Drake drops video for “When to Say When,” “Chicago Freestyle”

The rapper references Jay-Z and Eminem on the new tracks.

Drake has released a double-video for his new songs, “When to Say When” and “Chicago Freestyle.”

The clip opens with gorgeous shots of the rapper exploring New York City and performing “When to Say When,” which samples Jay-Z’s 2001 track, “Song Cry.” It then abruptly cuts to Drizzy back in his hometown of Toronto for “Chicago Freestyle.” The latter track also interpolates a verse from Eminem’s 2002 song, “Superman.”

Last week, Drake revealed that his as-yet-untitled forthcoming album will be “more concise” than his 2018 double album Scorpion. He also recently teamed up with Future on the songs “Desires” and “Life is Good.”


Watch the video for “When to Say When,” “Chicago Freestyle” here:

And listen to the songs in full below.


“When to Say When”:

“Chicago Freestyle”:


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