San The Wordsmith
Writer, performer, rapper, musician—suffice to say, San The Wordsmith is an all-rounded creative through and through.
Having started his journey in the arts early on in his teens, San has since dabbled in most kinds of performance art, from theatre to acapella, and even to hip-hop and rap, which is what he’s best-known for today.
Now, barely in his mid-twenties, San already has a clear vision of where he would like go in his career—to be globally acclaimed. And if you ask us, we think he’s on the right track, having been shortlisted as one of 15 finalists in Vans Musicians Wanted Singapore in 2020, winning Fresh Off The Block in 2021/2022, becoming one of five budding bands at Baybeats 2023, and, come 20 January, being the third local artist (after Shye and Forests) to perform at Music Lane Okinawa.
Besides his penchant for hip-hop, smooth vocal tones, and sheer determination to work his way up in the industry, what we think sets San apart is his vulnerability. With lyrics inspired by his emotions and lived experiences, San’s music isn’t just catchy, but raw and relatable as well—something that he attributes to his late father, whose support and openness about his emotions remains the fuel to San’s fire for his craft today.
And perhaps this fire is why, even on an early weekday morning, San shows up bright-eyed, iced coffee in hand (his first of many), ready to tackle our shoot with Jeremy, his guitarist for the day.
Note: The video above includes a short snippet of the full interview, which is transcribed below.
Can you tell us more about your song, Counting My Days? What was the inspiration behind it?
San (S): People usually listen to my songs because I show a vulnerability that most don’t like showing, and Counting My Days is a song that I wrote when I was in the worst state ever—I had problems at home and problems with my then-girlfriend.
At the time, it felt like an amalgamation of the worst things possible that could have happened, and Counting My Days is just me telling people, “Yo, a lot of these things are happening, but please just stick around. I know part of the problem is me, but I’m constantly working on it, so please trust that it will get better.” That, in essence, is what Counting My Days is about.
On the topic of songwriting, we know you write poetry as well, so we wanted to ask, which came first for you—writing or rapping?
S: Writing, actually! I mean, as you just mentioned, I do poetry, and I used to do it constantly, so I’d say that I fell in love with poetry first. Rap is just a medium for me to bring words to life—it’s like a personification of my words, you know? I feel like I can express myself and my writing even better with rap.
How did writing evolve into rapping for you?
S: So roughly 10 years ago, I started out in my career as an artist at this place called 10 Square, which is an arts training centre for youth artists. Back then, it was where I did music (acoustic and acapella, not rap).
I did that while continuing to write poetry, and then halfway through, I think in 2016 or 2017, I realised that damn, I don’t wanna do acoustic music anymore. I wanna do hip-hop, I wanna do rap, because I had already been freestyling a lot since 2013. So I jumped ship and have been doing hip-hop ever since.
I still do acoustic stuff, R&B, and soul-ish music occasionally, but yeah, it just became rap and hip-hop all the way for me. But, I must say, please don’t look into my past guys. You didn’t hear this from me, please don’t look into this (laughs).
Moving on to San as a rapper now—you won Fresh Off The Block (FOTB) 21/22! Can you tell us more about what that experience was like for you?
S: Yeah! The organisers of FOTB and the guys behind YUNGTAUFOO are good friends of mine. It’s bad that I was categorising who I was as an artist, but I think at that point of time, I was still an underground artist, and FOTB brought me out of the mindset of thinking that I’m underground.
So all things considered, it was a nice event. I’m thankful that I got what I got, because it basically became the bridge to a lot more things. I met people from Left Mind, which is the collective that I’m with now, and a bunch of other guys in the local scene, so yeah, FOTB was just amazing honestly. It was a really big stepping stone for me—without it, I’d still be freestyling with random people on the streets.
On that note, what’s next for you?
S: Well, if you guys didn’t know—I mean, I’m sure you didn’t because I don’t tell this to everyone—I’m working towards getting a Grammy. If not getting a Grammy, then being nominated for a Grammy.
I’m constantly trying to work towards it, seeing what works, and I know I’m still far from it, but I believe that having a bigger goal allows you to really encapsulate and visualise your dream, which makes you realise what it is exactly that you need to do to achieve it. So it’s there, and I know it’s there, but I’m trying to think less about it and more about the steps that I’m taking to get there.
