As the calendar flips to October, Drake appears to be on the brink of his next big takeover, and possibly a new Nike collab. His next album, Certified Lover Boy, should arrive very soon and we'll see if he can continue his Billboard chart dominance as he has for well over the last decade. Back in August, he released his most recent single "Laugh Now Cry Later," along with a music video that's arguably the best Nike commercial in a long time. Not only did he grab a few of his fellow Swoosh-sponsored friends for cameos, but also he lived out every sneakerhead's dreams by taking a trip through Nike World Headquarters complete with a shopping spree in the company store, where he and a female companion loaded up bags galore. 

Leading up his next album's release, he's shared multiple teasers for Nike-branded merch that includes hoodies and T-shirts emblazoned with a ski-masked cupid capable of a crime spree, caps with kisses, and even socks with a Swoosh-stamped heart. No screen-printed Gildan tees for The Boy or his fans. 

The only thing missing from the bundle might be a sneaker to complete the outfit. However, we do know that, too, is in the works. 

We recently broke the news that Drake will debut his first official Nike footwear collab, most likely an Air Force 1, sometime in early 2021. That's big considering how close he reportedly came to doing a deal with Adidas after years spent under contract with Jordan Brand. The split could've tipped the cool factor in the direction of Adidas, considering how hot Kanye West and Pharrell's lines were at the time. But, alas, Drake rapped "checks over stripes, that's what I like" on Travis Scott's 2018 hit "Sicko Mode" to let everyone know all was well between him and Nike. 

There are also two versions of an unreleased Air Jordan XI sample with snakeskin that many attribute to Drake, but we can't confirm or deny his connection to the shoe, other than he had them first.

Before the next chapter begins and a proper Drake x Nike sneaker drops we decided to take a look back at the most notable sneakers between the Canadian rap star and Jordan Brand. They include several exclusives only available to Drizzy and friends, which are customary perks associated with being one of the biggest names in music and a driver of pop culture. A handful of retail releases are sprinkled in there, too—granted, any sneakerhead who wants them had to go up against a rabid fanbase eager to get their hands on anything bearing their favorite artist's name.