Who exactly is Hossan Leong? A household name from his many appearances on television — whether in dramas or as a gameshow host, ‘Singapore Boy’ Hossan Leong’s story in the arts stretches far deeper. From his humble beginnings in theatre to receiving the prestigious French Chevalier de l’Ordre des Arts et des Lettres (The Order of Arts and Literature), his life is a testament to the evolution of Singapore’s cultural scene.

That journey takes centerstage in Hossan-ah! In The High Arts, a new show premiering at the 2025 edition of the Singapore International Festival of Arts (SIFA). In it, Hossan traces his personal trajectory through Singapore’s art scene, reflecting on four decades of development through his own lived experience — a parallel narrative to the nation’s own cultural awakening.

Interestingly, this will be Hossan’s first time performing at SIFA, despite his long tenure in the arts. “Natalie (Hennedige, Festival Director) approached me one day and said ‘eh, 2025 will be my last year as SIFA director,’ and wanted to know if there was any way I could be involved. I was like ‘SIFA? Me??’ People see me as a TV comedian, not someone in the ‘high arts.’ But that’s exactly why I said yes,” says Hossan. “We’re not changing the Hossan-ah brand; it’s still the same format, with me, a band, three girls, multimedia. But this time, it’s about more than me; it’s also about telling a parallel story of Singapore’s arts scene.”

“I guess it’s especially unexpected because people might think oh it’s so highfalutin, so I rolled with that idea and gave it the subtitle In The High Arts. I proposed that to Natalie and she rolled on the floor laughing. Before we knew it, we were scheduling photoshoots,” he adds. “It’s funny now that I think about it — I never saw myself as a comedian. My first play was The Necessary Stage’s Off Centre, and how comedic can that be? I just kept going, and somehow I eventually became known for comedy.”

This time, Hossan is also stepping back from his usual behind-the-scenes role, bringing in director Glen Goei to helm the production. “Glen’s a very visual person who understands the big picture, so it’s really allowed me to focus on the performance itself,” says Hossan. “And in creating Hossan-ah, Glen spent a lot of time just asking me questions that led me down memory lane. It really became a deep dive into my past.”

“You know, I’m one of those people who throws things out when I move house. I never thought I’d need to revisit these boxes of photographs, and digitising them is a pain,” he laughs. “But Glen has known me for years, and he asks all the right questions. It’s made me realise how many roles I’ve originated in Singapore theatre. I always felt like I was bumbling through my career, but revisiting everything has been fun — and cathartic. From the triumphs to the times I wondered when my next paycheck would come.”

Looking back, Hossan is struck by the growth of Singapore’s arts landscape: “Singapore’s English theatre scene only really emerged in the late 80s. So yes, we’ve had a short runway. Yet, I firmly believe we’ve produced some incredible local work that can rival the international stage.”

What stands out most to him, though, is the community. “We have so many colleagues working across companies and productions, and some become lifelong friends. I do wish we could coordinate our schedules better to avoid cannibalising each other’s audiences, but I’m always blown away by the talent.”

“Take Supervision by Wild Rice, which I watched recently; I was so impressed by Amirah Yahya, who came from Malay theatre. And seeing Julius Foo onstage — I realised it was the first time he was working with Glen. It’s great that we’re finally leaning into talent from all walks of life and backgrounds.”

Even now, Hossan remains hungry to learn. “I’m very lucky — I’ve never had to go hungry. But it’s scary when you start comparing yourself to others, wondering why you didn’t book that job. An artist’s self-esteem is fragile; plenty of comedians aren’t happy in real life!” he says. “I didn’t go to art school, so I sometimes feel like an imposter. But I make up for it by learning everything I can, whether from directors, actors, crew, so no one can say I didn’t try.”

“That’s just how I cope — by being better each day. I’m still looking for growth, whether it’s learning a new language or embracing tech in the arts. A lot of people my age have given up, but I believe you’re only as good as your last gig. The arts must fulfil you innately — money or stardom won’t sustain you.”

It’s that drive that pushes Hossan to create opportunities for others. “I was lucky to be given chances, so I always try to pay that forward. These days, you can enter the arts without your parents losing their minds, unlike in my day,” he laughs. “Established artists have to step outside our comfort zones, cast more widely, and take chances on others. We’re sowing seeds for the future.”

Hossan is passionate about how the arts builds life skills, not just careers. “When I teach acting, I’m teaching life skills like body awareness, emotional expression, not how to be a star. These are useful even in corporate settings, where you might have knowledge but can’t express yourself.”

That’s why Hossan-ah! In The High Arts isn’t just about laughter. It’s about accessibility and demystifying the “high arts”. “I hope people come curious — especially mainstream audiences who love comedy — and I can expose them to shows they might not usually consider. Kind of like how Broadway Beng brings the aunties and uncles to Western musicals, with a Hokkien twist,” says Hossan.

“If I can make them laugh, plant a seed, and get them to try something new, then I’ve succeeded. It’s frustrating when sponsors ask, ‘What’s the ROI?’ Maybe 20 years from now, someone who saw this will grow up to direct or support the arts. You can’t quantify that. But I hope people leave the theatre encouraged and uplifted.”

And what about audiences who are hesitant? “Nowadays, audiences want a sure thing — Taylor Swift, Kumar. But sometimes you need to take a leap of faith. I see my role as a guide to help them do that. Just buying a ticket supports the arts. Even if it doesn’t make sense now, maybe 20 years later, it will hit you. That’s the potential of the arts,” he says.

Finally, tying into SIFA’s 2025 theme of “More Than Ever”, Hossan reflects: “We’re surrounded by apathy. We talk about being a caring society, but we don’t practise it. It’s 2025 for goodness’ sake; why are we still dealing with racism and prejudice? The arts can spark dialogue. It helps us understand that different viewpoints can co-exist. It opens us up to empathy. And more than ever, that’s exactly what we need.”

Hossan-AH! In The High Arts plays from 30th May to 1st June 2025 at the Victoria Theatre. Tickets available from BookMyShow

The 2025 Singapore International Festival of Arts runs from 16th May to 1st June 2025. Tickets and more available here