The tracks are joined together in the form of an accompanying music video, which was directed by Theo Skudra. Drake is back as he releases ‘When To Say When’. The Canadian singer and rapper released two new songs, "When To Say When" and "Chicago Freestyle," late Saturday night. The clip also features the viral moments captured from Drake’s visit to the … OVO Bossman is out today with the release of two new tracks, taking to Soundcloud where he unveiled his “When To Say When” and “Chicago Freestyle” selections.