We first meet Sandler’s Donny as a young boy, a hotshot preteen with a prepubescent school hallway strut. Despite his assumption that sex involves endless “handjobs,” he attracts the amorous attention of a shapely female teacher, resulting in frequent covert dalliances. When the two are exposed during a school assembly, she runs off in shame while he salutes a standing ovation from the entire school. Gaining massive tabloid fame, Donny becomes the latest in a long line of unlikely Sandler sex gods. This is what comes with superstardom.
Twenty-five years later, the well has run dry for Donny. Now a frequently drunk substance abuser, he’s bottomed out as a sullen strip club regular with no way to monetize his fifteen minutes of fame and seemingly superhuman seduction abilities. With the IRS beckoning, his savings have dwindled considerably, though his hopelessness finds salvation in his son. Long avoiding his screw-up father and having disowned his birth name of Han Solo, Todd (Andy Samberg) has become a wealthy hedge fund manager, and on the eve of a high-profile wedding, a magazine cover earns him just enough publicity to bring Dad back into the picture.
Todd, unsurprisingly, is also a dysfunctional bundle of neuroses, with an endless list of pill prescriptions and idiosyncrasies that involve showering in swim trunks and carrying an extra pair of underwear to work. His father’s return, however, is of the china shop bull variety, and only an impromptu lie passes Donny off as a lifelong friend, preserving the notion that Todd's folks have long perished in a massive explosion. As the duo struggle to preserve this illusion, Donny keeps scheming to get closer to his son, and presumably to his considerable wealth.
As a performer, the R rating feels freeing to Sandler. Long seen as a slacker manchild, Sandler has made a poor transition to adult characters. Lacking in moral conviction and/or comedic dimension, the collection of upper middle class simpletons he’s portrayed have limited one of the most popular comedians of his generation from actually creating any truly memorable characters beyond golf savant Happy Gilmore seventeen years ago. But as Donny, Sandler is a crude, sloppy, f-bomb machine, quick with a quip and bound to his own oblivious ego. In “That’s My Boy,” Sandler finally gets a chance to be an alpha male in the most basic sense, a show-stopping mischief maker not beholden to another forced romance or Screenwriting 101 diversion.
Because he’s essentially playing the straight man, Samberg finds considerably less success. One of the few potential breakout stars of the recent “Saturday Night Live” era, Samberg is a fully formed comic personality, but not necessarily an actor quite yet. Samberg’s gifts are subtle, not necessarily outsized, and while they fit into a cartoon comedic world like “Hot Rod,” they’re a more awkward fit for the down-to-earth Happy Madison universe. Bits of Samberg’s rubbery manic energy burst through the seams, mostly in the form of painful-looking pratfalls, but for the most part he feels like a polite guest in the Sandler world, too concerned with not ruffling the blankets, and, more importantly, not upstaging his more prestigious co-star.
Sandler, notorious for loading his movies with significant non-actors, goes somewhat overboard this time around. Pivotal roles are filled by the likes of New York Jets coach Rex Ryan, crooner Tony Orlando and, least effectively, Vanilla Ice. The former pop sensation, who has aged as if he’s just stepped out of a time machine, plays himself as an unemployed washout who nonetheless still carries on as if he’s got the world’s biggest chip on his shoulder. While fellow 'SNL' vet Will Forte manages to give a wickedly comic spin to the most mundane expository dialogue, and James Caan lets loose as a tough-talking priest, we get to spend an inordinate amount of time with ESPN personality Dan Patrick as a dimwitted reality TV host in a deadening, charmless characterization. You’d think these roles would be better suited to any number of Sandler’s former “SNL” mates, but no -- New York Knick Baron Davis clearly needed the work.
Most surprisingly, the R-rating gives Sandler and his cronies greater opportunities to explore his considerably backwards sexual views. Every single female character in this film, from the (typical) foul-mouthed grandmother to the random extras, is a sex object. Sandler doesn’t discriminate -- Donny’s best confidante is an overweight black stripper, and even Todd’s fiancée has her own peculiar bedroom peccadilloes, revealed in a genuinely shocking, tasteless, absurdly upsetting third act reveal. In “That’s My Boy,” our men are bound to be bad boys forever, because it’s the women that are destined to be objects of mockery, derision and even grotesque defilement. [D]