WESTPORT — Greens Farms Academy junior and Westport resident David Hoffman has been performing since he was little.

He has performed with the Musical Theater of Connecticut, Center Stage Theater Company, Applause New York and at the New York Musical Theatre Festival.

In countless shows he has sang and acted, one of which was “Guys and Dolls.” In it, the then seventh-grader starred as the high-rolling Sky Masterson.

“It was awesome, I loved it,” Hoffman said.

Next week, Hoffman will again star in “Guys and Dolls,” though this time as Sky’s gambling mate, Nathan Detroit, in Greens Farms Academy’ spring musical running Nov. 16-18.

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For tickets and times, visit www.gfacademy.org/theatre.

“Going around the second time, I didn’t want to play the same role. I realized as I was playing Sky that it’s amazing character, but that Nathan Detroit gets the laughs and has the more fun role,” Hoffman said.

According to fellow Westport resident Stephen Stout, Greens Farms’ director of theater programs and the director of the spring musical, Hoffman was well-suited to the role of Nathan Detroit precisely because it’s not a typical role for him.

“It’s primarily an acting role and that’s wonderful. I know he’s always going to be singing, but he’s pushing himself. It serves him well not singing all the notes in the piece and instead playing the wisecracking Nathan instead,” Stout said. “He’s eating it up and doing very well.”

“Sky is definitely the singing lead, while Nathan has more of the acting weight in the show. I am used to more songs in a show. And Nathan’s a very complex character in that he interacts with lots of different people throughout the show,” said Hoffman.

Hoffman will be joined by junior Patrick Howard, of Darien, who will play Sky, senior Macy Lawton, of Trumbull, who will play Sky’s love interest Sarah Brown, and senior Darcy Whitman, of Stamford, who will play Nathan’s romantic partner, Miss Adelaide.

Auditions began for the play in August, from which point the hopefuls were whittled down to a cast of 29 performers and six stage managers from Greens Farms’ Upper School. Rehearsals began after Labor Day with the cast and crew meeting two hours a day for eight weeks.

“It goes faster than you’d think, with days off and holidays and such. It can feel like a lot of time in some cases, and in others it’s like, ‘Whoa! How did that happen?’” Stout said. In this case, he said his crew is right where they need to be for opening night.

In addition to the cast and crew, Head of School Janet Hartwell, who will retire at the end of the academic year, and Associate Head of School Chris Kolovos will make cameos, as will two Lower School students selected in a raffle. The latter was devised, in part, Stout said, to get more people across schools involved and get more “fannies in the seats.”

The choice to perform the Tony Award-winning musical was made, in part, because of the actors at Stout’s disposal. According to the director, a solid group — 10 to 14 — of “gambler-type” guys is needed to pull the show off. Last year, the theater department graduated many of its female actors and a solid group of leading men emerged.

“I try really hard to serve the students, and I think we have. It is a little like riding a wild horse and shooting at a moving target,” Stout said, of the selection process.

Stout, an actor in his own right, with nearly 30 years experience appearing in TV commercials, on Broadway and in off-Broadway plays, came to Greens Farms about 15 years ago.

“I started teaching because I was a parent here. When they first asked, I said, ‘That’s cute. I’m not a teacher, but thank you.’ Then I decided I’d do it,” Stout remembered. “I had a career, and now I have another career, and they’re very much related.”

Having a director with experience under his belt is something his students appreciate.

“Besides all his acting credits, he also is a really good person and he knows how to interact with kids,” Hoffman said. “There aren’t many directors like Mr. Stout that know how to work with younger actors and pull a scene from them.”

justin.papp@scni.com; @justinjpapp1