Chatting with THELIONCITYBOY, or Kevin Lester as he’s sometimes known, is a little like listening to your favourite ‘cher. He knows what he’s talking about ‘cause he’s been through it before, and it’s easy to listen to him ‘cause he keeps it real.
From his struggles in the past to stay true to himself, to his infectious passion and love for music, THELIONCITYBOY’s story is one of hard work, courage and unreserved honesty.
Get to know him as we did through his journey of feeding his ambition.

When you were little, did you dream of becoming a rapper?

“Growing up, I never imagined I would be blessed to lead this extraordinary life as a rapper in Singapore. I mean, my dad would always play host to big family gatherings over the weekend in our four-room flat in Ang Mo Kio and there would be tons of singing and dancing, but I never thought music would be a career for me.”

So when did you start thinking of music as a career?

“I was always around at gigs, a fan of the local scene, following rap acts like Sheikh Haikel and bands like The Great Spy Experiment, and even attending breakdance battle events. It gave me an insight on how music could help me express my ideas and thoughts.

Was somewhere in 2009 in a band and experimenting with my own recordings, releasing solo mixtapes, when I felt like I wanted more – to tour, to play on big festival stages at SXSW, that kind of thing, and I knew to achieve that, I had to take my career seriously. It suddenly felt like a calling.”

When did becoming a rapper start to feel less like a daydream and more like a real ambition you had to fulfil?

“In 2013, I got signed to a label in LA owned by Apl De Ap, a member of the Black Eyed Peas. As part of the Peas, Apl was a world-famous star and he wanted to give back to Southeast Asia some of the experience he’d gained, coming from the Philippines himself.

So I was a million miles from home and I cherished every moment, learning from songwriters and producers as we wrote in studios together, and meeting talent managers who gave me great insights on what it takes to be part of this music machine.

I slept in a room on the second floor of Apl’s house, a beautiful bachelor pad, and every day on my way to breakfast, I would pass a glass cabinet. It was filled with tons of awards, but the one I wanted to hold so badly was the Grammy. It was within reach. I stared at it every day man, dreaming of the day I would earn one. FOR REAL.”

Did your family members have any doubts about your choice of career?

“Only you know why you’re chasing dreams. They are only yours after all. It wasn’t anyone’s fault if they didn’t get my plan or understand my journey. I had to prove to them that it was going to work.

I think I did break my mum’s heart after graduating from poly and getting accepted into uni, and all that talk about wanting to be an engineer or a pilot. I told her I was going to be a rapper. That’s crazy talk pre-YouTube and with little or no infrastructure in Singapore to follow. Would’ve been easier if I had told her I was going to play the recorder professionally.”

Along the way, you had some experiences that were less than encouraging. Do you mind sharing what some of them were like?

“I failed so many times and I’m still learning from some difficult decisions I made. In the early days, I had it all – I choked onstage in rap competitions, forgot lyrics at performances, had the sound system malfunction while standing before hundreds of people. At times, I felt like the moment got the best of me and it was another ‘L’, but it’s part and parcel of the journey. It shapes you as an artist, but you have to learn fast and correct those mistakes. You always need to present yourself in the best way possible.”

“Even if it’s staring at the paper or laptop screen for an hour and only getting three or four really good lines, that’s a step closer to a better song, a better artist or even earning that Grammy I saw out in LA.”

What pressures around drugs did you face?

“In Singapore, it never occured to me once to do it out of peer pressure, because I had family members who went in and out of jail for drug use. So from an early age, I knew that using drugs wasn’t a choice at all.

When I was out in LA, everyone was smoking weed, eating edibles or whatever. It’s part of their environment and their working style. I was around it every day. Alone, and eager to impress and fit in with all these talented artists, I didn’t want to be THAT GUY that couldn’t hang out.”

What was going through your mind mostly during that time?

“I felt not in control obviously but more importantly it felt like I was trying to be someone else. People started to like me because I was ‘cool’ or at least, I was hoping they thought that way. I think my insecurities would be the loudest in my head after all that high wore off, like why was I not more sure of myself to say no, and am I not good enough with my craft to let that shine first?”

Were they people you knew personally?

“Yes and no. It’s almost like you’re now in a circle and everyone thinks you’re comfortable sharing a joint. Wherever, during recording sessions or just at parties, I’d smoke with anyone.”

So how did you convince yourself to fight the temptation?

“I realised that I was privileged to be in a position any artist from Singapore would dream to be in. Sitting with Chris Brown’s writers, the next big pop artist, talent managers, industry pros, meeting music heroes of mine, I wasn’t going to let myself throw it all away. Losing myself to the moment with more drug use, that’s not the artist I wanted to be.”

“I think my insecurities would be the loudest in my head after all that high wore off, like why was I not more sure of myself to say no, and am I not good enough with my craft to let that shine first?”

Some entertainers feel that taking drugs helps them perform better onstage. Given your experiences, what are your thoughts on that?

“I can’t speak for other artists but I rather be in control of my own destiny. This journey is already so fragile that any wasted step will set me back to start again. I’ve got no time for that. I’m hoping to be a good example to my own kids, Zola and Ari, and teach them that you don’t have to add anything to yourself to be sure of yourself.”

Does the temptation still exist for you even now?

“I look at my friends, my family, my band, my manager and the rest of the team, and I know we all depend on each other to succeed. I don’t want to let them down.”

“Only you know why you’re chasing dreams. They’re yours after all.”

So how do you feed your ambition as a rapper these days?

“I’m always writing. It’s my best medicine. Even if it’s staring at the paper or laptop screen for an hour and only getting three or four really good lines, that’s a big high for me because it’s a step closer to a better song, a better artist or even earning that Grammy I saw out in LA. I don’t ever want my music to encourage or to glamorise drug use – especially to young Singaporeans. I want to make sure I put every effort in my songwriting to share a more positive lion city.”

Are there any other factors that help you to stay focused?

“Always surround yourself with people with good energy who you can trust. This journey is often lonely because no one ever understands the challenges we go through since we all have different goals. But that’s why you need good people to keep your heart steady and your mind strong.”

What is one piece of advice you would give anyone who’s pursuing their ambition?

“Every decision you make in life has an impact on your next day. If becoming your best is important to you, then give your craft every attention it deserves. There’s too much at risk if you take drugs. In the event you have your battle, I encourage you to keep fighting to stay sober because too often, we underestimate our own potential.

Please be persistent with your efforts even on your hardest day – Singapore needs your talent and your voice to be heard, don’t lose sight of that.”

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