alumni members.

“She has just been an amazing force of example of what it means to put in the work,” he says.

The kids have been watching the Broadway star in rehearsal.

“Some of them melt when she starts to sing,” Freeland says. “It’s been a joyous reunion to have her a part of this production because she understands the essence of ATC and what it means.”

The cast of 27 includes teens, pre-teens and a few professional Alumni members.

A number of ATC students over the years have gone on to wider acclaim.

DaMya Gruley starred on “Black Lady Sketch Comedy” and is now a comedy star on social media. In August, DeVaughn Robinson, now based in Las Vegas, will star in Pittsburgh Playwrights’ production of “BURNBABYBURN! the american dream,” the new play by ATC alum a.k. payne. And Kat Bruce, the recent Point Park graduate who’ll play the lead role of Ti Moune in “Once On This Island” will also star in “BURNBABYBURN!”

Freeland says the message to current students is, “This can be you. This is not a myth. This is not something that’s so far away and out of touch that you can’t reach. You can. These people did it, you can do it.”