TLDR: Veteran Vancouver emcee Checkmate shares insights on his latest album Pro Game 2, his approach to music and promotion, and what’s next for his brand.
There’s a certain tone in Checkmate’s voice that hasn’t changed — calm, measured, but fully locked in. It’s the same energy that helped shape Canadian hip-hop’s golden era, and it’s all over his latest work. With Pro Game 2 now on streaming — anchored by recently released visuals for “Fly & Incredible” and the powerful “May Flowers” with longtime collaborator Concise — the Vancouver emcee shows he’s not looking back, just doubling down.
We caught up with him to talk legacy, strategy, and what it means to move with intention in an era that rarely rewards patience. Check out the interview with Checkmate below, and be sure to check out the Pro Game 2 album.
Checkmate Interview
HipHopCanada: Known for dropping classics like “Would You Die” and featured on the Canadian Anthem “Northern Touch” how would you say your musical process of creating and promoting has evolved since then?
Checkmate: Great question… so much has changed in the past 25 years, with technology probably being the biggest single contributor, affecting music creation and promotion. In terms of creation, I consider the technology a tool that helps you achieve your goal. From vintage mics and outboard modules to the latest AI assisted digital platforms… it’s all the same, just make it dope.
A good song or beat is still good no matter the process.
In terms of promotion, everything changes so fast that you have to be learning all the time. Is a video still a good promotional tool? Facebook ads? TikTok short reels? Is touring effective? Depending where you are in your career and the budget you have, an artist has to make decisions each release and then evaluate whether or not your strategy is effective. You gotta love music or you won’t last long.
HipHopCanada: You participated in the opening night of OVOFest with the All Canadian Northstars. What was that experience like? and tell us how all that came together.
C: Incredible experience of course, all thanks to Drake. After all these years of writing and producing at a professional level, being acknowledged by arguably the biggest artist on the planet was truly gratifying. Also reuniting with a lot of my peers in the industry and meeting some of them in person for the first time was amazing. Great night, amazing performances, epic venue… History for real!
Basically, got a call from DJ Charlie B… it was whatever it took to get me to Toronto and get that verse off… the final verse of the whole evening! The closer! We did that!
Checkmate (Photo: DJ Kemo)
HipHopCanada: You have had the opportunity to work, record and be in the same room as some of industries most recognized names. From Kardinal To Royce Da 5’9″ What is a tip you would give to up and coming artists trying to create relations and network?
C: It’s a difficult thing, and different situations are presented to you constantly, so you have to kind of read the room. It’s always better if your reputation precedes you in a positive light. For example, if someone already knows and likes your music then that’s a layup. Be humble and courteous though… remember, these artists do not need you at all. They chose who they like.
On the other hand, be yourself. Sometimes, you’re not gonna vibe with people for one reason or another. That’s okay. Be professional. Execute your part of the agreement and remain cordial. You never know… there are many hit songs made by collaborators who did not particularly care for each other.
HipHopCanada: How has the scene in Vancouver evolved over the years? And what would you like to see more from the city?
C: It’s changed… but so has everything else in the world.
As a newer genre in the 90’s, hip-hop was on the rise… also there was no YouTube or social media. You had to buy records, cassettes or CDs.
You listened to music in the whip, at house parties, and the club. You had to be outside to catch the vibe, which caused interaction… a “scene.”
Now, hip-hop music is established and mainstream. You can conveniently stream anything for $10/month in the comfort of your own home through high quality headphones. You can comment, share and be digitally active without ever leaving your house… more people than ever consume hip-hop music of all kinds, but the idea of a scene is an outdated concept.
I would like to acknowledge the new young rappers coming out the city and the valley though… it’s just different the way we consume music now…figure it out.
Checkmate (Photo: DJ Kemo)
HipHopCanada: Over The Years We have seen numerous collaboration Albums from Defenders of The Faith (Checkmate & Concise) to Avaitor Game with Dj Kemo (Rascalz) what can we expect from your brand and what is something you have been looking forward to doing this year?
C: The catalogue is dumb right now.. “Hustle Game 101” by Checkmate & Vago (2019), “Aviator Game” by Checkmate & DJ Kemo (2021), “Advanced Game” by Checkmate & Eng (2021), “Pro Game” by Checkmate (2023), “Pro Game 2” by Checkmate (2025).
Full albums, dope artwork, crazy features including Jay Worthy, Ras Kass, Planet Asia, JD Era, Concise, Bishop Brigante (R.I.P), Moka Only, Snak The Ripper, Wizdome Bunitall, Tre Nyce, Sibbs Roc and Tiago Vasquez.
On deck… new album entirely produced by Vago… as yet untitled but probably 75% done… couple new collaborators on this one I’m geeked about.
On deck… new Defenders of the Faith album entirely produced by Eng… as yet untitled… 50% done.
Honourable mention to “Inference & Hearsay” by K-Rec / Moka Only/Checkmate released 2024.
HipHopCanada: Apart from music your an entrepreneur, what do you do to maintain focus and stay dialled into your daily routine without losing sight of what needs to be accomplished?
C: Prioritize what is important to you… for me it’s easy, my family comes first… their happiness is my happiness. After that, try to eat a healthy balanced diet… if you don’t know what that is, educate yourself. Try to get enough sleep. Keep moving… whether it be lifting weights, playing ball, hiking or taking a walk. Health is wealth.
Music is a privilege to indulge in when my obligations are fulfilled. It makes me happy and raises my quality of life. That being said… my motto is “1 day at a time.” Try your best today, some days are better than others… try again tomorrow.
HipHopCanada: How do you think your music has reflected in Van City showcasing the urban lifestyle in the westcoast over the years? any last thoughts?
C: My music has always been focused on bigger markets like Toronto, L.A and New York. Vancouver is a unique city. We love hip-hop, but we’re not American. Geographically we’re on the west coast but west coast hip-hop doesn’t dominate here. The culture was invented by black Americans but there are very few black people demographically here.
To my fans in Canada that get my vibe, you know wassup, we keep it G. To all the other artists coming out of Vancouver, find your lane and hustle hard. Peace!
