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Drake in the When To Say When / Chicago Freestyle video
Scene from the "When To Say When / Chicago Freestyle" video

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Song of the Day: Drake surprises fans with “When To Say When / Chicago Freestyle” video

Drake made good use of an extended February by surprising fans with a new joint video for “When To Say When” and “Chicago Freestyle.”

The leap year release was directed and edited by acclaimed cinematographer Theo Skudra, shot in multiple locations and ultimately processed at FotoKem Los Angeles.

 
Song of the Day: Drake surprises fans with When To Say When / Chicago Freestyle video

Scene from the “When To Say When / Chicago Freestyle” video

While the “Chicago Freestyle” seemingly came out of nowhere, Drake initially teased “When To Say When” during his hour-and-a-half-plus long interview with Rap Radar which has been viewed over 9.1 million times since dropping in December.

“The title’s usage of a city seemingly marks a new addition to Drake’s AM/PM series, which contains similar elements. This marks Drizzy’s first addition to the mini grouping since June 2016’s ‘4PM in Calabasas,’ as he continues to revisit his past and focuses on lyricism.” – Genius

The song features Drake reflecting on various accomplishments—including an insane 500 weeks of Billboard chart success—and the clout he’s brought to Toronto since beginning his rise to super-stardom back in 2009.

In contrast, the Sevn Thomas-produced “Chicago Freestyle,” sees the OVO general reflecting on past mistakes he’s made with relationships, and the lessons he’s learned along the way. The song features Long Beach singer-songwriter Giveon, who released his new “Heartbreak Anniversary” single via Epic Records a couple of weeks ago.

 
Song of the Day: Drake surprises fans with When To Say When / Chicago Freestyle video

Scene from the “When To Say When / Chicago Freestyle” video

“When to Say When” samples Jay-Z’s famous single “Song Cry” and is produced by June James. The video features Drake in New York City in Brooklyn’s Marcy Projects, where footage of him shooting a music video was taken a few weeks ago.

“When To Say When” and “Chicago Freestyle” are currently only available on SoundCloud. Fans have been flooding social media with comments urging Drake to upload them to other streaming platforms but it’s unclear if that will happen.

Both songs could be part of Drake’s next studio album expected to drop later this year.

The joint release of “When To Say When / Chicago Freestyle” is HipHopCanada’s Song of the Day. Check out the new video below.

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