Gh0stman’s review published on Letterboxd:
One of the great 'Florida' films and certainly a great 'crime doesn't pay' movie. While not without its own unresolved thematic contradictions (which may also be dialectical in nature), this is an intelligent and probing film that puts a filmic microscope on the American male id and its relation to consumerism/capitalism. Bay's film takes the standard power fantasies he's often been accused of pedaling (sometimes fairly, sometimes unfairly) and regurgitates it back at the audience. It's certainly an ugly, repulsive film but it's also a brutally forthright and truthful one with its sense of humor in the same key. The way it portrays class is almost downright Buñuelian, where the carefree affluent (here embodied by Shaloub, Harris, Jeong, & Rispoli) get to lord it over the have nots economically and morally while the have nots are habitually humiliated, degraded, disgraced, and shamed while also ironically being very far from undeserving of said treatment. If the main characters started off the movie with digits in their bank accounts, they wouldn't be in the predicament they would later find themselves in but they also wouldn't be any different in their character or substance. The same cannot be said about the upper class characters who are alternately bothered and tormented by them. This is a deceptively complex film, where the audience is pessimistically baited into laughing at its 'heroes' for wanting to be rich and powerful and for attempting to achieve these goals in horrible and idiotic ways but what triggers those warped desires and corrupted ambitions is the predetermined judgement the characters face at every turn; the humiliation of being poor, under-equipped, undereducated, or having been incarcerated. In no small way, Bay implicates the audience into the lives and mentalities of its inhabitants in a way that's both self-reflexive and complicitous. Pain & Gain really should've been the film that made people view Michael Bay in a different light but for some reason people still think he's America's worst filmmaker. The joke's on them and Bay is still laughing to the bank for another check and with another movie in preproduction.