by Jessica Shelton· Published March 2, 2020· Updated March 2, 2020

Drake’s “Chicago Freestyle”, particularly the chorus as recited by Giveon, is set in Chicago. But more to the point, we are also made aware by Giveon that this track is romantic in nature. And indeed, what Drake is harping on for that most part is the transient nature of the romances he engages in, which is apparently the result of him constantly being on move. So when he does find himself back in Chi-town for instance, he may decide to hook up with a lady he’s dealt with in the Windy City on previous occasions. 

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However, he is then disappointed to find out that she has since moved on with her life and is no longer interested in hooking up. So he has his homey, Chubbs, find him a new female to spend the night with. However, Drizzy does not perceive this mode of operation as being ideal since he could end up spending a whole bunch of dough on a lady whom in actuality he doesn’t even know. And he does touch upon other topics, such as haters who are trying to build up their name by starting beef with his crew. 

But overall this freestyle is based on a notable degree of romantic discontent the rapper is subject to due to his celebrity lifestyle.

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Facts about “Chicago Freestyle”

The pre-chorus of this song is derived almost verbatim from Eminem’s classic 2002 cut, “Superman”.

The credited writers of “Chicago Freestyle” are Drake, Giveon and the track’s producer, Sevn Thomas. And this is the first time that Giveon, a singer from California, has teamed up with the Toronto-based rapper.

Drake dropped this song unannounced (along with “When to Say When”) on 1 March 2020, and at the time it does not seem to be associated with any album.