Step into the world of Regina Song

For any millennial pressing play on Regina Song for the first time (like this writer), her music will bring you back to your girlhood – when love was all-consuming and every micro heartbreak deserved its own anthem. Her lyrics, often about unrequited love or admitting to a crush, drift over gentle melodies, carried by light, mellow vocals. Her songs feel like an intimate glimpse into her late-night diary entries, a sound reminiscent of early Taylor Swift or IU.

The diaristic songwriter lets on that her best work happens just before bed, when she’s “super duper tired”.

“I always get into the best flow when I’m sleepy,” she shares with a sheepish smile. It’s fitting, given that her online moniker is @sleepyreggy, and the name she’s given her fans: Sleepyheads. How adorable – and entirely on brand.

Going viral

In true Gen Z fashion, Regina’s rise to fame began with a Tiktok video. Lasting just 43 seconds, it featured a snippet of her singing The Cutest Pair on stage at The Peranakan Museum last August, as part of the programme for Singapore Night Festival. Dressed in a red top, black tiered miniskirt and slouchy white socks, Regina poured her heart into the lyrics: “No one can love you like I do / so baby think it through / for years and years I pined for only you, my baby.”

The clip, raw and unpolished, was a spontaneous decision. She had noticed other artistes posting live performance clips on Tiktok, and figured she’d give it a shot. The next morning, she woke up to 150K views. By the end of the day, it had racked up over a million views.

“The video wasn’t perfect, the audio wasn’t the best. I didn’t look super polished,” Regina reflects. “But for some reason, people just like the video. And honestly, I’m still shocked.”

That viral moment in September snowballed when fans began using the audio for their own Tiktoks, spreading her music further than she’d ever imagined. While she knew The Cutest Pair had potential, she never expected it to strike a chord with so many.

“It was the first time I saw so many people engaging with my music. Virality aside, I’m just happy there are people who enjoy it – and that I’m not like, delusional,” she says with a self-deprecating chuckle.

That same month, the track soared to No. 3 on Spotify’s Global Viral Chart. By November, Regina announced her first South-east Asia tour, Fangirl: The Tour, which took her to Kuala Lumpur, Bangkok, Jakarta and Manila throughout January.

“It has been very unexpected,” she admits. “Everything just happened so fast.”

Music in the age of algorithms

While The Cutest Pair remains her biggest hit to date – with over 38 millions streams on Spotify, 25.5 million views on Tiktok and nearly 950K plays on Youtube –Regina doesn’t feel the pressure to replicate its viral success.

“I’ve always been someone who writes songs very diaristically. I feel like there is no point in writing a song for the charts,” she says.

Her latest single, Fairy, is a prime example. A marked departure from the dreamy, girlie pop of her debut album Fangirl, this track channels the raw emotion of a break-up – the resulting hurt, anger and disappointment, with lyrics like: “I want out of your life / but you act so unwise / if you think that I would come back to you running, darling, think twice.”

The rising pop star reveals that the single was written after the dissolution of her first real relationship “a few months back”. It had lasted one and a half years.

“Even if [a song] doesn’t gain 38 million streams, I’m totally OK with it,” she shares coolly. “The point of being an artiste isn’t to be commercially successful – it’s about being authentic with myself. If [my songs] gain traction, that’s an added bonus.”

Still, Regina admits to keeping an eye on her numbers to gauge her content’s engagement. “Sometimes, I do feel like it’s a never-ending race,” she says. “Like, I can’t lose relevance. I can’t stop my steam.”

But then comes a surprising moment of reflection – one that reveals a quiet confidence rare for a singer her age: “I also remind myself that I’m primarily an artiste, not a content creator… it’s OK if my videos don’t do well right now.”

Growing into her sound

The songstress’ journey into music began with a piano at the tender age of six.

“According to my mum, I asked for piano lessons. But I don’t remember really liking it, I remember crying on the way to the lessons sometimes,” she recalls. Still, quitting wasn’t in her nature, so she stuck with it.

By the time she reached Grade Five in Primary Six, her mother suggested auditioning for the School of the Arts Singapore (SOTA) to nurture her interest in music. She got in, majoring in classical piano – but soon realised that it gave her performance anxiety. Regina considered switching to voice, but her teachers advised against it, citing that she had already devoted four years to her craft then. Instead, they offered her vocal studies as a minor.

“That changed a lot of things for me,” she reflects. “I’m really glad they gave me that opportunity to train my vocals. If not, I wouldn’t be where I am now.”

Regina recalls writing songs since young – first as a kid in her bedroom with her cousins, then later as a teen, especially with her long-time best friend, schoolmate and fellow artiste Rhyu. Upon her graduation from SOTA in 2022, the then 18-year-old realised that she had built up an entire vault of songs. That’s when she made a bold decision: to take a gap year to focus on songwriting. Her parents had just one condition – she had to support herself financially.

For the next three months, she juggled studio sessions with shifts as a barista, making just $8 an hour.

“I really felt the struggle,” the breakout star confesses. But looking back, she wouldn’t change a thing.

“I gained a lot through that experience, I learnt a lot about myself, like how tenacious I could be,” she shares. “And it really motivated me to make my music career work.”

Fortunately, the musician has had unwavering support from her parents, who, as it turns out, are uniquely equipped to help her navigate her budding career. Her mother, who used to be an executive assistant, helped with booking flights and selecting accommodations for Regina’s first tour. Her father, a digital marketer, oversees her Spotify and social media ads to help promote her music.

“My dad is very much into numbers. He made a whole table of my Spotify streams to help me calculate my potential income,” she divulges, her tone equal parts amused and incredulous.

“I’m really fortunate to have parents who are so willing to help,” she adds.

Into the Sleepreggy-verse

This year is shaping up to be a busy year for the viral sensation. At the end of this month, she’s set to release Love Me Again, another soul-baring single born from the same emotional terrain as Fairy.

Written in the wake of her break-up – one that she initiated – Love Me Again lingers in the emotional aftermath, with the lyrics going: “But if said I still love you / would you take it / would you love me again right now.”

“It’s the first truly sad song that I’ve written,” she admits.

There’s more. She’s dropping her second album in the later half of this year, a project that she describes as an invitation into a world of her own making.

“I daydream a lot for my art,” she says wistfully. To her, daydreaming isn’t just a pastime - it’s a kind of manifestation.

“Daydreamers are always inspired,” she muses. “And to live an inspired life? That’s a good life.”

PHOTOGRAPHY SHAWN PAUL TAN 
CREATIVE DIRECTION & STYLING LENA KAMARUDIN, ASSISTED BY LATISHA SONIA SHAYMENTYRAN & JEON JAE WON
ART DIRECTION RAY TICSAY
HAIR ZHOU AIYI
MAKEUP LASALLE LEE, USING DIOR BEAUTY
MANICURE FLUTTERY TIPS
LOCATION SERANGOON HOUSE