In the movie, Murray portrays Vincent McKenna, a brash, loud, foul-mouthed man who drinks and chain-smokes. His day mostly consists of sex with a pregnant Russian prostitute named Daka (played confidently by the always wonderful Naomi Watts) along with taking trips to the race track and his local watering hole, where he gets blasted and drunkenly dances to Jefferson Airplane. The routine is monotonous, and makes Vincent’s grayed-out, beat-down image look even sadder. However, things begin to transition when a 12-year-old named Oliver (newcomer Jaeden Lieberher) and his mother, Maggie (Melissa McCarthy), move next door. In search of someone to watch her son after school, Maggie asks Vincent to play the role of babysitter, which he agrees to, but only after guilting Maggie into paying him an hourly rate. The budding relationship between the ornery sexagenarian and the precocious young child ultimately gives the film its momentum. Vincent teaches young Oliver how to fight bullies, how to gamble, what a hooker is––you know, the important things in life.
Along the way, he grudgingly learns something about himself, too: that he’s not the monstrous person
he claims to be.
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