Drake Drops Video for New Songs "When to Say When" and "Chicago Freestyle"

Drake shares two new songs for the weekend.

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Drake surprise drops are always good.

On Saturday night, the 6 God dropped a video for his songs “When to Say When” and “Chicago Freestyle,” which is directed by Theo Skudra.

“33 years, I gave that to the game/33 mil, I save that for the rain/500 weeks, I fill the charts with my pain/500 mil and I fall back in the 6/Finally give you n***as the space you need to exist/Michael Jackson shit, but the palace is not for kids,” he raps over the same sample used on JAY-Z’s “Song Cry."

Drake is also spotted in Marcy Projects, which explains the clip of him in Brooklyn that went viral.

When the beat switches, Drake goes over a section featuring a new R&B vocalist named Giveon.

Drake gets reflective about his life, touching on his search for new women and how many of his former flings have moved on.

“Area code in my phone, what numbers do I still have?/Who do I know from the past?/Hit one, she say she got a man/Hit another one it goes green/Must’ve changed phones on the team,” he raps.

The video ends with Drake filling up a safe with a sizable amount of money. Clearly, The Boy is doing well.

You can watch the video above and stream the songs in full below.


Drake has been teasing a new album for 2020. Before 2019 wrapped up, Drake had an in-depth conversation with the Rap Radar Podcast and spoke about how he's taking his time with his next project. "I’ll go like three weeks in between making songs, just because like I’m just kind of enjoying life. I’m enjoying living, going out with people. Investing in personal connections, and it’s just making my music better," he said.

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