Drake dropped a pair of tracks over the weekend – “When to Say When” and “Chicago Freestyle.”
In an unusual move, the Canadian rap superstar released a single video for both songs. While the “When to Say When” portion shows the rapper in New York City, Toronto is the star of “Chicago Freestyle.”
It opens with a view of Drake's hometown skyline and cuts to him pulling out of his Bridle Path mansion in a Rolls Royce. The video ends with the rapper stacking bundles of cash in a safe inside his home.
In “Chicago Freestyle,” which features vocals by Giveon, Drake raps about his life on the road and the women he has in different cities.
“Problem is, I meet a girl tonight / Then I go and treat her too nice,” he raps. “Women they come, they go.”
On “When to Say When,” Drake boasts about his success. “Five hundred weeks / I fill the charts with my pain,” he raps. “Five hundred mil / and I fall back in the 6ix.”
Toronto gets another shout-out in a verse in which Drake mentions the mother of his son Adonis. “Brought a few Ws to the 6ix / Baby mama a fluke but I love her for who she is.”
Another special woman in Drake's life also get a shout-out. "Word to Sandra Graham," he raps. "No one love you like your mother can."
Watch the video for "When to Say When" and "Chicago Freestyle" below: