The film starts off at a 25th high-school reunion where Charlie meets up with an old friend named Max, who seems to have far exceeded his initially dismal expectations in life in almost every respect by being the kind of "Action Jackson" globe-hopping alpha male every boy dreams of becoming. Max sees Charlie is in a loveless marriage to his philandering high-school crush, raising two kids that humiliate him at every turn, is employed at a dead-end job managing an in-supermarket bank outlet, and lives a life that is in a perpetual state of stagnation -- he even drives the same car he's had since high school, and it was a lemon even then. After convincing Charlie to some out to his yacht for a weekend of fun and sun while his wife's away, Max ends up hatching a plan to fake their deaths and assume stolen new identities with some big shots who were living the high life in Puerto Rico before their untimely demise. However, with the new identities comes had guys out to get the men they're assuming to be, leading Max and Charlie to fight for their second lives.