Love, Legacy, & Lil Mont from The Ave: A Listening Session

The road to your dreams is a challenging one, full of obstacles, pitfalls, and diversions. Overcoming those difficulties is much more rewarding when you maintain your path. Enter Clairmont The Second, a young, multi-disciplinary artist from Toronto. At only 19 years of age he’s already released a handful of projects, toured with SonReal, and is touted as one of the city’s next stars. He’s been working towards this for a long time – longer than we imagined. On September 2nd we attended the listening session for his upcoming project, Lil Mont from The Ave, where we caught up with some of his friends and family. They detailed Clairmont’s progress, from a young, rapping toddler to the leader we see today.

Aysha (@aysha.beeeIMG_9932-1-2

Three years ago, I think, he followed me on Twitter. And I was like, “Oh, another Toronto rapper. Whatever.” But when I listened to his songs, he was actually pretty good. I feel like this past year he’s really found his style.

He’s starting to make different genres of music now — not just hip hop and rap. Anything he wants, he puts his mind to it. He works on it until the early hours of the morning. He doesn’t sleep until everything’s perfect. He’s taught me everything I know.

“He doesn’t sleep until everything’s perfect”

He doesn’t really pay that much attention to what other people are doing, so his mindset is all his. But it really helps him to have such driven people around him, pushing him further and keeping him on track.

He’s not a really big talker. But when you listen to his music, that’s where you get his true feelings and emotions on things.

Clair (@clairandean)IMG_9914-1-3

It’s funny to tell people my brother’s a rapper, because then they’ll go “Oh…” And I’m like, “No, but he’s good”. Because if he was shit, I would tell him.

He’ll show me something and ask, “Did you see that?” And I’m like, “No, i didn’t see that. What is that?” Then he’ll teach me about some super technical thing.

[The family] is like a little art community. We’re always asking each other, “Are you doing your stuff? You’re not doing your stuff? You gotta be doing your stuff.” It’s pretty nice. I feel very fortunate.

I remember when he was five and I thought it was super cute. Then I went to live in Quebec for four years. He sent me a video, and I was like, “Wait a second. My brother’s a rapper. What am I doing in Quebec? I need to leave now and see what he’s doing.”

He knows what he wants. For him, it has to be like this and like this, and if it isn’t he can be a little tempermental about it. But i think, even in that case, he’s mastering his own emotions to make his work.

Denz (@ireallylikedenzIMG_9927-1-2

I’ve known Clairmont since he was four years old. He was the worst kid in the world (laughs). I used to make beats with his brother, and I remember regularly telling him that when Clairmont’s mind is no longer the mind of a four-year old, it’s gonna be scary. And it happened when he was sixteen.

Fuck him (laughs). That’s my first thought. Fuck that guy (laughs). Honestly, he inspires me. One, because he does this all by himself. He’s a guy that says, “I don’t know how to mix, so I’m going to spend every day learning to be the best mixer. Oh, I don’t know how to make videos, so I’m going to research the hell out of it and become the best person to take photos and make the best videos.” He’s his own label, and the boy hasn’t even turned 20 yet. You need to run your business. You need to be able to handle every single aspect of it.


I grew up listening to hip hop in the 90s, and back then, the dream was to get signed by a label. When you get signed, you know you’ve made it. The label would handle all the stuff that happens after. You wouldn’t own anything of your own.

He’s making a lot of tough decisions that someone of his age and experience wouldn’t necessarily make. This is all a testament to hard work, perseverance, and believing in yourself. He’s the man. But fuck him, still (laughs). Let that show on the record. Take out all the stuff in the middle (laughs).

Hezi (@416hezi)IMG_9974-1-2

When I watch videos of his old performances — this was before he had the high top, when he used to have a fro and wear snapbacks to the front — he looked a lot more uncomfortable on stage. But, like, it was still good. If you listen to his old stuff and compare it to his new stuff, you hear the maturity in his voice. He’s getting more comfortable with the mic and with rapping. He started so young his voice is actually changing.

It’s the same with me. We had this track that we made in grade nine. It was me, Clairmont, and our friend, Jahail. It was the first track I was ever on, and every time we speak of progression, this song comes up. This is the first time we’ve all collabed on a track. Now all our voices have dropped. I’m telling you: if you listened to that track you wouldn’t recognize any of us. But Clairmont’s kinda always been the same person. The same core person.

