Maggie (Melissa McCarthy), a single mother, moves into a new home in Brooklyn with her 12-year old son, Oliver (Jaeden Lieberher). Forced to work long hours, she has no choice but to leave Oliver in the care of their new neighbor, Vincent (Bill Murray), a retired curmudgeon with a desire for alcohol and gambling. An odd friendship soon blossoms between the improbable pair. Together with a pregnant stripper, named Daka (Naomi Watts), Vincent brings Oliver along on all the stops that make up his daily routine - the race track, a strip club, and the local dive bar. Vincent helps Oliver grow to become a man, while Oliver begins to see in Vincent something that no one else is able to: a misunderstood man with a good heart.