It’s not unusual for an actor to play two roles in a play, especially in community theater, but when one character is an actor playing another character in a play within a play, things can get confusing.

That’s the acting challenge facing Wilton’s Stephen DiRocco and his castmates in Play On!, a comedy presented by the Town Players of New Canaan beginning Friday, Oct. 27, at the Powerhouse Performing Arts Center in Waveny Park.

Written by Rick Abbot, the show revolves around a cast of community theater actors who are just four days from opening night when a dim-witted but egotistical playwright keeps revising the script for a murder mystery they must perform.

The cast members switch back and forth between performing in Play On! and the play within called Murder Most Foul. DiRocco plays an actor named Henry Benish who plays a character named Lord Dudley.

“When you do two [distinct] characters in a play, they are two separate people and you can separate them in your performance,” DiRocco said, but in this case he is playing an actor and also “playing the actor playing the character. You have to put the character you’re portraying into the character he is portraying. In the middle of rehearsal of the play within a play, you break that character to that of the actor. You are changing accents, etc., playing two characters so they don’t overlap,” he said.

To keep things straight in his own head, DiRocco highlighted his lines in two different colors in his script.

“Here is the English accent, here I’m the actor. It is a daunting project. If something goes wrong on stage as an actor, I am breaking character and becoming Henry.”

Although he has more lines as Lord Dudley, DiRocco said Henry is probably the more challenging character in that he is a more clearly developed person.

“I’ve never done a play within a play before,” DiRocco said. Some years ago he portrayed two characters in Then There Were None at the Wilton Playshop, but they were not related in any way. “It was much easier to separate out.”

DiRocco finds his current role fascinating. “It was challenging at first — we were all getting into the swing of it.”

Henry is a mild-mannered husband and Lord Dudley is sterner. “They are different from each other. What’s challenging is behaving one way and then behaving another way,” DiRocco said.

Over the past 13 years, DiRocco estimates, he has performed in 50 to 60 community theater productions from Danbury to Milford. His most recent outing with the Wilton Playshop was She Loves Me.

“I’m a character actor. I like playing quirky characters. I’m definitely not a leading man,” he said with a laugh. For his day job he works in business administration and property management. He’s lived in Wilton for 17 years.

Play On! is “amazingly funny slapstick, the Noises Off of community theater,” he said, and while he’s never been in the same circumstances of the play, there are many things he can relate to.

Show dates are Friday and Saturday, Oct. 27 and 28 and Nov. 3, 4, 10, and 11, at 8 p.m., and Sunday, Oct. 29 and Nov. 5, at 2:30. Tickets and other information: 203-594-3636 or tpnc.org.