Drake delivered a late night surprise in the form of not one, but two new songs on Saturday (Feb. 29) that touch on fatherhood, his Billboard chart success and more.
In “When to Say When,” Drake offers a bit of an update on where he’s at in his life and career, bragging of bringing “a few Ws to the 6ix” and shouting out the mother of his son, Adonis (sort of: “Baby mama fluke, but I love her for who she is”). He also reminded us of his Billboard charts reign (“Five hundred weeks, I fill the charts with my pain”): he’s spent over 500 weeks on the Billboard Hot 100, with two streaks landing him on the chart for 100+ weeks each. The first lasted a whopping 431 weeks from 2009-2017; the second began in February of 2018 and continues to the most recently dated chart, meaning his second streak is currently at 109 weeks and counting.
With “Chicago Freestyle,” Drake eases into the kind of love story only a rap star can tell. Set to romantic piano and a hushed chorus crooned by Giveon (“Two-thirty baby, won’t you meet me by the Bean? / Too early, maybe later you can show me things / You know what it is, whenever I visit / Windy city, she blowing me kisses, no”), Drake rolls through touring life and describes his life on the road while trying to spend quality time with the Chicagoan object of his affection. It’s easier said than done, and he recounts how difficult it is to stay in touch with women he’s seen here (and in other cities): “What numbers do I still have? / Who do I know from the past? / Hit one, she say she got a man / Hit another one, it goes green / Must’ve changed phones on the team / ‘Member when you lead me in between?”
Instead of releasing two separate videos, he fused the new tracks into one: “When to Say When” gets a New York City backdrop, while “Chicago Freestyle” starts at dusk in his native Toronto before he heads into a night out that syncs up with the lyrics of the song.