There are two incredibly infuriating things about Adam Sandler: First, he makes movies that aren’t very good but they make boatloads of cash. Second, he could make better movies, but he chooses not to since they might not make boatloads of cash. It’s for these reasons that critics largely brush off Sandler’s movies even though they’re screened for press (which is more than I can say for the films of Paul W.S. Anderson). There are brief times when Sandler will wander off the beaten track to do something “respectable” like Funny People or Punch-Drunk Love, but everything he does feels like a cynical calculation where he’ll inevitably come back to the safe confines of a lowest-common-denominator comedy. That’s My Boy, his first R-rated feature since Punch-Drunk, shows brief glimmers of the Sandler we knew at the beginning of his film career, but those moments are drowned out by the lazy comedy for which he’s become infamous.
In 1984, young Donny Berger (Justin Weaver) has an affair with his hot teacher (Eva Amurri Martino) and gets her pregnant. The teenage father is sentenced to raise the boy while his beloved teacher serves out a 30-year jail sentence. However, Donny’s charisma makes him a huge star, and like all 80s stars who don’t die of drug overdoses, his selfish life has left present-day Donny (Sandler) destitute. Donny’s accountant (NY Jets coach Rex Ryan in a great cameo) informs the once-famous child star that he owes the IRS $43,000 and has a week to get the money or he’ll go to jail. In order to get the cash, Donny devises a plan to stage a televised reunion with his incarcerated teacher and his estranged son Han Solo (Andy Samberg), who has dropped his birth name and now goes by Todd Petersen. For extra comic shenanigans, the rich and successful Todd is about to get married, and so Donny comes along to reconnect with his boy and shake things up while Todd tries to hide the truth about his parentage.
There’s an odd message at the center of That’s My Boy, and films of its ilk. We’ve seen the well-worn story where the uptight guy needs to cut loose or he’ll lose sight of what’s important (usually family and friends), but That’s My Boy spins it to where a character has to mature by becoming immature. It’s almost zen. Todd/Han Solo is littered with neuroses, but he’s worked hard to become a successful hedge fund manager. The movie never gives any indication that Todd hates his job, and his only unhappiness seems to stem from the nagging of fiancée (Leighton Meester). Since she criticizes her future husband and comes off as slightly controlling, she’s clearly up to no good.
That’s My Boy doesn’t reek of desperation for tired tropes as much as it lazily rests on them and an R-rating. Swearing is an art form, and Sandler is doodling with crayons. When it comes non-cursing jokes, Sandler, screenwriter David Caspe, and journeyman director Sean Anders seem to be under the impression that because Donny was popular in the late 80s to mid 90s, references to the era are inherently funny. I’m not exactly sure what the joke is when everyone starts shouting “Whaaaazzzzup?”, but I’m damn sure I was done with Vanilla Ice well over a decade ago. The movie brings him in for nothing but ironic value, and as far as cameos go, it’s as weak and predictable like the majority of the film’s humor.
Of course, predictability is where Sandler draws his strength. He dons a distracting voice to play the adult Donny, he swears a lot, and beats off to pictures of Todd’s boss’ elderly mother. Sandler probably doesn’t think this brand of gross-out humor is edgy. If anything, he wants to amble on in the footsteps of more creative and daring comedians and reuse their shtick. In a bizarre and twisted way, Sandler has perfected the art of presenting the veneer of raunchy humor without going so far as to make anyone uncomfortable.
None of this is new, but That’s My Boy provides brief glimmers of the strange Sandler we saw in his early leading roles. Billy Madison and Happy Gilmore aren’t avant-garde comedies, but they feature brilliant moments of oddball humor. Sandler will never make another movie that features a piece of dialogue as brilliant as:
Mr. Madison, what you’ve just said is one of the most insanely idiotic things I have ever heard. At no point in your rambling, incoherent response were you even close to anything that could be considered a rational thought. Everyone in this room is now dumber for having listened to it. I award you no points, and may God have mercy on your soul.
Unlike Vanilla Ice in That’s My Boy, Bob Barker in Happy Gilmore was a great cameo because Barker wasn’t sadly clinging to what could charitably described as “former glory.” In that film, Sandler was willing to have disapproving Lee Trevino show up for no good reason other than that it was the basis for a funny running gag.
That’s My Boy occasionally captures that king of chaotic spirit. It’s never from Sandler, and Samberg is absolutely wasted as the straight man, but occasionally you’ll get a callback to some earlier Sandler weirdness like Blake Clark rapturously massaging his pierced nipples. Yes, it’s a joke that was used in The Waterboy, but it’s the kind of humor that became verboten in the safe confines of Sandler’s cynically-minded film career. But when Sandler’s willingness to be weird extends about as far as a silly voice, his restraint unintentionally allows someone like Milo Ventigmilia, who plays Todd’s aggressive brother-in-law-to-be, to come in and steal the show.
What makes an Adam Sandler film like That’s My Boy so bad isn’t that it’s lazy and mostly unfunny. There are plenty of lazy and unfunny mainstream comedies. Sandler’s made them before and he’ll keep making them as long as they keep crossing $100 million domestically at the box office. If there was a market for him to be strange and potentially off-putting, he would make sure all of his movies had a character being immolated only to be perfectly fine in the next scene. Instead, That’s My Boy is the reminder that while Sandler may have the reputation as one of Hollywood’s nicest guys, his movies continue to show him as one of its biggest sell-outs.