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Drake Drops Two New Songs, ‘When to Say When’ and ‘Chicago Freestyle’ (Watch Video)

Drake
Ollie Millington/REX/Shutterstock

Now we know what Drake was filming in Brooklyn’s Marcy Projects last month: The rapper dropped two new songs late Saturday night, “When to Say When” and “Chicago Freestyle,” which are merged into a single video. The footage, directed by Theo Skudra, was also shot in Manhattan’s Diamond district and Drake’s hometown of Toronto.

In the former, Drake references the mother of his son, Adonis (whose existence was publicly revealed by Pusha-T in 2018), by saying “Baby mama fluke, but I love her for who she is,” along with the usual bragging about his success and suffering (“Five hundred weeks, I fill the charts with my pain”).

The songs are the second to come from the rapper this year — in January he released a pair of tag-team tracks with Future, “Life Is Good” and “Desires,” although rumors of another tandem album from the pair have not yet come to pass.

The song’s Chicago segment — which was shot in Toronto — find Drake talking about touring life and how difficult it is to connect with his girlfriends in Chicago. “What numbers do I still have? / Who do I know from the past? / Hit one, she say she got a man / Hit another one, it goes green / Must’ve changed phones on the team / ‘Member when you lead me in between?”

An album is expected from Drake sometime this year. Hear the new songs below and watch the video.