Drake dropped two new songs without warning on Saturday, February 29th. He didn’t stop at just tracks though, he released a new music video that combined “When To Say When” and “Chicago Freestyle.” The lyrics of “When To Say When” gives a look into where Drake currently is in his life. This includes fatherhood and his prosperous career. “Chicago Freestyle” speaks of the balance between a love life and being a rapper.
The combined music video for the two songs is surprisingly only between four and a half and five minutes. “When To Say When” is closer to five minutes on its own and “Chicago Freestyle” has a duration of about three and a half minutes so both songs are definitely abridged to create the music video.
Just as there are two songs in the video, there are also two backdrops. “When To Say When” takes place in New York City while “Chicago Freestyle” shows a night out in Toronto, Drake’s hometown. With two different styles showcased in the new songs, the differing scenery really fits. “Chicago Freestyle” is one of Drake’s more gentle songs with gorgeous piano and vocal breaks while “When To Say When” has a more signature rap sound.
The songs create a contrast within the video but give a good look into Drake’s life and perspectives. There’s one thing for sure and that’s that everyone will be hearing more of “When To Say When” and “Chicago Freestyle.” The only question left is will the songs drop as a combined single or will both get separate air time.