SINGAPORE — As far as my music tastes go, I prefer what I call “emo Mando- or Cantopop” by artistes such as Jonathan Lim, Sammi Cheng, Sandy Lam and Anita Mui. So, when I was told I had to interview ShiGGa Shay — arguably Singapore’s hottest rapper right now — I turned to that delightful repository of musical encyclopaedic knowledge — YouTube.

I made several observations about rap stars: First, I noticed they nearly always wear their caps backwards, as if their necks, rather than their faces, needed protection from the sun. Second, they say “cool” and “man” a lot. Third, they always wear a scowl, as if half the world owed them money (which is a truism in some cases).

As I waited to meet ShiGGa Shay for the interview at Nassim Hill Bakery Bistro Bar, I readied myself for an intense figure and made a mental note not to borrow any money from him. But the 22-year-old turned out to be all grins, friendliness and easy manners — although he really did show up wearing his hat backwards.

“I wouldn’t say I am angry, but I was born with this kind of face,” the affable hip hop artist explained, when I asked why he always looked so cheesed off in his music videos. “If I don’t speak, people immediately get the impression that I am either angry or arrogant. But, you know, you can’t please everyone. Everyone is going to have his or her opinion of me. But the fact is, I am not angry — I just look like that. I was born looking like this!”

But he acknowledged rap artists can be intense, because of the nature of their work. “Most rappers are real, in the sense that they mean whatever they write in their lyrics. It’s not for fun and games,” he said. “Sometimes, it’s about getting their emotions out. Imagine if a rapper smiled all the time, it would feel very sugarcoated, and people would know it was fake.”

Yet, ShiGGa, whose real name is Pek Jin Shen, should have plenty to smile about. The rap artist has come a long way since his early days on the local music scene, making appearances at events and TV shows such as Live And Loaded, although it must be said that back then, he appeared a little rough around the edges. ShiGGa really came into his own after he took part in the music mentorship programme run by Noise Singapore, an initiative of the National Arts Council. Mentored by producer Don Richmond, he developed and sharpened his music style.

After releasing a series of videos and singles online, ShiGGa co-opted the Grizzle Grind Crew (GGC) — a 12-member collective featuring members such as Lineath, Charles Enero, Tosh Zhang and Wang Weiliang — which is celebrating its second anniversary this month. He even has a production company, Grizzle Films, and has established a respectable career in a branch of music no one would have thought viable just a few years ago.

“When I told people I wanted to do rap, they were like, ‘You’re crazy, man, there’s no way you’re going to make it’. And that was, like, three to four years ago, when local music wasn’t what it is now. Now you actually have a following and people come to the shows. But three years ago, nobody and nobody bought your stuff. It was a blind hustle. I just kept working and working, and trying to imagine that one day it would happen. But you didn’t know whether it was really going to happen,” he said.

Happen it has. Since releasing the hit singles Limpeh (2013) and Lion City Kia (2014), the Singapore Polytechnic alumnus has accumulated hundreds of thousands of views for his music videos on YouTube. The rapper also has several upcoming collaborations with prominent American hip hop artists and plans to expand his career to Malaysia and Taiwan. Come June, he will release his debut full-length album, which he said will contain a wide variety of tunes.

But music is just one of his passions. ShiGGa, who directs many of his own music videos, said he wants to direct his own movie, adding that his next single will be released in the form of a short film. (Incidentally, he will appear in his first acting role in Singaporean director Royston Tan’s latest movie, 3688, when it debuts later his year.) “Nowadays if a video is not on YouTube, it doesn’t exist at all. If your song doesn’t have a video, your song would disappear in like a few days. So I just want to find new ways to connect directly with the consumer,” he said about his videos.

Luckily for him, ShiGGa’s efforts have produced some fringe benefits. I told him I found it hard to believe that girls never paid attention to him before he became a rapper, as he claims in his latest single, ShiGGa Morning — which features cameos from popular YouTube stars such as Yan Kay Kay, Munah & Hirzi, singer Inch Chua and radio DJ Tabitha Nauser — especially because his WhatsApp profile reads, “Will reply if you’re hot”.

“It’s true!” exclaimed ShiGGa, who is currently single. “You know how in secondary school you have cliques? I was always with the losers, the ones who studied a lot. I didn’t really study a lot, but I was with them because I couldn’t click with anyone else. And I had eczema. People laughed at me and called me ‘the skin problem boy’. That messed up my self-esteem as a kid. I was so shy and I couldn’t talk to girls. During PE lessons, I was always the guy who got picked the last.”

“Then I performed at a Teachers’ Day show, and then suddenly I became the cool kid, and everyone was my friend.”

While ShiGGa probably does not expect his girlfriends to wear a cap backwards, he said the girl he wants to date has to know how to appreciate hip hop music. “If I had a girlfriend, she definitely has to listen to hip hop, because it’s like I’ve been in relationships where the other party doesn’t understand hip hop — and it’s not anything bad but it’ll be a problem for me because I talk about hip hop a lot,” he said. “And if the other party can’t understand my job, then it is very hard to communicate. If I had a girlfriend, she would definitely have to be a hip hop enthusiast.”

Only time will tell if he eventually meets the hip hop enthusiast of his dreams, but ShiGGa Shay and the rest of his crew are determined to share their love for hip hop with the rest of Singapore. The GGC will be holding a free concert — featuring acts such as Malaysia’s Joe Flizzow, America’s Dumbfoundead as well as Sleeq and Gentle Bones from Singapore — on Sunday to celebrate its second anniversary.

“There aren’t enough rappers doing it and being in the limelight consistently,” said ShiGGa. “I think this will change in the years to come.”

He added: “This is why we are doing all these concerts — to inspire the next generation, so there will be more rappers and more people creating content.”

Special thanks to Nassim Hill Bakery Bistro Bar. The CONFESSTIVAL X 2nd Grizzle Grind Crew Anniversary party will be held at *SCAPE The Ground Theatre on April 5. Admission is free. Visit scapers.sg/confesstival for more details.