Ellison Yuyang Tan also takes to the stage solo in Michelle Tan's I Am Trying To Say Something True, about a 28-year-old trying to cope with the loss of her job.
The 31-year-old playwright says the script began from her interest in words and the difficulty of finding the right thing to say in difficult situations.
"I thought about how words always fail in the face of loss or heartbreak, how what we don't say carries as much or even more weight than what we do say," says Michelle Tan, who co-wrote Cake Theatrical Productions' Ophelia for The Studios 2016.
"I wanted to explore that constant struggle of articulation - how and when do we begin to talk about loss? What is at stake when we do or do not speak of it? What does it take to be completely honest and why is it so difficult?"
Programmer Fezhah Maznan of The Esplanade Co says this season is about working with independent artists at various stages of their careers. "We also wanted to bring it back to just storytelling and the actor's body and explore that on stage."
Perhaps the most anticipated monologue this season is How Did The Cat Get So Fat?, first staged in 2006 by Teater Ekamatra and starring Siti.
Portraying multiple characters from the nine-year-old narrator to a taxi driver won her her first nomination for Best Actress at the annual Life Theatre Awards. Yeo Yann Yann took the palm that year for Thunderstorm by The Theatre Practice, but Siti, 32, says the play kick-started her career into higher gear. "It's one of the plays that's closest to my heart," she adds.
This time, she also has to manipulate puppets while acting, as director Tan Beng Tian and assistant director Daniel Sim add in The Finger Players' signature theatrical device.
The script has been updated to take out references to defunct technology, - including the iPod - but what has not changed is the story's heart: that pre-existing rules and norms work to constrain or disable sectors of Singaporean society.
The sketches are arranged along themes in the national pledge, such as religion, race and progress. Imbalance looms so large that the director says: "When I read the script, I was very sad."
Tan Beng Tian then engaged in deep discussions with playwright Zizi about whether or not she could add a note of hope to the story.
Not as much as the director would have liked, sadly. "At the end of the day, this play is talking about something that is amiss with our flag," she says. "Equality is an impossible idea, maybe. What we need is fairness."