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Drake drops video for new songs “When to Say When” and “Chicago Freestyle”

The rapper paid tribute to JAY-Z and Eminem on the tracks.

March 01, 2020

Drake has shared a video for two new songs called “When to Say When” and “Chicago Freestyle.”

On Saturday night, the rapper surprised fans by dropping the Theo Skudra-directed visual, which was filmed in Brooklyn and his hometown of Toronto. On “When to Say When,” Drake notably utilizes the same sample as JAY-Z’s “Song Cry,” while “Chicago Freestyle” features a lyrical nod toward Eminem’s “Superman” and a guest spot by newcomer, Giveon.

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Previously, Drake shared the video for his AXL Beats-produced track “War” this past Christmas Eve. In January, he also released two singles with Future called “Life Is Good” and “Desires.”

Watch the video for “When to Say When” and “Chicago Freestyle,” above.

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Drake drops video for new songs “When to Say When” and “Chicago Freestyle”