Play It Cool may refer to:

• Play It Cool (film), a 1962 British musical starring Billy Fury
• "Play It Cool" (song), by Super Furry Animals
• Play It Cool (Wilber Pan album), 2007
• Play It Cool (Lea DeLaria album), 2001
• "Play It Cool", a song by 7L & Esoteric from The Soul Purpose
• "Play It Cool", a song by George Jones from Grand Ole Opry's New Star
• "Play It Cool", a song by Grand Puba from 2000
• "Play It Cool", a song by Münchener Freiheit (band)
• "Play It Cool", a song by Ray Campi
• "Play It Cool", a song by Gangrene featuring Samuel T. Herring and Earl Sweatshirt from Welcome to Los Santos