But if I’m talking about immediate stuff that’s lined up next, I have a number of things that I’m looking forward to, like small shows here and there, as well as a set with my band, The Workshop, at Music Lane Okinawa on 20 January. I’m thankful, very thankful, and it is very exciting, but also exhausting. But hey, I shouldn’t complain (laughs).
Back to music and writing now—who or what inspires you?
S: Ahh, okay, so this spectrum is huge for me, because if I talk about which group of artists inspired my music, I would say my number one inspiration is Boyz II Men. I love Boyz II Men—they inspired a lot of my lyricism. Other artists like J Cole and Saba inspired a lot of the musicality of my songs; guys like MFDoom, Nas, and Black Thought inspired my punchlines and the structure of most of my rap stuff; and vibes-wise, I would say Daniel Caesar, Sza, and John Mayer are huge inspirations.
How about in terms of your personal writing? Who inspires you in that aspect?
S: Boyz II Men—simple! With Boyz II Men, there’s this sense of personality in their songs that makes you think that they’re writing for you, you know? I used to write a lot of very vulnerable stuff, songs for partners or for family, and the direct reference I have is literally Boyz II Men, because they have songs that they’ve written about their moms, partners, and all.
So yeah, simple answer, Boyz II Men (laughs).
If you had to pick just one, what would you say your favourite Boyz II Men song is?
S: Ahh, just one? Can I do three?
3rd—End Of The Road
2nd—A Song For Mama
1st—It’s So Hard To Say Goodbye To Yesterday
These days, a lot of youths are getting into the local music scene, forming their own bands and attending gigs. How do you feel about this, and how else do you hope to see the local music scene evolve?
S: So here’s the thing, myself and some of the guys that I talk to—including other rappers like TENGY—are hoping that eventually in the next five to 10 years, in the local music scene, or more specifically, the local hip-hop music scene, people will be less afraid of creating and more excited to release their original music.
I think right now, people are just afraid of getting shunned, you know? People are afraid of what others might say, and maybe this applies to all genres of music in Singapore, but I mainly speak for the hip-hop community in Singapore. I feel like most of the newer guys, the newer cats, they’re just afraid of releasing their original stuff.
I hope that in five to 10 years, these younger aspiring artists will be inspired by my generation of artists, like TENGY, OmarKENOBI, Fariz Jabba, Yung Raja, and the list goes on. All of us used to post bedroom freestyles, and if the younger generation sees what we’ve done and where we are, knowing that we started from releasing bedroom freestyles, they’ll hopefully be less afraid to do the same.
A few people have come up to me and asked me, “What do you think about my music?”, and I’m always like “Dude, it’s cool! Just release it, don’t think twice about it”, and some of them are like “Oh, I have songs that I’ve made that I don’t release because I’m afraid of what people might say”, but I’m like “Stop that, put it out!”
One of the things that I’ve learned over the years is that you never really know how people will respond to your music until you put it out. So yeah, that’s about it lah. Hopefully in five to 10 years, we’ll be comfortable releasing music and people will be more receptive towards hip-hop, and maybe by then, having 200-300 people attending a local gig will be a regular thing.
Do you have any pre-show rituals or habits?
S: Let me think… not really, but actually, now that you’ve asked me, I realise that I always have coffee before a show. I think that’s the only pre-show ritual that I have.
Aside from that, all I really have is a habit, or rather belief when I’m performing—if I don’t leave the stage sweating, it means that I didn’t give my 100%.
What’s your go-to coffee order?
S: If there’s a coffeeshop nearby, then it’s kopi peng siew dai gao (iced coffee, less sugar, extra thick). Mmm, that extra kick. But if there aren’t any coffeeshop options, then I get a regular latte with three extra shots, so four shots total, from Coffee Bean or whatever is available. Is that weird?
That’s a lot of coffee.
S: Really ah? Damn, I thought it was normal, man. Usually I get four shots, but sometimes it’s just three. But always with milk. The only time I drink coffee without milk is if it’s a French press.
I’ve tried making my own drip coffee, but I always end up being the only one dripping (in sweat). It’s a lot of work, man! (laughs)
If you could only eat one thing for the rest of your life, what would it be?
S: Hmm… give me a minute ah. Off the top of my head, I would say either lok lok (skewers), dumplings, or sushi. But if I had to choose just one… this might be a long interview, not gonna lie (laughs).
But okay, I would say either lok lok or a nice bowl of Peranakan laksa with cockles—easily the quickest way to my heart (laughs).