Track of the week: ‘When To Say When’ / ‘Chicago Freestyle’


Adrianne Kristianto, Social Media Coordinator

“33 years, I gave that to the game/33 mil, I saved that for the rain,” the 6 God raps over a June James beat as he gives listeners a visual tour of Brooklyn, New York, in his latest music video. After warmly welcoming the new year with Future on “Life Is Good” and “Desires,” Drake came right back with a two-in-one, reminding fans and listeners once again that he is far from the finish line.

With more than 20 million views on YouTube and 16 million streams on SoundCloud combined in less than a month, “When To Say When” and “Chicago Freestyle” are more loosies from Drake serving as starter pieces for his upcoming blockbuster album. Directed by one of Drake’s right-hand men and OVO photographer and videographer Theo Skudra, the music video for these fused tracks took place in Brooklyn, New York, and Drake’s homeland of Toronto, Canada. Drake announced the release of these two songs as a late-night surprise on Feb. 29 to his 64.3 million followers on Instagram, prompting them to head over to OVO’s YouTube and SoundCloud page to listen to the “leaks.”

Drake gave credit for his first solo songs of 2020 to two of the most prominent, historic rappers in the game: JAY-Z and Eminem. During the music video, in the first half of the song “When To Say When,” Drake raps over a sample of JAY-Z’s “Song Cry” while wandering the streets of JAY-Z’s borough, Brooklyn. While the laid back, syncopated beat loops in the background, Drake gives listeners a quick recap of his vibrant life and career with confidence and grace; he boasts about his reign of the Billboard charts, as he’s spent 500 weeks on the Billboard 100, making him the only solo artist to surpass the Glee cast for Hot 100 Entries in history; shows love to his mother, Sandra Graham, as he has done many times before, while also taking the responsibility of “bringing a few Ws to the 6ix,” i.e. Toronto; pays respect to Lil Wayne, a virtuoso who plays a major role in Drake’s life; and displays appreciation for the mother of his child, though he thinks that she’s a “fluke.” He is simply content in life. Then the beat switches.

In “Chicago Freestyle,” Drake gives fans and listeners a tour of his palatial pad in Toronto, called “The Embassy,” as he cites the riff from Eminem’s “Superman.” Known for his delicate and raw expression of emotion, Drake discusses the classic love life of a rap star in the heavily R&B influenced song — the search for new women, the thrill of former flames and, of course, the affluent lifestyle he currently has. Though a lot of people mistake him for Sampha at first, Giveon, the rising R&B vocalist, is featured on “Chicago Freestyle,” tenderly capturing the somber mood of the song. In the music video, Drake can be seen relishing in his illustrious nightlife with his OVO partners and affiliates like the Phoenix Suns’ guards, Devin Booker and Élie Okobo. Taking fans on a nocturnal tour of “the 6ix” in his customized Rolls Royce, Drake tastefully flexes his exorbitant wealth in “Chicago Freestyle” with his close-knit comrades.

A child actor turned hip-hop megastar, Aubrey Drake Graham represents a new breed of musical artists, one that knows when and how to associate with the world. He rewrote the rules to success in the modern rap world, and everyone followed. As stated in his Christmas “Rap Radar Podcast” interview, Drake is currently working on his highly anticipated album set for release in 2020. A couple of his leaks have surfaced on social media as of recently, yet Drake still pays no attention to them.

To see the “When To When” / “Chicago Freestyle” video, click the link below.