Let me paint you a picture of cultural alchemy. Imagine the ghosts of British colonial officers watching from their subterranean WWII bunker as 6,300 Singaporeans sway to homegrown R&B beneath the banyan trees. Picture the prime minister casually auctioning his autographed guitar for $650,000 between sets by underground punk bands. Envision three generations of singers riffing together like this wasn’t some marketing gimmick but actually good fun. That’s Sing60 in a nutshell. The musical equivalent of throwing every ingredient in your fridge into a wok and somehow creating kaya toast ice cream.

Now, I’ve been to enough music festivals to smell a government initiative pretending to be Coachella. But something different happened in that muggy December air. When Benjamin Kheng brought out his old Sam Willows bandmates for a surprise reunion, the roar from the crowd wasn’t polite applause. It was the sound of twenty somethings time traveling back to 2014 playlists, forty somethings remembering their first romances set to local pop, and actual teenagers screaming because TikTok made vintage Singaporean indie cool again. I saw a grandma in an Iman Fandi jersey. This is not normal.

What slapped me across the face wasn’t the talent, though Singapore’s musicians could weaponize their hooks if they wanted. It was the pay it forward model selling adult tickets at $60 to fund underserved youth attendees. Festivals love slapping “community driven” on VIP bottle service events, but watching 60 kid guitarists perform before handing PM Wong’s donated six string cheque to Sea Limited’s billionaire founder? That’s theatre you can’t fake. Though part of me wonders if the teens whispered “Keep thr politics out of my R&B” backstage.

Here’s where critics might smirk. Oh look, Singapore commodifying heritage again, turning nostalgia into neatly packaged charity galas. To which I say. Have you met the internet We’re all doing this. Taylor Swift revives her old eras for stadium catharsis. K drama remakes of 90s classics dominate streaming. Everyone’s mining the past because the present feels unstable. What makes Sing60 fascinating isn’t the retro factor, it’s how aggressively they’re betting on new voices. Post hardcore bands sharing stages with 1970s Talentime winners. Experimental electronic DJs rattling wartime bunkers while indie pop floats across the lawns. This isn’t your national day variety show. It’s a generational mixer where nobody knows which decade to dance to.

Let’s talk about that $650,000 guitar, though. Part genius charity move, part power flex. PM Wong donating his axe for auction feels ripped from a celebrity telethon, until you learn the winning bid came from tech giant Sea Limited. The symbolism writes itself. Government and Big Tech playing nice through arts funding. But dig deeper and you hit radical soil. Gift A Guitar isn’t just giving instruments. It’s handing microphones. When 16 year old Himani and La Marcus presented that guitar onstage, they weren’t just beneficiaries. They were curators deciding who got to amplify their scene next. That’s lighting a fire under Singapore’s sometimes too polite creative class.

Watching Charlie Lim and Corrinne May perform together took me back to 2008 Singapore Idol auditions, all nervous energy and bottled dreams. The difference now? No reality TV cameras judging their worth. Just two artists who survived the showbiz grinder collaborating because they wanted to. Over at the Battlebox bunker, producers like Debbie Chia weren’t reminiscing about glory days. They were inventing new ones with beats that made ancient concrete walls sweat. Meanwhile at the food village, hawkers slung chilli crab tacos and elder aunties debated chess moves like this cross cultural collage was completely ordinary. Singapore is ready to stop apologizing for its chaotic creative identity.

I’ll admit something. As an entertainment journalist, I’ve rolled my eyes at “support local talent” campaigns that feel like homework assignments. Sing60 made me recklessly optimistic. Maybe because when Lady Kash spat bars about identity politics to a crowd spanning teens to pensioners, nobody looked confused. When The Great Spy Experiment’s post punk riffs collided with Mavis Hee’s Mandopop ballads, it didn’t sound like a compromise. It sounded like a city finally comfortable with its own weird contradictions.

The festival’s true legacy won’t be the funds raised or politicians photobombing. It’s proving that Singaporean audiences are starved for storytelling that doesn’t treat local culture like a museum exhibit. Nobody needs another sentimental ode to kampung spirit. They want messy, alive creations. Like that viral lunch break when 60 guitar kids tore through a pop punk medley before rush hour. Or why karaoke legends from the 80s happily shared billing with TikTok born rappers. My hot take The government backed arts event accidentally became cool because it stopped trying to be important and just let artists raid the generational pantry.

As the sun set over Fort Canning, I watched a group of teens teach some elders the TikTok dance to Shye’s latest single. The elders retaliated with old school Talentime jams. Someone launched into Stefanie Sun. A glorious cultural pileup ensued. That’s the magic trick Sing60 pulled off. For two days, Fort Canning Park became less a venue than a mixtape passed between friends. The songlist mattering less than the act of sharing it. And unlike those nostalgic concerts spoon feeding us heritage, this one left the next track up for grabs.