Drake - "When To Say When" + "Chicago Freestyle" Feat. Giveon (Music Video)

Drake returns with a vengeance.

Drake - When To Say When

Written by: Alex

On December 25, 2019, Drake discussed the track’s title and the tone of the track during his Rap Radar Interview“The one’s that we connect on the most are the ones where i’m just giving those life talks … just to show you I can still rap.” Not too long ago a video went viral with Drake in Marcy Projects shooting a music video. On Saturday (February 29) the Toronto artist surprise released a combination music video for both “When To Say When” and “Chicago Freestyle.”

In “When To Say When,” the video begins with a shot at sampling Jay-Z’s infamous “Song Cry.” Drake shares an update on where he is in life, shoutout out his mother, son, baby mother, and people he came up with. “When To Say When” has Drake boasting about his accomplishments and reminds us how long he has been charting for — “500 weeks, I fill the charts with my pain,” he raps.

When the beat transition switches and the second verse begins, vocals from Giveon, identical to Sampha, begin with Drake at his Toronto home, The Embassy.

The second verse pays homage to Eminem’s track “Superman with a very identical flow. Drake reflects on his life, the lavish lifestyle, reflecting on his former flings, and his pursuit for new women.

The music video ends with Drake stacking up a safe with stacks of cash. Two music videos in one, two notable nods to Jay-Z and Eminem. Drake just dropped a classic.

Notable lyric: “Thirty-three years I gave that to the game / thirty-three mil, I saved that for the rain / five hundred weeks, I filled the charts with my pain / Five hundred mil and I fall back in the 6ix.”

Directed by Theo Skurda. Watch below!

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