Drake Drops Off New Two-Piece, “When To Say When” & “Chicago Freestyle”

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Alongside a Theo Skudra-directed video.

As the anticipation for Drake’s upcoming album continues mounting, the 6 God blessed fans with a special two-piece over the weekend: “When To Say When” and “Chicago Freestyle.”

While the songs are technically separate entities, they debuted as a package deal, materializing as a Theo Skudra-directed music video. The same directorial mind behind Drake’s revelatory Rap Radar interview, Theo captures Drizzy’s emotional weight and introspection through verite imagery and narratives.

From running around the 6 to paying homage to JAY Z’s humble Marcy Projects beginnings, Drake continues invoking excitement and curiosity for the official Scorpion follow-up. 

Consistent with his past, Drake also used “Chicago Freestyle” as an opportunity to give a relatively unknown talent, Giveon, a chance to shine, as the Long Beach-bred artist provides an enchanting hook — one reminscent of Sampha’s vocal stylings. 

Check out the “When To Say When” / “Chicago Freestyle” video below: