Drake measures himself against former rap kings on “When to Say When” and “Chicago Freestyle” but comes up short. Why?

Drake season fast approaches and the pettiness in the air proves it. Before each album, the biggest rapper in the world must step off to the side, speak his mind, and reestablish his superiority. “Dreams Money Can Buy,” “5am in Toronto,” “Summer Sixteen,” “Two Birds, One Stone,” and “Diplomatic Immunity” all served this purpose for their respective albums; he uses these one-offs and loosies to do and say what he can’t on his blockbuster albums. In these pointed moments, he airs grievances, takes pot-shots, addresses rumors, and gives updates on the State of Drake.

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On “When to Say When” and “Chicago Freestyle,” two new songs released together, Drake explains what it’s like to have the Sword of Damocles hanging over his reign. His contemplation of his legacy is complemented by aesthetic choices that wink at his competition; the first song samples JAY-Z’s “Song Cry,” and the second interpolates Eminem’s “Superman.” Much in the vein of past Drake life talks, “When to Say When” is framed as a heart-to-heart, and he always sounds most comfortable in this mode. While he isn’t exactly JAY bringing the song to tears, his precise flow outlines the rap business and underscores his authority by leaning into his wealth as the deciding factor in any dispute (a classic JAY move). “Chicago Freestyle,” in turn, unpacks the run-of-the-mill anxieties and flexes associated with his nightlife, and Drake, who recently took his cape off, is an underrated antagonist, but he doesn’t play the heel nearly as well as ’02 Em used to.


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Neither song reaches the apex of last year’s “Omertà,” a track where Drake called Benihana pigeon food and referred to himself as just a body his brothers were living through, like some kind of owl-fitted rap messiah. The lyrical content of these two songs do not reach the heights of these vivid expressions—the closest we get to a quotable line is a moment is when Drake’s lady friend thinks that an expensive check for a dinner date must contain a typo. Drake measures himself against former rap kings on “When to Say When” and “Chicago Freestyle” but comes up short.

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