Without warning, Drake has returned with more new, middle-of-the-night music for his fans in the form of the music video for “When To Say When” and “Chicago Freestyle.” Featuring two songs in one, the twin singles see Drake once again in his ruminative mood, rapping coolly over a pair of chilly, downtempo beats.
In the first, director Theo Skudra tracks Drake through a homage to Jay-Z’s “Song Cry” video, with Drake riding through the streets of New York, trying on jewelry at Jacob & Co., and visiting his idol’s old stomping grounds, Marcy Houses in Brooklyn. The beat is a slowed-down reproduction of “Song Cry” as well, returning Drake to his hip-hop head roots for a nostalgic moment.
Midway through, the song cuts and we get the intro to “Chicago Freestyle.” Opening on a shot of Drake’s custom Rolls Royce bonnet ornament — an owl, naturally — this half of the video is directed by Gaetan Rousseau and finds Drake hanging out with NBA player Devin Booker and recording in the studio. The lyrics recount another story of heartbreak from the 6 God, as he gets involved too far too fast and wonders whether the new woman he’s found is truly the one. Judging from the timeline he describes, she probably wasn’t but he’s stuck with her anyway. In this song, Drake pays lyrical homage to Eminem, borrowing a flow from the 2002 song “Superman.”
There’s no telling whether these are two of Drake’s infamous loose tracks or whether they’ll be on his upcoming album, which he promised will be more concise than his last few efforts.
Watch the video for “When To Say When” and “Chicago Freestyle” above.