Kenny Colman is a legendary Canadian jazz crooner and perhaps the ultimate cool dad. His successes include major record deals, his own TV show, the admiration of Frank Sinatra, and gigs around the world. Kenny’s biggest worry today is not his dwindling money and health, though: it is his forty-three-year-old son Chase, who has decided to leave behind his real estate career to follow in his father’s musical footsteps. Kenny thinks his son is crazy to try his hand at show business, especially at mid-life, but he is torn between trying to help his son and trying to stop him. After years of neglect, is this the time for Kenny to finally be supportive?

The film follows the pair's tortured yet intimate relationship against the backdrop of Kenny’s declining health, and Chase’s musical aspirations. Chase, still wounded from his father’s mistreatment of him as a child, tries to resist the allure of the cool, toxic, and often destructive brand of masculinity his father still represents. Ultimately, Cool Daddy showcases a man who never quite grew up, and the intricate and tangled legacy he leaves behind.