Late Saturday night, Drake dropped two songs in a brand new video. “When to Say When” and “Chicago Freestyle” were both teased as leaks via soundcloud. The two songs signal the release of Drake’s new album, which he testifies will be shorter than 2018’s Scorpion.
The former samples Bobby Glenn’s “Sounds Like a Love Song” made famous by JAY Z’s iconic “Song Cry” and is full of the punchline happy lines that have become the superstar’s signature. Drake filmed the first half of the video in Marcy Projects, the childhood neighbourhood of JAY Z, ending speculation as to why he was spending time there earlier this month.
The beat switch to “Chicago Freestyle” featuring a vocal by Giveon and a lyrical homage to Eminem’s “Superman” takes Drake back home to Toronto where his mansion called The Embassy is showcased.
The flashy video contains Jacob the Jeweller, an OVO branded Rolls Royce, shoutouts to his mother Sandy Graham and 76ers owner Michael Rubin, the Japanese Crown Musk Melon from omakase restaurant Shoushin in North York, and ends with Drake adding stacks of money to his safe. It was directed by Drake’s photographer, Theo Skudra.
Check out the must see visual below.