For better or for worse, I've usually considered myself to be a fan of Sandler's films. Once every two or three Grown Ups or Jack & Jills, the man makes something downright entertaining, if not completely hilarious (His 2008 film You Don't Mess with the Zohan continues to be endlessly amusing as it frequently appears on television). However, my main interest in going to see the film wasn't Sandler this time, but rather his costar, the newest SNL vet Andy Sandberg. Sandberg has been one of my favorite performers on SNL for a very long time, and after seeing him in small supporting roles for a variety of comedies, I was interested how he would do in his first major role in a blockbuster Hollywood movie. I knew from experience that almost all films released under the Happy Madison title were more joke-based than quality filmmaking, so looking for a laugh or two, chose to see the film with the understanding it could easily be mediocre. Would the great pairing of two comedic actors who I usually enjoy make the film worthwhile? The sad answer to this question is: Not really.
That's My Boy is nothing more than the average Sandler vehicle replete with the bonus profanity, sexuality, and crudity that's allowed with an R rating. However, extra gross out humor isn't necessarily a good thing. Other than a few solid jokes involving a washed up Vanilla Ice (don't ask), most attempts at disgusting comedy fail miserably. For example, a revolting strip club where Donny (Adam Sandler) frequents is often mined for laughs, but comes off more as a depressing hell hole than anything else. I feel terrible for actress Luenell, who plays an obese stripper forced to degrade herself in the name of plain horrendous humor. There're certain jokes here which I can't possibly imagine anyone finding necessarily funny, let alone up to the standard of traditional Sandler comedy.
For better or for worse, I've usually considered myself to be a fan of Sandler's films, but for the most part this was just terrible. More depressing than funny, screenplay writer David Caspe seriously needs to examine his morals, or at least realize the misfortune of others can't carry most of a film's jokes. Other than the admittedly funny twist ending, the one thing That's My Boy can pat itself on the back for is being a little better than Jack and Jill. Even as someone who openly admits to liking Adam Sandler, this was still pretty bad.