In the last two years, Wilton High School’s Freeplay: A Night of Improv Comedy show has grown immensely from its humble beginnings as a small improv comedy club started by a group of freshmen and its director Heather DeLude. This year there will be three shows at the high school’s Little Theater:


  • Thursday, Jan. 28 at 7:30 p.m.

  • Friday, Jan. 29 at 8 p.m.

  • Saturday, Jan. 30 at 8 p.m.


DeLude, an English and theater arts teacher at the high school, is an alumna of the Second City Conservatory in Chicago, where she worked in the late 90s.

“It was a really exciting time. I was really lucky,” DeLude told The Bulletin in 2014. “The class that I was in just happened to be a class that produced a lot of people that work in comedy today.”

Comedian Jason Sudeikis was in DeLude’s entering class at the conservatory, and Tina Fey and Rachel Dratch were on main stage.

“Being there in the late 90s was a really great time to be there,” said DeLude. “I didn’t realize how many people I was meeting and how they would end up shaping comedy.”

In 2013, DeLude started an improvisation club at the high school with a group of about 10 students who knew about and expressed interest in her professional improvisation background. At first, DeLude said, “a lot of people didn’t really flock to it.”

During the club’s weekly rehearsals, DeLude taught the students sophisticated improvisational skills she had learned at the Second City Conservatory.

The following year, the club put on the high school’s first Freeplay: A Night of Improv Comedy, where each show is guided by audience participation and no two nights are the same.

More than 70 students auditioned to be part of two casts for this year’s production.

The Freeplay production boasts a cast of 50 improvisers, a backstage crew, a professional piano player and student-run band and television production crew.

A group of Wilton High School students in an organization called WE-TV will broadcast this year’s production, and all the shows will be streamed over the Internet and Channel 78.

Tickets, to be sold during the lunch waves at the high school and at the door, are $10 for students and $12 for adults. Seating is general admission.