On Saturday (1st March 2020), The "Drake" delivers a late-night surprise in the form of not one, but two new songs. "When to Say When" and "Chicago Freestyle" touch on a range of topics. Including fatherhood and 500 weeks of Billboard chart success. For “When to Say When” Drake samples a classic, “Song Cry” by JAY-Z. The beat switches up for “Chicago Freestyle” which sees Eminem’s “Superman” when he raps. Women, they come they go/Saturday through Sunday Monday/Monday through Sunday, yo. Drake set a unique example in both songs with classic lyrics.
Rather than release a music video for each song. Drake merged both the tracks into one video. That is direct by cinematographer "Theo Skudra".
The video of "Chicago Freestyle" which shows Drake driving and lounging around in his hometown. Toronto, before filling a safe with stacks of money. In the second song, he talks about lessons he's learned and mistakes he's made in previous relationships. With women, he can no longer reach.
In this song Drake raps like.. "Area code in my phone, what numbers do I still have?... Who do I know from the past?.... Hit one, she says she got a man. Hit another one it goes green. Must've changed phones on the team".
Now it is unclear whether these tracks are cuts from Drake’s upcoming album or whether they’re loosies. Indeed, both songs are on SoundCloud rather than streaming services. Although Drake's last album, "Scorpion" arrived in June 2019. Earning the rapper his eighth album on the Billboard 200. Two months later, he dropped his archival compilation album, "Care Package" which also topped the big chart.