Bill Murray may be in a film a year, but he hasn't truly starred in anything since 2005's Broken Flowers, directed by Jim Jarmusch. His constant role as someone supporting or on the periphery (see: The Darjeeling Limited or Moonrise Kingdom) had perhaps almost left audiences thinking that Murray had surrendered the leading man role for good. But with Theodore Melfi's writing and directing debut, Murray has risen from the ashes of marginal characters to give us the force of nature that is Vincent MacKenna.
Coming off as your average curmudgeon, Vincent, a longtime resident of Sheepshead Bay, takes assholery to artistic heights. When new neighbors move in next door, a single mother, Maggie (Melissa McCarthy), and her son, Oliver (Jaeden Lieberher), Vincent shows off his talents for apathy quite well. Their initial introduction gets off to a rocky start after the movers Maggie hired back into the tree on Vincent's lawn, causing a branch to fall and hit his car. This quickly invokes his ire, and prompts Maggie to assume that they'll probably have minimal dealings with one another after she pays him off for the damages.
Much to her surprise, however, her hours at work (as a CAT Scan technician) turn out to be more grueling than she thought, leaving her no choice but to leave Oliver in the so-called care of Vincent. Already a social pariah at his Catholic school, Oliver takes comfort in the strange companionship of Vincent, who takes him to his favorite local bar, in addition to the race track. Oliver's "practical" education is further improved by being introduced to a prostitute Vincent occasionally pays named Daka (Naomi Watts, who has a surprisingly effective Russian accent).
Vincent unwittingly finds himself treating Oliver like a grandson, teaching him how to fight his bully at school, which results in bloodshed on both sides, though Oliver comes out the victor. Growing ever more attached to Vincent in spite of knowing so little about him, Oliver is flummoxed to find him sprawled out on the floor of his house after not picking Oliver up from school. After suffering a stroke from the stress of losing his Alzheimer's-ridden wife, who he's been going broke to keep in an affluent retirement community, and the pressure of the various gambling debts he owes to a loan shark named Zucko (Terrence Howard), Vincent becomes an even surlier version of his former self.
Regardless of his rudeness, Oliver, Daka and Maggie work together to reinvigorate his health and take care of his home while he's in the hospital. Meanwhile, Oliver's teacher at school, Mr. Geraghty (Chris O'Dowd, the most successful graduate of The IT Crowd), has assigned a project that requires each of his students to write a report on someone they know who they think qualifies as a person with saintly qualities (ah, the benefits of Catholic school). Carefully considering Vincent's behavior, Oliver chooses him, much to everyone's simultaneous surprise and understanding.