Drake Drops ‘When to Say When’ & ‘Chicago Freestyle’

Drake surprised fans on Saturday night by dropping a pair of new tracks.

“When to Say When” and “Chicago Freestyle” mark his first new music of 2020 and arrive alongside a Theo Skudra-directed visual.

Over a sample of Bobby Glenn’s “Sounds Like a Love Song,” which JAY-Z sampled on “Song Cry,” Drizzy boasts about his accomplishments. “500 weeks I filled the charts with my pain / 500 mill and I’ll fall back in the 6 / Finally give you ni**as some space you need to exist / Michael Jackson shit, but the palace is not for kids,” he raps.

He also shouts out his mother Sandy Graham and Philadelphia 76ers co-owner Michael Rubin (“I watched Michael Rubin win a million off a couple hands”).

In the video, the hits up various spots in NYC including the Brooklyn Bridge and JAY-Z’s old stomping grounds of Marcy Projects. He also cops some new ice at Jacob & Co.

The beat then switches up for “Chicago Freestyle” as the 6 God heads home to Toronto. He gives a tour of his massive mansion dubbed “The Embassy” and rides around town in his Rolls-Royce with an OVO bowl in place of the Flying Spur.

Giveon provides the soulful hook, while Drake borrows from Eminem’s “Superman” in the lyrics. “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,” he raps.

He makes a stop at luxe Japanese sushi bar Shoushin, hits the studio with 40, and counts stacks of money before placing it in a safe.

The two tracks arrive ahead of Drake’s new album, which he says will be shorter than 2018’s Scorpion. “This album, I’ll probably make it a more realistic offering, something more concise,” he said during a recent Toronto Raptors game. “Anywhere, whatever you want, it can be 10, 11 songs, 16. I also do a lot of different types of music so it’s tough to make it like a seven-song album or something like that. But yeah, I’m having a lot of fun right now making music.”

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