And you thought Billy Madison was immature.
I would love to lead with a statement on the order of: “That’s My Boy is the most immature film I’ve ever seen.” Unfortunately, thanks to Bucky Larson: Born to Be a Star, TMB isn’t even the most immature film I’ve seen in the last twelve months. *sigh*
I’ll go straight to the plot because that probably says it all. An obnoxious eighth grade boy has sex with a teacher. She becomes pregnant. He becomes a local hero. The product of their union goes to the boy when the woman is sent to jail. 
Then we flash-forward in time to see how they all turned out. I spent the first hour of this film trying not to think about how heroic my own 13-year-old daughter would be if she slept with her teacher. Oh, hurl. Wrong on so many levels. The premise that allows for reasonability within this context is baffling and grotesque. Do we really think this is OK because he’s a boy and not a girl? Or that he wants it? Tell me, those cases of pedophilia within the Catholic clergy … do we champion any of the altar boys as heroes? Gee, why not? Suppose one of them wanted to have sex with a priest – would that make a difference?
But I digress. It turns out there isn’t much money in the Enquirer-related local hero business –say whatever are John Wayne Bobbit and Joey Buttafuoco up to these days? — and Donnie (Adam Sandler) needs $43 K in unpaid tax money or he’s going to jail. This isn’t an inspired plot – yes, you can go to jail for tax evasion, but the IRS is far more interested in big fish and deliberate frauds of which Donnie is neither. But hey, quibbling with this plot point is like saying the Titanic’s deck should have been painted a different color. Donnie’s estranged son Han Solo (yes, it’s a running gag) is to be wed. He now goes by Todd (Andy Samburg) and has hooked the lovely socialite Jamie (Leighton Meester). Oh look, Todd’s a success. Time for a reunion.
Naturally, the pre-wedding fun is at a kick-ass fancy-schmancy estate. Naturally, Donnie crashes the party and is invited to stay the weekend, because the wedding clearly lacked for losers. Naturally, Todd is embarrassed at introducing Donnie as his father, so he calls the dirtbag his best friend, which seems impossible – but up to this point we’ve left so little in the circle of reality, it probably isn’t right to start now. And this way, we get the solid three-way combination of stooge-among-the-socialites, idiot-father-ashamed-son-reunion, bourgeois-pre-wedding-becomes-pedestrian — lousy themes all. Themes punctuated with highlights like the incest scene, the hideous full back “New Kids on the Block” tattoo (why would you not have that removed?) scene and the touching “masturbating to grandma’s picture” scene.
And all the while Donnie treats a reunion with his son, a son he needs to keep him out of jail, as an invitation for humiliation and bullying. With fathers like you …
And there’s “Uncle” Vanilla Ice. Word.
And, of course, Adam Sandler’s character, despite being a dirtbag, is a hit with the ladies. Is Sandler really this insecure? Why does he always portray a roué of sorts? Does he feel awkward around real life women? Compound this with the fact that Donnie hangs out in strip clubs all the time and I truly question whether Adam actually understands anything about women that isn’t sexual. What am I saying, he knows all about women; he just played one.
At the end of the day, you’ve got a movie in which the dirtbag, strippers and child rapist represent the best of what’s going on. I blame you for this, Adam Sandler; go straight to Hell.
Rated R, 116 Minutes
D: Sean Anders
W: David Caspe
Genre: Fart joke
Type of person most likely to enjoy this film: Boys who spend their days thinking up metaphors for homosexuality.
Type of person least likely to enjoy this film: The gainfully employed.
