Drake Surprises With ‘When To Say When’ & ‘Chicago Freestyle’

by Colin

Drake loves surprising fans with late night drops. Keeping the streak alive last night, the 6 God dropped off two new tracks ‘When To Say When’ & ‘Chicago Freestyle.’ The first sees Drake going in over a beat that leverages the same sample as Jay-Z’s classic ‘Song Cry.’ Drake is in his pocket dropping bars over the soulful yet knocking beat. He kicks things off sharp with, “Ayy, thirty-three years, I gave that to the game/Thirty-three mil, I save that for the rain/ Five hundred weeks, I fill the charts with my pain/Five hundred mil and I fall back in the 6ix.” The subject matter is what we’ve come to expect from braggadocios bars, to shouting out his mom and his day ones. With no hook it flows like stream of consciousness that’s assured to command replays and Instagram captions.

‘Chicago Freestyle’ switches the energy taking on a darker sound palette with Giveon’s haunting vocals opening things up. Drake’s verses showcase his travels from city to city, flipping through phone to see what girls he can hit. While tracks like Jay-Z’ ‘Girls, Girls Girls’ and YBN Cordae’s ‘Locationships’ paint a vivid and fun-loving picture of hopping from girl to girl, ‘Chicago Freestyle’ feels like Drake is jaded by the experience. As he flips Eminem’s hook from ‘Superman’ singing, “But I do know one thing though/Women they come they go/Saturday, through Sunday, Monday/Monday through Sunday, yo/Maybe I’ll love you one day/Maybe we’ll someday grow/ ‘Til then I’ll sit my drunk ass on that runway/On this one way,” he seems almost bored by it all. That said, the end result still sounds beautiful and addictive, this is Drake after all.

Stream both below.

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