Drake Delivers On “When To Say When” And “Chicago” Freestyle

Drake releases two new shocker tracks and one of them is “When To Say When.”

Saturday late night (February 29), the OVO heavyweight surprised us with two new “leaks,” taking to Soundcloud to fulfill the event by revealing his “When To Say When” and “Chicago Freestyle” collections.


The tracks also came in form of supplementary music videos, directed by Theo Skudra, one of Drake’s favorite associate for some time now. Remarkably, the clip highlights the viral scenes taken from Drake’s trip to JAY-Z’s old stomping grounds, Marcy Houses in Brooklyn. he also visited several other places in NYC including Jacob & Co where he bought some new ice.

June James produced track “When to Say When” and “Chicago Freestyle” are Drake’s first release after his collaboration with fellow rapper Future on “Desires” and “Life Is Good”. First they released “Life Is Good” in mid-January, and they almost instantly fired up “Desires” a few days later.

Drake dropped “War” On Christmas Eve 2019, produced by UK drill producer AXL Beats. His recently released two singles with Future hints at a potential follow up to their 2015 collaboration LP titled “What a Time to Be Alive”.

Sampling Bobby Glenn’s “Sounds Like a Love Song,” which JAY-Z also used on the Mary J. Blidge feature “Song Cry,” Drizzy brags about his achievements. “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 also paid tribute to his mum Sandy Graham and a co-owner of Philadelphia 76ers Michael Rubin (“I watched Michael Rubin win a million off a couple hands”).

The beat went a bit up-tempo for “Chicago Freestyle” as the 6 God leaves to visit his home in Toronto. He showed us around in his huge mansion labeled “The Embassy” and drove around town in his Rolls-Royce. The video finishes with Drake putting some sizable amount of money in a safe. Obviously, The rapper is doing well.

New R&B vocalist named Giveon delivers the expressive hook, while Drake derives from the Real Slim Shady 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,”.

Whenever drake drops surprises like this, they are usually goo, they sometimes go ahead to take top positions on music charts.

Check out the new visual merging the two songs below.

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