Drake_when_to_say_when_chicago_freestyle Apr 2026

You can find the full lyrics and music video details for Drake's "When To Say When" and "Chicago Freestyle" (featuring Giveon) via the video released in March 2020. The tracks, which appear on the Dark Lane Demo Tapes mixtape, were accompanied by a music video directed by Theo Skudra, showcasing scenes in New York and Toronto. The first track, "When To Say When," features a sample from Jay-Z's "Song Cry," while the second, "Chicago Freestyle," interpolates Eminem's "Superman" and features vocals from Giveon.