Rapper Drake surprised his fans by dropping two new songs 'When to Say When' and 'Chicago Freestyle,' both of which have been merged into a single video.

The 33-year-old singer dropped the song in his official YouTube page in the later hours of Saturday. Clocking in at four-minutes and 41- seconds, the song 'When to Say When' with the lyrics "Thirty-three years. gave that to the game," which predominately addresses the struggle and pain for reaching success.

Two minutes int the song, the video smoothly transits to the second song 'Chicago Freestyle, a rhythmic number compared to the former.
Earlier in January Drake had teamed up with rapper Future, and released tracks like 'Life Is Good' and 'Desires.'

The official music video released on January saw the rappers not in their sassy rapping avatar but in a series of roleplay where they have taken up various occupations like garbage picker, a genius employee, a mechanic and also a drive-through worker.