Canadian rap singer Drake has released the singles "When To Say When" and "Chicago Freestyle". The double MV composed by the two songs is directed by Theo Skudra. <When To Say When> reviews Drake ’s decades in the music scene, commenting on the harvest and future expectations. In <Chicago Freestyle>, Drake reflects on his repeated fall into the wrong loop in love, with a faint sense of loneliness at night. The themes of the two songs are not the same, but both are "recalling the past life" in a slightly melancholy mood.