Successful business: High school seniors reflect on four years of theater

People have their own opinions of what success looks like and how to obtain it.

That’s what makes this weekend’s production of How to Succeed In Business Without Really Trying at Trumbull High School so compelling, as the award-winning cast tries to hone in on the message of Frank Loesser’s mischievous farce.

“My favorite part is that every character is trying to succeed in business without really trying, whether it’s Biggley or Womper or the protagonist, Finch — even all the secretaries are trying to maneuver their way up the company ladder, and they all have their own way of doing it,” said senior Alex Luft who plays Hedy LaRue, the secret mistress of World Wide Wicket Company president J.B. Biggley.

“They’re all trying to schmooze one another,” added senior Michael Lepore, who plays the main character, J. Pierrepont Finch.  

“Finch is the lead guy because he’s having the most fun doing it and that’s what makes him interesting,” Michael said about a character who, with the use of a self-help book, goes from window washer to top executive at World Wide Wickets.

The show will run Thursday, March 17, through Sunday, March 20, in the high school’s auditorium — a place where seniors like Michael, a two-time Connecticut High School Music Theater Award Winner for Outstanding Actor in a Supporting Role, feel at home.

“There’s something about spending so much time in here and doing it over and over again that makes you feel very comfortable and very excited to perform,” he said, discussing  how he felt about feeling nervous on stage.

“I don’t feel like there’s any pressure when we go out there, but it’s sad for us seniors that this is our last hurrah,” he said. “This is what we do — we’re always here, and it’s weird for it come to an end.”

Fellow senior Ava Gallo, who plays Finch’s love interest, Rosemary Pilkington, agreed that it is a unique bond that is shared among those in the high school’s theater program.

Reflecting on their four years of success at Trumbull High, the senior group recalled putting on a wide variety of shows, from Rent their sophomore year to Hello, Dolly last year as juniors.

“We’ve hit quite a range since we were freshmen, from the American Midwest in the 19th Century to New York City in the 1980s to jumping back to turn-of-the-century America last year,” said senior Jack Leonard, who plays personnel manager Mr. Bratt. “Now we’re here at the end of the 1950s between all those periods and on the outset of a very important decade in American history.”

While all the seniors agreed that their favorite production was Rent, they all look ahead with excitement to this week’s show, which includes 44 casts members who have been rehearsing 10-plus hours a week since Jan. 4 under the leadership of English teacher Jessica Spillane, a six-time nominee for Outstanding Direction from the CHSMTA, and 2015 winner of the Educational Theatre Association’s Inspirational Educator Award.  

“It’s a lot of fun because you’re doing something with your friends,” Ava explained. “When talking to other kids who do other activities like sports or other extracurriculars, they can’t believe we’d want to be here all weekend, but we really do, and that’s because we all love each other and we love being part of this incredible process.”

Getting into character

While the young thespians are plenty used to wearing makeup and costumes, How to Succeed in Business Without Really Trying presents them with a unique challenge they haven’t had to face before.

“I’m 16 right now and I’m playing a 75-year-old man,” said junior Liam Pierce, who plays Wally Womper, the chairman of the World Wide Wicket Company.

“I’ve been getting into my character by looking at my grandparents and trying to do what they’re doing — how they’re moving,” he said.

Liam, like many of his castmates, said he has gotten a lot of character help from Ms. Spillane, who has her student actors read the script repeatedly during their extensive rehearsals.

“We get to ask a lot of questions while we go through it, and that really helps us with the character,” Liam explained. “She wants us to do that, and I’ve found it critical to understanding who I’m playing.”

“Being an English teacher, she really cares about character development, and you get a great sense of that in pre-production,” Michael added.

The acting process wasn’t easy for all members of the cast, as the gender roles of the 1950s and 1960s irked some as they tried to get to know their characters.

“My character just wants to get married and play the role of housewife, and that’s not something I totally believe in,” said Ava. “I got frustrated with her a lot during our early rehearsals, but I realized that’s part of the time period.”

Despite appearing stereotypical on the surface, Ava came to understand that Rosemary has a lot of depth as a character in the play.

“She’s trying to marry Finch but she has a plan for herself, and that’s progressive in its own way for that time period,” the senior said.

Michael feels that this year in particular everybody’s playing a character that’s a “far step” from their real personalities — one final acting challenge before the curtain drops for good on the Class of 2016 after its last performance, scheduled for 2:00 p.m. Sunday.

“This show embellishes a lot about business and I don’t think any of us are taking it as something that’s overly serious,” he said.

“We’re going to the extreme versions of ourselves,” Ava added.

Listen to the music

Mimi Leonard, the assistant music director of the show, said she is looking forward to what the “wickedly talented” cast can do with some of the big company numbers — Brotherhood of Man, I Believe in You, and Coffee Break.

“There are a lot of harmonies people wouldn’t know unless they were looking for it, and it’s impressive how this cast is handling all their harmonies,” said the THS junior, who works under musical director Jerold Goldstein.

Musically, this year’s play differs in a lot of ways from last year’s spring musical, Hello, Dolly.

“We have the same amount of music but the style is much more contemporary,” Mimi said. “Last year we were at the turn of the century; this time around, we’re in the 1950s on the cusp of something much bigger and louder.”

She added that her favorite part of the musical numbers this year was the way Loesser included specific phrases and words that wouldn’t work in any other setting.

“There’s one line — irresponsible dress manufacturer — that when put into a song you don’t think it could work but it comes out sounding pretty amazing,” Mimi said. “All the wording is very unique — there’s nothing else like it any other play.”

While the audience members might be unfamiliar with some of the tunes, the junior song coordinator said that might be a benefit to those singing on stage.

“It’s a big show that’s been performed by a lot of famous actors over the years, but not many people know the songs,” she said. “They’re not like anything that comes out of Les Misérables or Jersey Boys; they’re not songs you’d throw on randomly to sing along to — they fit in this specific setting with this specific story.”

Going out with a bang

For their final week of rehearsals — known among cast and crew members as “tech week,” the group dedicates 11 hours a day before performing the first show.

“We basically go to school and don’t see the sun,” Jack joked.

The final product will be well worth it for the audience, but for the cast it’s all about the ride.

“This is one of the most talented casts we’ve ever had,” Alex said. “I’m so happy we’ve all been here and part of each other’s lives for the past four years.

And that’s the greatest harmony of all — a group of kids who have bonded so much over their high school careers that they’ve become a family.

“There’s a sense of it being the last one makes it sad, but we’re trying to make the most of it,” Michael said.

“I feel really confident in this show,” Jack added. “We’re going to go out with a bang.”

Tickets may be purchased online at or at the door. All shows except for Sunday’s matinee will start at 7:30 p.m.