Benjamin Kheng had no idea how difficult marriage would be. Some might find it shocking, especially those who only know Kheng through the socially distanced celebrity lens.
Here is this boy who grew into a man in the harsh glare of the spotlight, when he first burst onto the scene over a decade ago with the popular quartet The Sam Willows, his sharp, angular face, floppy hair, and impeccable fashion sense blending to create the prototype pop star. Even after the band’s hiatus in 2019, he made music that clocked tens of millions of streams, and garnered followers with his quirky comedic content.
The perfect culmination: a beautiful romance that blossomed into a wedding with artist Naomi Yeo. Korean drama script writers couldn’t have come up with a better story arc.
But life still continues after the credits roll. “Everyone thinks they are good listeners. Then they get married,” muses Kheng, now the elder statesman of pop and social media at 34. “There are so many things that you think you are. Marriage, however, has a way of both humbling you and making you better.”
The marriage isn’t in dire straits. Rather, it’s the journey every newlywed couple goes through. When you marry someone, you don’t just marry their personality. You also marry their baggage, and Kheng realised he had some childhood hang-ups deep inside his psyche that he needed to let go of.

Photo: Joel Low
In the aftermath of losing his mother when he was a child, he developed separation anxiety, which he still has today.
He knew he feared being apart from loved ones for too long. Until recently, he didn’t realise how much it still affected him. It was a sobering realisation, but Kheng has great self-awareness and with it, a willingness to change. For him, like the video games he loves to play, it was just another level to overcome. “I love it. It’s been great.”
Kheng’s career, too, is approaching exit velocity. His 10 years of building his repertoire and reputation have enabled him to take time off to evaluate his next steps. He loves his work. Now, he wants to make it last.
He’s seen so many in the industry blaze in like a shooting star, and then flame out just as quickly. Kheng doesn’t blame them. He was once an impressionable man who wanted to change the world as well.
“I loved everybody and spread good vibes and I believed in hard work and being a good person. But there are parts of the industry that have a way of crushing your spirit,” says Kheng. “You see how people value things, or how they are rewarded differently. You get jaded.”
In addition, it made him unknowingly more competitive in an unhealthy way. He became more selfish and self-serving, initially rationalising his stance as a way to “protect my energy”. However, over time, he realised it actually drained his reserves.
“What gave me energy was to care genuinely about someone. That goes a long way in an inherently narcissistic industry,” says Kheng. This awareness didn’t come easily. It took several years of self-confrontation and brutal honesty. The latter was especially hard. No one enjoys facing their shortcomings, to realise that they are inherently flawed. But there is beauty in struggle and Kheng is now a vortex of positive vibes. He gives out smiles easily, like candy during Halloween, not worrying about how he’s perceived. “It’s incredibly infectious when you give out good energy in a public space,” he says.
Kheng might not be that young man with big hopes anymore, but the magnitude of his dreams remains the same. He wants to continue telling stories and finding innovative ways to do so. Ironically, taking his foot off the accelerator has allowed more interesting opportunities to enter his orbit.
He recently wrapped up filming for a boxing-centred drama production that will soon air locally. There are more projects coming up. He cannot give me more details, but he tells me he is excited and fearful at the same time. It’s the emotions you get when standing over the precipice, knowing you’re going to plunge headlong into something you’ve never done before. The rush will be unlike anything you’ve ever experienced. Kheng now has one foot over the edge.

Photo: Joel Low
I ask if we’re seeing his metamorphosis in real-time now, becoming version 3.0. “I’d say it’s version 2.0 Pro Max Plus,” he says, laughing. Age and time have whittled his ambition.
Even though he still wants to create great work, he won’t let success, or the lack of it, define his legacy. There is no longer an insatiable monster within him that he must feed with validation and awards.
“My sister, Narelle, has a great quote for this: ‘Healed people are naturally less ambitious because they are no longer trying to prove themselves’,” he shares.
Kheng has shown the world what he is capable of. Now, he just wants to show himself. Just another boss to defeat.
Read the other cover stories and see their cover shoots in the links below.

Photography Joel Low
Style and Art Direction Chia Wei Choong
Makeup Sha Shamsi, using Gucci Beauty
Hair Christvian Wu, using Kevin.Murphy
Photography Assistant Eddie Teo
Styling Assistants Julia Mae Wong & Caleb Lim





