Chase Colman is a forty-year-old real estate agent. Kenny Colman, his aging dad, is a brash, womanizing star of the cool jazz movement of 1960s - who never quite got over his fifteen minutes of fame. Now, Chase decides that he too would like to be a jazz singer and comes home to Vancouver to train and record. Kenny is appalled. He prays his son just won't have what it takes. The film follows the pair's complicated yet intimate relationship against the backdrop of Kenny's declining health. 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. Cool Daddy's director Roger Larry crosscuts between present day and the fascinating tale of Kenny's compulsive, yet dazzling roller-coaster Jazz ride through Vegas and New York in the 1960s. Ultimately, the film showcases a man who never quite grew up, and the intricate and tangled legacy he leaves behind.