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An illustration of rapper Checkmate, from the set of his May Flowers video shoot.

Music

Checkmate Videos “May Flowers” and “Fly & Incredible” Hit Hard

TLDR: Checkmate drops two standout visuals—”May Flowers” with Concise and “Fly & Incredible”—delivering sharp energy and depth from his Pro Game 2 album.


Vancouver legend Checkmate isn’t chasing trends. He’s too busy documenting the mindset it takes to survive—and thrive—as an independent artist decades into the game. His latest album, Pro Game 2, is backed by two new videos that give fans a closer look at the mindset and moments behind the music.

“Fly & Incredible,” a performance-driven short film shot by DizzyDlux, premiered on February 18, 2025. The video captures Checkmate alone on Vancouver’s Downtown Eastside, using stark city lights and frozen sidewalks as a kind of neon-lit confessional. This is a celebration of perseverance, of artistry rooted in reality, and of those who move fearlessly in pursuit of the fly.

Then there’s the DJ Kemo-powered “May Flowers,” with Checkmate enlisting longtime collaborator Concise. Released just days before the album dropped, this one trades starkness for movement, cutting together live performance energy with behind-the-scenes access.

It’s a love letter to fans, friends, and fellow musicians who’ve been part of the journey. The lyrics push through adversity, but it’s the camaraderie on screen that delivers the deeper message: progress doesn’t happen in isolation.

Both visuals reinforce Pro Game 2’s overarching theme—work hard, move smart, and don’t forget where you’re from. Checkmate isn’t rushing the process or chasing a wave. He’s just putting in work, staying sharp, and letting the music speak for itself.

If you’re just catching up, we recently sat down with Checkmate for a deeper dive into the mindset behind Pro Game 2, his take on the Vancouver scene, and what’s next on deck. You can read the full interview here. And if you haven’t already, now’s the time to run the album front to back—Pro Game 2 which we’ve included with the interview.

You can find Pro Game 2 on Apple Music, Spotify, and various other digital streaming platforms via Natural Game Records.

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