Ivan Heng: 'I am a serial cross dresser'

What's Emily Gan hiding underneath all that makeup and hair spray?

Apparently enough for theater veteran Ivan Heng to choose Madge's signature "Material Girl" tune as a lynchpin to update one of Singapore’s most iconic screenplays, "Emily of Emerald Hill."

Like the video where a diamond-and-gown clad Madonna sings about living in a material world, the play revolves around lead character Emily Gan's costly climb up society's ladder. 

The song inserts a pop cultural feel to the play set in 1940s and 1950s Singapore and is also the anchor point of the promo teasers featuring Heng dressed as Emily currently circulating on Facebook.

More on CNNGo: Emily of Emerald Hill Ivan Heng: 'We wanted to reach out to a new generation of theater goers'

Ever the tease, Heng shares more on what to expect from this decade's version of "Emily of Emerald Hill."

CNNGo: It’s been a decade since you’ve played Emily Gan, how does it feel to come full circle?

Ivan Heng: Stella Kon the playwright wrote me a sweet note to say, “Ah you are approaching the role again, it’s like donning an old kebaya, you have to work at it to get into it, but once on, it feels comfortable and familiar.”

I think that it’s not quite comfortable yet, there’s some work to go, but we will get there. It’s a classic; we can’t just revive it or hit the refresh button. It’s about making it new again.

CNNGo: Times have changed, how are you playing Emily differently from 10 years ago?

Heng: I am stronger and weaker. I am more innocent and more jaded. I am harder and I am softer. Age has allowed me to be more empathetic. So I think that being 10 years older gives me a range that’s wider.

It’s great that I have Glen Goei as my director, we have done a lot of crazy things together and I can feel him willing me on. It’s a deep and intimate collaboration.

Our Emily has become softer. She looks at life in a more philosophical way, understanding that it’s full of ups and downs, good and bad. That’s when the play becomes profound.

CNNGo: So is Emily a true material girl?

Heng: She is the first Singaporean citizen of the world.

This is a woman who is Chinese, wears Malay clothes, eats pork, sends her son to England to study, buys American barbecue grills, wears ball gowns from Europe, studies Malay, French and English with a personal tutor, she is global.

I have had women and men from different cultures come up to me and say, “You are my grandmother, you are my mother, I know this woman.”

They are Japanese, Jewish, Indian, Australian. Kon has written something that is interesting, beautiful and universal. It’s no wonder this play has traveled.

CNNGo: You’re the only man to ever play Emily in its 28-year history, but it also seems to be a W!ld Rice thing to cross dress ...

Heng: We like to question the idea of roles and gender and the audience takes great pleasure in it.

The idea of a role like Emily is interesting because I am a serial cross dresser. It’s not done in a cheap way. It’s done with intelligence, sophistication and polish.

It’s hard work though, you have to be plucked, trimmed, powdered, waxed and corseted. And the corset is much harder 10 years later.

CNNGo: How exactly do you play her then?

Heng: Theater is about dramatic irony. When I play her I don’t play her campy, I play her under the skin as a woman.

We are all playing a role that society has assigned. Women must be beautiful, women must fix their hair, and women must be well behaved.

In W!ld Rice, we like to spin that notion of gender around and underneath it is a political point of view.