Drake Drops Surprise Songs "When to Say When" & "Chicago Freestyle"

Fatima Barrie

Drake shared two new songs on Saturday night, paired with a music video.

(AllHipHop News) Drake surprised fans with the release of two brand new songs on Saturday night entitled, “When to Say When” and “Chicago Freestyle”.

The release of the songs also came in the form of a music video directed by Theo Skudra.

Sampling Jay-Z’s “Song Cry,“ “When to Say When” features shots of Drake outside of Marcy Projects in Brooklyn, which went viral on social media days before.

In the “Chicago Freestyle” portion of the video which features vocals by R&B singer Giveon, clips of Drake’s million-dollar home is captured. On the song, Drake interpolates Eminem’s “Superman."

The full version of each song can be heard on Drake’s October's Very Own SoundCloud page. “When to Say When” and “Chicago Freestyle,” are the first solo songs the rapper, singer, and actor has released since the drop of "The Best in the World Pack" last year. The two-pack features “Omertà” and “Money in the Grave” with Rick Ross.