The aforementioned song: Don’t Sleep On Us by Xpert Detour (Clairmont The Second, Hezi, and Jahail)

Even as an overall artist, outside of just rap, Clairmont’s more advanced than I am. Bar for bar, I don’t know, I might take him (laughs). If we’re talking about producing and mixing and shooting stuff, it’s cool to have a friend who has that much talent. I’m a competitive guy. He’s a competitive guy. It’s so hard to do everything at once, which is why I respect him so much.

We’ll just be in his basement talking about random stuff. The song from his next album that I’m on as well, Ma Homie Gawd, came out of a joke we made. We were just talking about appreciating things, and Clairmont was like, “Yo, shout out my homie God.” So we made a track out of it.

We don’t want to make stuff that’s just for this time, you know what I mean? I know with Clairmont, he always talks about how we’re not living completely off the music thing yet. We’re constantly thinking of ways we can take the next step, but still stay within ourselves. Especially as independent artists. That makes things a lot more difficult.

If we had a label, we could say “yo we’re having a listening session. Deal with that”. But because we don’t, it’s like, “Okay, I gotta get the snacks. I gotta get the people.” You gotta do everything. It’s cool though. We kinda like being independent. There’s something sweet about the hard work.

The difference between me and Clairmont though, is that for him there was never anything else; it was just that

To be honest, music wasn’t always my idea. I was more into basketball at first. But around grade 12, I started to learn things about basketball and how it works. It’s almost like learning about the music industry right? Just a lot of politics and the way things work. So I’m just like, “Yo, i dont wanna play this no more. It’s not as fun.” With music, you can go independent. How do you go independent as a basketball player? That just made me dislike it as a career. I still play it for fun.

Me and Clairmont, we’ve always been into entertainment. Even like making skits and beats in class, and writing raps and drawing and all that stuff. The difference between me and Clairmont though, is that for him there was never anything else; it was just that. It was always that.

I believe there’s a God, and I believe that God has blessed our friendship to keep it together. I moved from Toronto to Richmond Hill in the seventh grade, and that would’ve been the perfect opportunity for us to not be friends anymore. You know what I mean? Everything happens for a reason.

Clairmont’s MotherIMG_9948-1

Through the years he’s always been there; always caring, always loving, and in his own way, very strong-headed.

We’re strict on discipline. We sent him to sunday school, and we hoped his music would be along the lines of gospel. But even as he grew and did very well at school, he never wanted to go to college. He thought that he could produce better than his teachers, but we all know you need that piece of paper. So what we did was give him a year off school to see what he would do with music.

I think that his seriousness came after his accident. And after that, as he grew to 17, he wanted what he wanted. And that was to do music. He’s gonna be the best.

Theres one song that he wrote, “Hallejulah,” that I think was for us. It’s one that I really like because, yes, he could’ve died, but God has him here for a reason. He grew up in church, and knows all about having a relationship with God. But now he’s mature and he’s older, and he has to make those decisions himself. I’m praying and hoping that one day he’ll come out with a full gospel album.

We can only support him all the way. We stand with each other. He has close friends who’ve all been together since grade school.

“Hallelujah, thank you Lord,
We still alive don’t let them take what’s yours”

Clairmont’s Father (@sprliveIMG_9907-1-2

Clairmont grew up seeing me playing in church, and hearing me sing in church. And of course, he saw his brother playing drums in church, so he eventually started to play drums as well. I noticed from the time he was three or four years old, he was always into mimicking things. By the time he was 10, he was doing more rapping.

His writing now isn’t just putting rhymes together; whether it’s about school or about his neighbourhood, or it’s about racism and stigmas — he’s becoming a prophetic writer. Meaning, he’s talking about issues that are targeting young people today. That’s why it will have a legacy. It will last. I compare it to Bob Marley. He’s dead and gone over 30 years ago, but his music is still relevant today.

I guess this is from his church upbringing. That was one of the things his mother and I were concerned about. Is he going to be like regular rappers with swear words left and right? But it’s much easier for him to write the way that he writes. It’s harder for him to swear in it. His brother calls him a nerd (laughs).

