Oliver (Jaeden Lieberher), 12, whose parents just got divorced, moves with his mother (Melissa McCarthy) next door to Vincent (Bill Murray), a cantankerous, misanthropic war veteran whose gambling obsession keeps him perpetually in debt.

When Oliver is bullied at school and loses his cell phone and house key, he knocks on Vincent's door, asking to use the phone to call his mother. Thus begins a friendship between the two, as Vincent teaches the boy all about gambling, fighting, stealing, and other important guy stuff.