“When to Say When” and “Chicago Freestyle” by Drake mark his first new music since his Future collaborations “Desires” and “Life Is Good,” and arrive alongside a Theo Skudra-directed visual.
Over a sample of Bobby Glenn’s “Sounds Like a Love Song,” which JAY-Z sampled on “Song Cry,” Drizzy boasts about his accomplishments. “500 weeks I filled the charts with my pain / 500 mill and I’ll fall back in the 6 / Finally give you ni**as some space you need to exist / Michael Jackson shit, but the palace is not for kids,” he raps.
He also shouts out his mother Sandy Graham and Philadelphia 76ers co-owner Michael Rubin (“I watched Michael Rubin win a million off a couple hands”).
In the video, he hits up various spots in NYC including the Brooklyn Bridge and JAY-Z’s old stomping grounds of Marcy Projects. He also cops some new ice at Jacob & Co.