Songfacts®:

• Here, Drake talks about his accomplishments including his Billboard chart records and his blessings, such as his infant son, Adonis.
  
  Ayy, 33 years, I gave that to the game
  33 mill, I save that for the ring
  500 weeks, I fill the charts with my pain
  Baby mama fluke, but I love her for who she is
  
  Drake reminds us that he's spent over 500 weeks on the Billboard Hot 100. He also references Sophie Brussax, the French actress with whom he had his child.
• Drake touched on the track during his December 2019 Rap Radar interview. "The ones that we connect on most are the ones where I'm just givin' those life talks like ['When To Say When']... just to show you I can still rap," he said.
• Houston producer June James samples Jay-Z's 2001 track "Song Cry," which itself is built around Bobby Glenn's 1976 track "Sounds Like a Love Song."
• Photographer Theo Skudra directed the double-video for this song and "Chicago Freestyle." Skudra filmed the "When To Say When" portion in Jay-Z's home neighborhood of Marcy, Brooklyn.