“If he wants to do something, he sticks with it until the end”

When he was finishing up high school, he came to me and said he preferred not to go to college. He would prefer to pursue music. My thing was, if he’s truly a musician, and truly called to do this, then I’ll test him. I know his mother wasn’t quite keen about it. She said, “No, you have to go to college!” And I said, “No, hold on a second. I’ll give you a year. And if you don’t prove yourself in a year, you have to go to college.” This would have been two years ago.

So when he decided to go into music full-time, it wasn’t quite flowing. If he had come to me and asked to get another year, I would’ve given it to him because I could see the passion and the tenacity. He insisted that this had to work. He worked and pushed, and worked and pushed.

When he came towards the end of the year, he was a bit concerned that he wasn’t as active as he wanted to be. But in my head, I knew he had what it takes to make it. So even though his mother asked, “Is he gonna go to college?” I said, “Leave him alone. What he’s learning now he’ll never be able to learn in college.” He would not even be able to pay for it, so to speak.

IMG_9876-1The set-up for the listening session

Right now he’s the embodiment of what he wants to be. He knows what he wants. Even as we’re setting up, I know to mix one way but he wants to hear things a certain way. He knows exactly what he wants. That’s Clairmont, and I admire him for that. It’s one of the traits that I think goes through all of us, from his oldest sibling to his youngest sibling. I’ve never seen him take a detour. If he wants to do something, he sticks with it until the end. Even if it fails.

Everyone was self-taught. And I think that makes so much difference. You develop your own style, your own voice. You develop your own niche.

I told him, “Don’t match yourself with anybody. As soon as you start to compare, you minimize yourself. Everybody on this planet has a purpose. Don’t worry about them. You do what you’ve been called to do. There’s 8 billion people in this world. You’ll have your crowd. You’ll have your day.” 15 to 20 years from now his music is still going to be resonating with people.

“Having plan B not an option”

In 2010, when I heard he got hit by a car, I thought the worst. When I saw the damages to the car, I thought, “Oh my god. My son is dead.” But he only had a broken leg. A week later, when he was still in the hospital having different surgeries, I told him about a gentleman who’d barely gotten hit by a car, but fell on the sidewalk, hit his head, and then died.

I said to Clairmont, “You have a purpose. You should have been killed.” Seriously. The side mirrors were torn off. There was a huge dent in the side of the car. If you looked at it, you would not believe a 12-year-old was hit and only came out with a broken leg. I said to him, “You have been designed to stay here. You have a purpose. Find it, and push yourself.”

What he’s accomplished in two years, there are some who’ve taken 10 or 15 to achieve the same. From performing to writing to videography to editing; it was all self-taught. He read. He studied. There’s growth beyond his years.

There’s nothing you cannot do. If you like it, go after it. Because when you die, you must leave a legacy. Ask any of the siblings. It’s the same thing I’ve told all of them. Go after it, and when you die, you can say, “I was here.” You might not hear it, but everyone will know it. Bottom line.

Clairmont The Second (@ctsecondIMG_9920-1-2

I don’t know man. I don’t really think about it, because I’ve just progressed so much. I’ve been going super hard, and the reason is, I want to be better than everyone else. I remember [my parents] telling me, “I know if you really want this you’ll make something happen within a year.”

School? I don’t want to go to school. Truthfully, he can’t make me go to school because I have to sign the papers and all that (laughs).

For some people it moves a lot faster, but honestly man, I’m happy. I’m happy people are here and interested, and I’m happy they want to listen to new music.

I grew up around music. It was bound to happen. I have so many people to learn from. My dad sings really well and plays instruments, and my brother raps and produces and does all that stuff. My brother is one of the people who pushed me to go harder. He’s one of my favourite rappers. Because of him, and growing up the way i did, I was able to mould myself.

It’s cool. There’s no complex answer for that. It’s so cool. I’ve put in a lot of hard work, and people are starting to recognize it.

“For some people it moves a lot faster, but honestly man, I’m happy. I’m happy people are here and interested, and I’m happy they want to listen to new music”

Thank you to Clairmont The Second and his team for throwing this event for their fans, friends, and family. Check out the recap by Devante Mowatt below:

What are your thoughts on Clairmont’s music? Do you have a favourite song? What other upcoming artists are you excited about? Reply to our tweet below to get the conversation started:

You can find more of Clairmont The Second on Twitter and Instagram.

Lil Mont from The Ave is out now! Stream it below: